Chicago Ald. John Hoellen (47th Ward)—a Republican reformer who represented Lincoln Square from 1947 to 1975—loved rooting out government waste. He relished a fight, particularly with The Boss, Mayor Richard J. Daley. He was always good for a snappy quote. And he hated the statue that would become his city’s most iconic piece of public art.

On July 8, 1967, a month before Pablo Picasso’s unnamed sculpture was to be unveiled in the plaza of the newly-built Civic Center (now the Richard J. Daley Center), Hoellen threw an epic hissy fit in the chambers of the City Council. He started by introducing a resolution demanding his colleagues suspend council rules and replace immediately the “rusting heap of iron” with a statue honoring Mr. Cub, Ernie Banks. When Daley and Ald. Thomas Keane (31st Ward), the administration’s floor leader, tried to proceed with other business, Hoellen whipped out a homemade helmet, “fashioned from a metal lampshade with a cardboard image of the Picasso on it” (Chicago Tribune; July 8, 1967), and paraded around the floor, screaming comments like “five stories of boilerplate” and “it doesn’t belong in our city.” 

As the council clerk attempted to enter the next resolution into the city’s record, Hoellen marched up to the mayor and deposited the helmet on his rostrum. Without hesitating, Daley tossed it on the floor next to his feet, a move that drew laughs from the gallery. Two weeks later, in an interview with the Tribune (July 30, 1967), Hoellen clarified his artistic analysis: “The statue represents the power of City Hall, stark, ugly, overpowering, frightening,” he said. “If you want to get junk [in the Civic Center plaza], get two junk automobiles that have been involved in a head-on collision on the Kennedy expressway. They’ll attract attention, but, much more important than that, they’ll create a meaningful idea. They’ll tell a powerful story.” 

Hoellen may have been the most vocal opponent of Chicago’s Picasso, presented to the public for the first time 45 years ago next month, but he wasn’t the only local frustrated with or confused by Daley’s new acquisition. Universally admired half a century later, it took time and a copyright dispute for Chicagoans to embrace fully the brooding, steel abstraction that sits in their city’s heart. Or as Hoellen later called it, "the heroic monument to some dead dodo.”

Without William Hartmann, principal at the architecture firm Skidmore, Owings and Merrill (SOM), there would have been no piece of work for Hoellen to mock. When the Public Building Commission of Chicago hired SOM (among a few other firms) to design a 31-story civic center in the city’s central business district, it was Hartmann who concluded that an attention-grabbing statue would be a suitable anchor for the spacious plaza—345 feet by 220 feet—adjoining the giant courthouse. And instead of showcasing another sober historical monument, likely with some old war hero on a horse, Hartmann dreamed big. Carrying with him the imprimatur of the culturally conservative mayor—"If you gentlemen think he's the greatest, that's what we want for Chicago, and you go ahead”—Hartmann traveled to the home of 82-year-old Pablo Picasso in the French Riviera, bearing an album of Chicago photographs and a model of their site. 

Over the next three years, whenever he was in Europe, Hartmann dropped in on the famous artist to rehash his elevator pitch and deliver an assortment of Chicago-themed gifts: a Sioux war bonnet, a White Sox blazer, a Bears helmet, a Chicago Fire Department hat, photos of Ernest Hemingway and Carl Sandburg. [1] Though Picasso had never visited the Windy City, Hartmann was charming, and the idea of creating a dramatic monumental sculpture for a major American metropolis appealed to him. Finally, in 1965, the master completed a 42-inch model based on a series of drawings he had started 35 years prior. He turned down a $100,000 from the Building Commission (a pittance for what his services would have commanded on the open market), preferring to give the design as a "gift to the people of Chicago." 

Hartmann rushed it back home, where city officials authorized SOM to investigate its practicality. The firm estimated that for $300,000, welders at U.S. Steel in nearby Gary could translate the model into a finished sculpture, clocking in at 50 feet and 162 tons. Three local foundations jumped at the opportunity to underwrite the construction. It wasn’t easy to build; a 12-man crew of iron workers pounded away for three months, “[rolling] steel to sizes which never have been rolled” (WTTW). But on August 15, the alloy sculpture was assembled at the corner of Washington and Clark, and 50,000 Chicagoans descended on the plaza to watch Mayor Daley commemorate his giant attraction. 

At the time, the AP speculated that it was the “largest crowd ever gathered to watch the introduction of a piece of sculpture.” The city, hoping to capitalize on the attention, ramped up the pageantry. There was a performance from the Chicago Symphony Orchestra, invocations from a minister and rabbi, and speeches from dignitaries like Hartmann. Daley read a telegram sent by President Lyndon Johnson [2] and Gwendolyn Brooks read a poem she wrote specifically for the occasion. [3] Then came the moment the curious crush had waited for: the mayor stepped back up to the mic, announced his administration was “[dedicating] this celebrated work … with the belief that what is strange to us today will be familiar tomorrow," and yanked off a turquoise cloth that was draping the statue. The cover snagged on its steel noise—nearly sending Daley’s press secretary into cardiac arrest—before tumbling past the marble base and onto the ground. 

There it stood, 150 feet of it, for the city and world to see. And all the crowd did, at least initially, was gasp. “The weakest pinch hitter on the Cubs receives more cheers,” Mike Royko joked in his Chicago Daily News column the next day. 

Most just didn’t know what to make of it. They’d never seen a piece of art so big, so centrally located, and so mysterious. It didn’t really look like the head of a woman, as they’d been told it would. Surveyed by reporters that day, crowd members delivered their own amateur interpretations: an Afghan hound, a rib cage and appendix, a sea horse, a character from “Kukla, Fran, and Ollie,” a baboon, a Barbary ape, an aardvark. My favorite? “Nothing, absolutely nothing” (Tribune, August 15, 1967). 

A few high-profile residents joined Hoellen’s anti-Picasso brigade. Even before the statue was unveiled, Col. Jack Reilly—the mayor's director of special events—made headlines for urging its removal. Royko, the most widely read newsman in the region, wrote a withering (and frankly philistine) column in which he described the piece as “some giant insect that is about to eat a smaller, weaker insect.” [4] Less preoccupied with its literal meaning, experts fell in love with Picasso’s design. “Like a fine bridge,” an art critic for the New York Times wrote (August 15, 1967), “it combines absolute firmness with an effect of lightness.” Time declared the acquisition “one of the most magnificent windfalls in [Chicago’s] history.” “There will come a time,” surmised James Brown IV, longtime director of the Chicago Community Trust, “when we can’t imagine anything else being in the plaza except the Chicago Picasso because it is so appropriate to the site and backdrop.” 

Brown’s intuition was right, but Chicagoans took a few years to grow accustomed to their new female. Were it not for a 1970 court decision, in which a judge determined that the statue’s copyright belonged to the public and not to the Public Building Commission, it might not have happened at all. The year before, Letter Edged in Black Press, an art publisher, filed suit against the city, arguing that it had no right to prevent merchants and artists from reproducing Picasso’s design. For those that enjoy legalese, the details of the decision are here. Essentially, the court ruled that the city—as part of its publicity blitz—had authorized the press to photograph Picasso’s model and publish those shots in newspapers and magazines without first affixing a copyright notice to the design. Because of that technicality, the Copyright Act of 1909 did not apply, and the work was tossed into the public domain. According to the Tribune’s 25th anniversary retrospective (August 14, 1992), “the sculpture's big eye and flowing mane soon found its way onto postcards and keychains.” That explosion in swag “bred familiarity, the first step toward love.” 

Indeed, it’s tough to find any Chicagoan these days who doesn’t appreciate Ald. Hoellen's “rusting heap of iron,” the city’s first piece of public art for art's sake. The steel behemoth has stood for 45 years, staring us in the face, and we keep staring back at her.  

[1] Walter Netsch, another partner at SOM, later told the Tribune (March 7, 2003) that Hartmann would consistently ask, “How are we going to amuse him?" 

[2] "You have demonstrated once again that Chicago is a city second to none."

[3] “Does man love Art? Man visits Art, but squirms/Art hurts.”

[4] Royko did conclude that the statute’s “pitiless, cold, mean” eyes effectively captured the city’s “I will get you before you will get me spirit.” So in some ways, he was a fan.

Tim Reid and Tom Dreesen were desperate as hell when they wandered into the Manhattan studio of “The David Frost Show.” It was late 1971, and the Chicago-based comedy team had been working on their act, with only modest success, for two years. They needed a break. Specifically, they needed to land an appearance before a national audience. “Television,” Ron Rapoport writes in his 2008 book “Tim and Tom,” “was the holy grail.” 

Brushed off by bookers at “The Tonight Show” down the block, the duo stormed the offices of Frost’s talent coordinator like salesmen on a cold call. There stood Ken Reynolds, an African-American from Chicago’s South Side, the duo’s home turf. They’d hit the jackpot. It took just a few minutes of small talk—mostly about mutual friends back home—and a short audition before Reynolds tossed Tim and Tom in front of the camera and let them rip. They killed.

In the days between their set and the show’s air date, Reid and Dreesen hustled like they had never hustled before, passing along the details of their upcoming showcase to everyone they knew in the industry. The former, so confident the Frost spot would generate substantial buzz, quit his day job to focus exclusively on comedy. Then the episode aired … and landed with a thud. No agents called. No club owners sent over contracts. “It was as if nobody had seen it,” Rapaport writes. “As if they had never even been on.” 

So went the career of Tim and Tom, the first interracial comedy team in U.S. history. To say their act was influential, or even popular, would be an overstatement; Reid and Dreesen’s “sure-fire, can’t-miss idea”—built on the simple premise that people should put aside their racial differences and laugh together—more or less failed. But their rocky five-year run was undeniably interesting, shedding light on race relations and the cutthroat world of show business in the early 1970s. Both members of the unlikely partnership would become bankable performers in Hollywood eventually. First, they had to take a few lumps standing side-by-side.  

----

Though they grew up 850 miles apart—Reid in segregated Norfolk, Virginia, and Dreesen in the integrated, working-class town of Harvey, Illinois—Tim and Tom’s childhoods mirrored each other in fundamental ways: both went to Catholic elementary schools, had parental figures who battled addiction (Reid’s stepfather, Dreesen’s father), and spent time living above establishments (Dreesen a bar, Reid a brothel) they were too young to enter legally. As adolescents, however, their lives diverged sharply. Inspired by a trip to see the March on Washington in 1963, Reid buckled down in high school, put himself through college at Norfolk State by waiting tables, joined the school’s nascent drama department, and landed a marketing job in Chicago with DuPont, one of the company’s first black hires. Dreesen didn’t even sniff college, having dropped out of high school at 16 after his dad’s drinking habit intensified and his family moved into a rat-infested shack (with no hot water) on the black side of town. The series of odd jobs he picked up—as a caddy, a pinsetter—didn’t pay enough to make ends meet, so he followed his older brother into the Navy before stumbling into a job as a life insurance salesman back home, one that required few tangible skills aside from charm. 

Their paths first crossed in 1969, after each joined the United States Junior Chamber in Chicago’s south suburbs, Reid because he wanted to be active in his community’s affairs and Dreesen because he thought it’d be a clever way to find potential clients. At the first meeting Reid attended, Dreesen suggested the organization launch a drug-prevention program in Harvey’s grade schools. The pitch—"open the session with music, tell a few jokes to get everybody relaxed, talk to them on their own level” (Rapoport, 67)—appealed instantly to Reid, a former thespian who had spent far too many years living with a heroin addict. After a few introductory conversations, the pair called up some local principals to schedule sessions. 

While the field was admittedly thin, it didn’t take long for Tim and Tom to establish a reputation as the hippest anti-drug crusaders in Chicago’s southland; unlike cops or other authority figures, they were laid back, relatable, and shared a natural rapport. Schools requested their services constantly. After one particularly inspired assembly, an eighth grader named Joanne Cerfuka made an offhanded suggestion that caught the men flatfooted. “You guys are so funny,” she said. “You ought to be a comedy team.” It took a few days for the idea to sink in, mostly because neither had any clue how to write a routine. “If we had known how hard it was going to be,” Reid would later tell the Tribune (October 19, 1980), “I don’t think either of us would have tried it.” But both found the prospect of a career on stage appealing, so Reid bought every stand-up album he could find, they cleared some space in his kitchen, and started experimenting. 

----

From the onset, the two men knew that race would be the predominant theme of their work—it’s what they knew and wanted to lampoon. If the act was going to work, though, they had to deal with each other on even terms—Reid wouldn’t stand for any Amos ‘n’ Andy-style minstrelsy. As one of their friends told Rapoport, “[Reid] could be laughed with, but not at.” 

Fortunately, this was an easy problem to avoid; Reid was naturally the more urbane and articulate of the two, so it made sense for him to play the “cool and collected observer of his partner’s antics” (Rapoport, 71), the Dean Martin to Dreesen’s Jerry Lewis. “Black audiences had never seen that,” Reid said, “and liberal white audiences didn’t want to see a black man playing the buffoon.” The pair’s coordinated attire—colorful dinner jackets, formal tuxedos—reinforced the balanced relationship they hoped to project.

Tim and Tom developed material remarkably quickly, some of which they would use for the duration of their run. A lot of it was broad and silly. They invented a superhero named Super Spade who fought crime alongside his sidekick, The Courageous Caucasian. They poked fun at Tom’s Italian heritage. (“Are you sure he’s not with the bossa nova?” Tim would ask of Tom’s father.) In this bit below, one of their most well-known, Reid grows increasingly frustrated with Dreesen’s “anxiety” about hanging out in black neighborhoods: 

After just a few months of writing in their spare time, Reid and Dreesen convinced the owner of Party Mart Supper Club on Chicago’s South Side to put them on the evening bill. (Dreesen had no problem approaching complete strangers, a useful quality in an industry that requires one to sell himself constantly.) And in their first professional performance, in September 1969, the nervous pair “bolted through their act as if they were double parked” (Rapoport, 76). An adult audience out for a night on the town, it turned out, was tougher to impress than teens in a classroom.  

Yet over time, they grew more comfortable with each other and with performing generally. Their relentless networking helped secure new gigs, too. A popular deejay they met at WBEE, a black radio station in Harvey, took them to Chicago-area jazz clubs, record parties, and charity functions. They hit it off with Don Cornelius and Merri Dee, two luminaries in the Chicago black entertainment business. Within a year, they made a name for themselves on the local circuit, opening for Gladys Knight and the Pips, Dionne Warwick, and Anita Bryant. They were even added to the lineup of the 1st annual Black Exposition, held before 25,000 people in the International Amphitheater and headlined by Bill Cosby. Within two, they were playing some of Chicago’s biggest supper clubs. Their following at home was strong enough that by 1973, Dreesen was able to convince club owner Henry Norton to let Tim and Tom host a comedy night at his bar, LePub, on Monday nights. Improv and sketch were thriving here, but their stand-up showcase was the city’s first.

----

Chicago, as big as it was, only contained so many stand-up venues and potential fans. To make a living full-time behind the mic, which Tim and Tom hoped to do, the team needed to get out on the road. 

Building a national brand proved more difficult than they anticipated. Finding gigs wasn’t the problem; Tim and Tom played rooms big and small, in venues as diverse as the Playboy Clubs and theaters on the southern Chitlin’ Circuit. “Whenever another act fell out, missed a plan or something, boom, we were there,” Reid remembered (Rapoport, 93). “We were the National Guard of comedy teams.” The trick was finding the right gigs. More often than other stand-ups, they’d encounter racially-hostile crowds, folks who came out just to heckle, not laugh. Bookers at top-shelf venues and television shows weren’t so eager to hire an interracial pair either, particularly one whose material was charming but never excellent. (They were relative beginners, after all.) During their five years together, the biggest paycheck the pair ever earned was $750 … split two ways. And the only album they ever recorded, 1973’s “The Classic Comedy of Tim & Tom,” didn’t sell well. Reid’s enthusiasm ultimately waned.

"The thought of a black-and-white comedy team really intrigued us,” Dreesen once told the Tribune (July 11, 1991), “so we went on the road for [five] years and bombed and struggled and bombed.” In show business, you need the right combination of talent and luck to take off. It never coalesced for Tim and Tom.

The duo had an acrimonious falling out in the mid-1970s. Reid’s attention turned to Hollywood, having forged a relationship with the connected singer and actress Della Reese. “I began picturing myself doing what they were doing,” he tells Rapoport (143), about his trips to Los Angeles, “becoming an actor more than a comedian.” In November 1974, after a painful set before four people at the Hyatt Hotel in Houston, Reid flew west for good, effectively ending the partnership. It was a difficult, albeit fruitful, decision; in his first two years, after studying at the Film Actors Workshop in Burbank, he landed a series of bit parts on television shows and movies before securing the lucrative role of Venus Flytrap on the sitcom “WKRP in Cincinnati.” He’s been acting and directing ever since. 

Dreesen took the breakup much harder. Like his partner, he picked up and moved to Los Angeles, where he struggled to develop a mainstream solo act based on his childhood in Harvey and slept in his car to save money. He sounds downright bitter in a 1975 interview with the Tribune’s Bruce Vilanch, placing blame for the group’s demise squarely on Reid’s shoulders. But Dreesen got back on his feet, too. A talent coordinator for “The Tonight Show” caught his act one night in the winter of 1975 and offered him a spot, the first of 500 television appearances he would make over the next 35 years. He parlayed that exposure into a job opening for Frank Sinatra, a high-profile gig that he held for 14 years. And he’s forgiven Reid, the man with whom he’d tried to change the face of American comedy. 

The buck stood in the doorway of the dinning room atop a thin layer of leaves. He was hulking, weighing in at 250 pounds, and looked as “natural as life.” A quail pecked at food around his hooves, unbothered by the orchestra pumping in the background or the hungry aristocrats who streamed past, gazing at the majestic animal they would consume—among many others—later that evening. They’d traveled in from Paris, New York City, Vienna, and Montreal. Game was on their minds. They were ready for “Chicago’s Greatest Feed.” [1]

Long before Charlie Trotter diced vegetables or Grant Achatz picked up a blowtorch—hell, before the railroad companies opened up the Union Stockyards--John B. Drake turned Chicago into a foodie destination. The Ohio native was an unlikely gastronome, in that he spent virtually no time in a kitchen. Instead, Drake operated hotels, originally in Cincinnati and then as steward (and eventual owner) of Chicago’s Tremont House, the city’s “first hotel of metropolitan proportions.” [2]

Between 1860 and 1880, Chicago’s population would more than quadruple, but in 1855, when Drake arrived, it was still very much a frontier town. And it was teeming with game. Hunters didn’t have to travel further than the modern city limits to find an abundant supply of wild geese, turkeys, and prairie chickens. According to Edwin O. Gale’s “Reminiscences of Early Chicago,” a local pioneer once killed a 400-pound bear that occupied a tree near where LaSalle and Adams now intersect. The Tremont’s earliest guests, from the hotel’s front steps, could even shoot shoot ducks swimming in the surrounding marshland. What better way to harness those local resources and build his reputation in a new city, Drake thought, than by hosting an elaborate dinner party for Chicago’s elite. The menu would feature the region’s finest game, in quantities and variety unavailable anywhere else—Manifest Destiny on a plate, served up by Mr. Drake.

The first meal, in 1855, drew just 40 people. But what started as a relatively modest affair grew quickly in both popularity and culinary ambition. On a Sunday afternoon in 1860, for the fifth anniversary, the proprietors of the Tremont supplied 20 different meats. In 1864, the menu featured 25 cuts. Three years later, Drake served up 26. Literally every newspaper article published about the event included a variation of this phrase: “the dinner is bigger and better than the year before.” Invitations, meanwhile, were rarely turned down. “To be invited to one of these dinners was a sign that a young man had been accepted by the business community,” writes Emmett Deadmon in his book “Fabulous Chicago” (1983). “Which in Chicago was identical with being accepted socially.”

The Great Chicago Fire of 1871 was both a blessing and a curse for Drake. Like 17,500 other buildings torched by inferno, the Tremont House burned to the ground, and its owner was able to salvage only the money from the safe and a few pillowcases full of silver before the gorgeous structure collapsed. His game dinner, scheduled for the next month, was postponed indefinitely. On Drake’s walk home, however, he passed the Michigan Avenue Hotel at Congress Street (where the Congress Hotel now sits) and noticed that it was still standing. Feeling ambitious, he strolled into the lobby, found the owner, and plopped $1,000 in cash from his moneybox on the man’s desk—enough to cover an advanced payment on the hotel’s lease and furniture. The startled hotelier, convinced the flame would engulf his property like everyone else’s, hastily drew up a contract handing control over to his competitor before fleeing to safety.

Drake was rewarded for his courage. The next morning, when he strolled down to the edge of the burned district, he found the Michigan Avenue Hotel standing along the boulevard, still untouched. Immediately, Drake renamed it the Tremont House and enlarged it by taking in some adjoining buildings. Because so few hotels were still operational, the new Tremont faced very little competition; between 1871 and 1875, Wagenknecht writes that Drake “did a rushing business.” Those new profits allowed him to purchase, in 1874, the lease of the famous Grand Pacific Hotel. They also subsidized his game dinners, a tradition he would resume at a new location—and with renewed enthusiasm—the following year. “The game dinners given heretofore by Mr. Drake at the old Tremont House was one of the features of Chicago and the West,” the Tribune wrote on November 7, 1875, “and we are glad to see he intends to keep up the custom.”

So were the lucky invitees. For 18 years, beginning in 1875, Drake threw an annual party like nothing the city had ever seen … or would ever experience again. For starters, the guest list was massive. By the mid-1880s, over 500 people routinely attended, including luminaries like former President Ulysses Grant, Gen. Philip Sheridan, and Marshall Field. Every nook and cranny of the Grand Pacific ballroom was covered in flowers, ferns, and smilax, simulating the forest from where their food was gathered. Stuffed birds and fowl were perched above the greenery, their wings outspread. Tables were set with the “daintiest of china and glass” (Tribune; November 22, 1885). A game piece and an elaborate display of confectionery served as the centerpiece. “In a conspicuous place of honor,” the Tribune noted in 1888, “was set a cute little black bear cub, harnessed in dainty scarlet ribbon, and was ridden by a squirrel which announced itself the prize ‘bare’ back rider.”

The menu was just as outrageous as the decorations. Under Drake’s exacting supervision, a well-drilled army of waiters—often more than 100—brought out course after course of the rarest meat imaginable: ham of black bear, leg of elk, loin of moose, buffalo tongue, ragout of squirrel à la Francaise, roasted Sand Peeps. Diners could sample over 40 different animals. It was an orgy of flesh, or a “saturnalia of blood,” as Stefan Bechtel writes in his new book “Mr. Hornaday’s War.” Deadmon pit it more delicately: “The standards of Chicago were those of the gourmand rather than the gourmet.”

What made the later banquets even more impressive was the increasing lengths to which Drake had to go to procure his food. Game was much more scarce in 1890 than it was in 1855, particularly in Chicago, which developed rapidly after railroad companies laid tracks around the Chicago River. Instead of hunting in his own backyard, Drake contacted suppliers by telegraph, who would then kill and ship the animals to Chicago in refrigerated locomotive cars. Each November, the meat would pour in—at great expense—from the Rockies and Catskill Mountains, the shores of the Chesapeake and the swamps of the Carolinas. “A game dinner,” a Tribune reporter noted in November 1885, “now means a great deal more than an expert shot and a good cook.”

In 1894, “with the glory of the World’s Fair full upon it,” [3] John Drake decided to discontinue his celebrated game dinner. The advance planning needed to pull all of the ingredients together was just too much for the elderly entrepreneur, who died the following November. Fifteen years later, members of the Union League Club attempted to revive the tradition, throwing a dinner for 300 men that “furnished a menu that compared favorably with those old times” (Tribune; December 9, 1909). The reboot lasted just one year. In a letter to a friend, printed by the Tribune in 1957, Drake-era regular Martha Freeman Esmond said her husband “came home somewhat disappointed,” adding that the Union League’s shindig was “a fair substitute … for those who hadn’t had that privilege” of eating with Mr. Drake.

For those who had, it was only a mediocre imitation. 

[1] New York Times; November 21, 1886
[2] “Chicago;” Edward Wagenknecht (1964)
[3] Chicago Tribune; November 14, 1894

One passenger train leaves Chicago’s Union Station at 12:35 p.m. and travels west at 85 miles per hour. Another passenger train leaves Chicago’s Union Station at 12:35 p.m., merges onto the same track, and travels at an identical speed two minutes behind the first. What happens when the lead train abruptly stops and the second doesn’t?

---

Naperville is the fifth largest city in Illinois, a giant and affluent Chicago suburb voted by Money five years ago as the second best place to live in the entire country. It’s home to well-performing schools, green space, and plenty of jobs. “It’s a suburb that does all the suburban things,” says UIC urban planning professor Robert Bruegmann, “but slightly better.”

In the mid-1940s, Naperville was vastly different. Not entirely urban or rural, its 5,000 residents worked primarily on farms or at a factory run by the Kroehler Furniture Company. There was a college on the edge of town, but no hospital. The city still hadn’t razed the Pre-Emption House—the oldest continuously operating bar in the state and a vestige of Naperville's pioneer roots. And the Chicago, Burlington, and Quincy Railroad operated tracks that ran right along 4th Avenue.

On April 26, 1946, around noon, 150 people boarded Burlington’s Advance Flyer, a nine-car “fast train” heading from downtown Chicago to Omaha and Lincoln, Nebraska. Another 175 hopped on the Oakland-bound Exposition Flyer, advertised as “The Scenic Way to California—Thru the Colorado Rockies and the Feather River Canyon by Daylight.” (The trip took two days, with stops in Denver and Salt Lake City.) At the helm of the second train was W.W. Blaine, a 68-year-old engineer who had worked 40 years at the railroad and had operated diesel locomotives since 1933, the first year they were put in service on his line. To be sure, Blaine was old for his job; the railroad’s standard retirement age was 70. But he had passed all of his signal tests and the Illinois Interstate Commerce Commission ranked Burlington first in safety every year between 1930 and 1944. The passengers on board expected a smooth, relaxing ride into the western plains.

Burlington operated three tracks just west of Chicago’s city limit; the two outside tracks were reserved for freight and commuter trains, while intercity liners used the center track. Since the pair of Flyers were scheduled to depart Chicago at the exact same time, the railroad decided to treat them as one train, letting the Advance Flyer speed along in the lead at a marginally faster pace. Everything went just as planned for about 25 minutes. And then everything went terribly awry.

The Tribune would call it a “caprice of fate” (April 26, 1946). Nobody ever figured out what actually happened. But something—a small rock, perhaps, or a piece of metal—shot out from the Advance Flyer’s undercarriage, spooking the engineer enough to force an unscheduled stop near the Naperville station. Slowing down to check the running gear so quickly after taking off was an unusual move, and the crew employed every available safeguard to protect its clients, setting the emergency control system into operation and sending flagman James Tangey out the rear car to, in his words, “try to stop the train behind us.”

That proved impossible. Blaine and his Exposition Flyer blew through both a yellow caution and red stop signal, rounded a curve, and roared past Tagney. Blaine’s fireman, a frightened man named E.H. Crayton, saw the parked train in the distance and leapt from the speeding locomotive, only to hit the ground and die instantly upon contact. Blaine stayed inside and leaned on the brake for as long as he could. A mere 90 seconds after The Advanced Flyer rolled to a stop, The Exposition Flyer—chugging along at 45 miles per hour—barreled into its caboose, tore through its roof, and “plunge[d] down with terrific force upon the very floor and trucks of the car” (Tribune). Blaine’s front wheels were sheared off by the impact. “I never heard anything like it before or since to compare it to,” Jim Dudley, then an eighth grader at a nearby school, told the Tribune in a 1988 retrospective. “It was like an explosion.”

Dust, smoke, and debris scattered across the nearby countryside. The smell of ashes hung in the air. “The scene of the disaster,” the Tribune noted later that day, “was one of twisted and gnarled confusion, with huge luxury passenger coaches strewn across torn tracks like abandoned toy trains.” For a few seconds after the collision, the passengers on board made little noise. Then the shock wore off. “A moment of tragic silence was broken,” the AP wrote, “by screams and cries for help from the dying and injured.” The rear of The Advanced Flyer absorbed the bulk of the damage—most of those sitting in the rear coach and diner car were killed straightaway. Those seated further up the train escaped the worst, but were rocked nonetheless. “Things happened so fast,” one passenger said, “that I don’t remember what happened to me. I was doubled up suddenly and my knees were pushed against my chest.”

Startled by the clamor, all 800 employees at the Kroehler Furniture factory ran out to help. So did 50 students studying at North Central College. A police officer nearby made a series of frantic phone calls, recruiting doctors, nurses, and ambulances from neighboring towns. Within a matter of minutes, a full-blown rescue crew was assembled. They worked feverishly, but the task of pulling out bodies from the wreckage proved difficult. To reach the injured and dead, the police were forced to burn through the train plates using acetylene torches; eight hours after the crash, the authorities still hadn’t cut through every upturned car.

Those that were fished out were carried into the Kroehler warehouse—set up as a temporary hospital—on mattresses, because Naperville didn’t even own stretchers at the time. Miraculously, Blaine survived, crawling out through his cab’s window before making his way to first aid, where he was treated for a skull fracture. Others weren’t so lucky. Delbert Boon, a sailor from Missouri, was rushed to a hospital in adjacent Aurora, where he sent a cryptic telegram to his parents: “Come and see me. Was in train accident.” He died 30 minutes later.

It took 27 hours to clear one of Burlington’s three tracks, and three days to remove the entirety of the rubble. Thousands of curious locals jammed Naperville’s highways and streets while crews worked to catch a glimpse of the disaster. In total, 47 people eventually lost their lives in the accident, while another 125 were injured. It was, and still is, one of the worst crashes in state history.

---

So what the hell happened? Burlington surveyed its automatic signal systems right away and found that their lights had indeed functioned properly. From his hospital bed, Blaine—charged with manslaughter by state’s attorney Lee Daniels* to ensure he appeared at an inquest—insisted he saw the yellow caution and applied his brakes at once, but couldn’t slow the train down in time because he was moving too fast and his train was too light. (The Exposition was pulling nine cars that day, instead of its usual haul of 12.)

His crew mates weren’t convinced. At a public hearing set up by Burlington officials (and assailed by Blaine’s lawyer) on April 28, a road foreman testified that he inspected the locomotive shortly after the wreck and found the brake valve in the “service” position, not the “emergency” position. The Exposition’s conductor went so far as to say he noticed “no application of brakes whatsoever.” Brakeman C.W. Norris agreed with the foreman, telling his bosses that “there was never any emergency application the day of the accident.”

To test this hypothesis, the ICC and Burlington ran a series of simulations on the Naperville track a week after the crash, using a diesel train that paralleled The Exposition in length and weight. Speeding along at 85 miles per hour, a different (and younger) engineer applied the brakes immediately when he saw the yellow light and was able to slow his train to a stop 934 feet from the rear of the standing Advance Flyer. During the final test, in which he applied both service and emergency brakes when he saw the red light, he still nearly avoided contact, stopping with the engine and just one car past the collision point. The evidence did not reflect well on Blaine.

In the end, though, the embattled engineer was absolved of major blame by both the ICC and a DuPage County grand jury. In an October verdict, the latter declined to take action against the Burlington railroad or the crews of either train, instead charging everyone involved with nine “negligent acts,” ranging from improper scheduling to poor intercommunication between conductors. Rule changes followed: the ICC mandated in 1951 that trains were only permitted to exceed 79 miles per hour if automatic train stop equipment was in place, and most rail agencies still don’t mix cars of different weights on the same train. Blaine retired shortly thereafter.

Cult street photographer Charles Cushman was on hand to document the grisly scene. His photos, along with the rest of his work, are hosted online by Indiana University. Also keep an eye out for Naperville resident Chuck Spinner’s upcoming book, which will detail the stories of the victims.

*His grandson would later serve as the Speaker of the House in Illinois.

In 1895, the famed architect Jarvis Hunt and two fellow cycling enthusiasts opened the Chicago Saddle and Cycle Club. The men “felt the necessity,” as the Chicago Tribune would later report (May 14, 1899), “of having some place where they and their friends might be able to rest after a spin without being obliged to patronize the public gardens.” They choose for their clubhouse a small patch of beachfront land near Foster Avenue on the city’s North Side, where it was “no libel to call a club there built on the lake a country club” (June 3, 1945). Four years after opening for business, Hunt designed a beautiful veranda-festooned building, which overlooked a pool, horse stables, a boat house, and a three-hole golf course. The city’s financiers and socialites who could afford memberships joined the exclusive club in droves; like many of the city’s turn-of-the-century athletic associations, it provided the 1 percent with a relaxed atmosphere for networking and seclusion from the rapidly developing city. (“Tall skyscrapers are so near,” the Tribune reporter noted in 1945, “that in the future of helicopters, it could probably not even be a landing field.”)

Louis Straub was the Saddle Club’s nighttime bartender. For 12 years, beginning in 1923, Straub would come to work after collecting delinquent bills for Commonwealth Edison during the day and sling drinks to Chicago’s rich and famous. And in the early morning hours of February 3, 1935, having closed up the Saddle Club after another night of revelry, Straub was shot seven times with a .38 caliber pistol and left for dead “crumbled in a basement closet” (UP). He was 46 years old.

Straub’s slaying, “as baffling as a modern detective thriller” (AP, February 3), was never solved. Having read through the Tribune archives, which included several lengthy front-page stories detailing the crime and subsequent investigation*, here’s what I can piece together about the night in question.

It began routinely enough. Straub left his home, at 901 W. Argyle, at roughly 6:30 p.m. He carried in his wallet $54 dollars. His 34-year-old wife Helen, a former showgirl, went to play bridge at a friend’s house. The Saddle Club’s manager, who happened to be Straub’s brother, left the premises after the departure of Luke Williams, a former college tennis star, around 9 p.m. The other employees followed, entrusting Straub to serve the only remaining party, made up of six Gold Coast residents “well known in the younger social set.” During the course of his shift, Helen called Louis three times to find out when he might finish and if he would like a ride home, a favor she offered two or three times per week. “The last time I called him,” she told police, “he said he would be ready in a few minutes as a party of young people were just leaving.”

After playing bridge and consuming somewhere between three and six bottles of beer, Helen Straub left her card game at 1:30 a.m. and dropped off two friends at their homes. (Ellen Billie Edlin, one of those two women, told police she got home around 2 a.m.) Next, Helen swung by her own apartment to pick up her “white spitz dog” and drove to the club, which was quiet and dark when she arrived. Worried that Louis’ high blood pressure might have caused him trouble, she roused the night watchman on duty, Gus Schwartz, and began searching the campus, a spot “well isolated from the eyes of the curious” by “tall trees, dense shrubbery, and a high wire fence.” At Straub’s suggestion, the pair eventually opened a first-floor door on the north end of the building, one that Schwartz was confident had been locked on his last inspection three hours prior. It wasn’t. At the end of a 25-foot hallway was a lavatory, where Helen discovered her husband's “bullet-torn body” (AP). Said Schwartz: “I felt for Straub’s pulse, but could detect none. Mrs. Straub did not touch the body. She merely looked in the doorway. Then I took her outside.” The watchman called Straub’s brother and then a doctor, who pronounced the bartender dead at the scene. At 3:15 a.m., the quartet finally alerted the police, who held Straub and Edlin in custody as material witnesses.

The cops came to several firm conclusions within the first 24 hours of their investigation. Given his attire, Straub was waiting outside (and probably smoking a cigar) as the assailant approached. Somehow, he was coaxed back into the building’s basement, where he was “sprayed with a withering fire” (February 4). Because of club rules, Straub would not have let a man into the building that late at night, particularly one he didn’t know. And it wasn’t a botched robbery; though his wallet was emptied, the club’s safe and Straub’s watch were not touched. More likely, the murder was committed by a woman who was familiar with the interior of the club and thus knew Straub personally. In other words, it was a crime of passion, or perhaps vengeance.

Helen Straub proclaimed deep love for her slain beau. “Louis was the best husband in the world,” she told police on February 5, as reported by the Atlanta Constitution. “I knew of no other women in his life. We were very happy.” But detectives unearthed several “clews”** that complicated the picture of their relationship. For starters, Schwartz testified that Straub frequently entertained ladies at the bar “during the midnight hours.” Police corroborated this fact, telling reporters on February 6 that “it was easy to discern that as a husband he may have left something to be desired.” Helen Straub, it seems, found solace among her female friends, especially Mrs. Edlin, to whom she had given a $150 watch for Christmas two months earlier. “It had been no secret among this group [of bridge players],” the state’s attorney’s office learned, “that Straub and his wife had been on the verge of a break since last summer over Mrs. Straub’s affection for Mrs. Edlin.” The Tribune added its (quaint and homophobic) two cents, writing that “this strange tangle of lives and loves … probably deserves the attention of a neurologist as well as a policeman.” Curiously, the Straubs also lived in a lavish apartment that no bartender could afford even on income from two jobs. And the pair had taken out a $10,000 insurance policy on Louis’ life that contained an indemnity clause doubling Helen’s payout in case of violent death. Obviously, seven slugs to the chest qualified.

The authorities thought, for a fleeting moment, that they had cracked the case wide open on February 7, when a taxi driver named Kenneth Colling came forward and admitted that he picked up a woman closely resembling Edlin and drove her to the Saddle Club about the time of the murder. As Colling described the sequence, he waited outside for 15 minutes as the meter ran before his fare burst out of the building, sprinted into his cab, ordered him to “get the hell out of here,” and asked to be dropped off at a bar somewhere along Argyle Street. He did what he was told. Witnesses at the watering hole Colling chose remember seeing someone purchase a pint of whisky before quickly exiting. Edlin, not-so-coincidentally, went missing the day after she was released from custody. Upon searching her apartment, investigators stumbled upon a dresser drawer that contained “a pair of women’s suede gloves, stained with some dark liquid.” This was suspicious, to say the least. Yet that promising lead, teased out before DNA testing was available, hit a dead end: when pressed, employees of the liquor store expressed confidence that Edlin was not the woman who bought their booze, and she was dismissed as a possible suspect.

Stray clues emerged over the next week. The most intriguing was a lidless brown casserole dish, filled with turkey and spaghetti, that was found in the Straubs’ apartment. The club’s chef said he had prepared the concoction so Louis could enjoy a late-night meal, but the coworker could not explain how the dish got back to Louis’ house while the bartender was still on duty. (This fascinated the city’s crime reporters, who peppered their copy with questions about the mysterious casserole, even after one of the partygoers admitted “he could not be positive that the bartender was in the club all of the time during the preceding five hours.”) During a second round of questioning, Helen Straub also divulged that she had bought a .38 caliber pistol from her father several months prior to the murder and sold it for profit to Peter Breckie, a 51-year-old electrician with whom she had carried on a decade-long extramarital relationship. She further contended that Breckie “once threatened to kill Louis so that he and I could be together.” Her suitor admitted “improprieties” but firmly denied that he had purchased any weapon, that he had it in for Louis Straub, or that he was anywhere near the Saddle Club on February 3. Brickie’s wife substantiated his alibi.

The state’s attorney didn’t know where else to look. The last Tribune story filed about the high-profile saga, datelined February 18, described how “police met blank walls at every turn in the investigation of the mysterious murder.” They couldn’t figure out who hopped into Colling’s cab, what substance was splattered on Edlin’s glove, why Straub might have allowed a woman to enter the building late at night, or how the victim maintained such an expensive home in the first place. And just like that, two weeks after the grisly crime was perpetrated, the Saddle and Cycle Club murder went cold.

There is a brief coda to the story. In September of 1936, Helen Straub and Louis’ brother Ernest entered into a civil proceeding to determine who should receive the $20,410 life insurance payout for Louis’ violent death. Attorneys representing the bartenders’ sibling set out to prove that Helen herself was the killer, calling 50 witnesses to testify. They included a neighbor who remembered seeing Helen cut Louis with a butcher knife and strike him in the head with a vase at different points in their marriage as well as a night clerk at the hotel Louis lived in as a bachelor, who said Straub told him he had survived another late-night shooting attempt at the Saddle and Cycle Club sometime in 1926. Helen even took the stand; 20 pounds heavier than when Louis died, a court reporter described her as “nervous,” adding that she “became more petulant during cross examination.” Still, in a lengthy ruling, the presiding judge freed the widow of any blame and awarded her the cash. Then, three years later, taxi driver Kenneth Colling was arrested as a co-conspirator in a robbery, having arranged the hold-up of an auditor for the Sievert Electric Company. His connection to the Straub case was never fully explored, which to these untrained eyes seems like a giant missed opportunity.

The Saddle and Cycle Club, 77 years after its veteran bartender was shot, continues to operate along Lake Michigan. In 1996, the Tribune called it “the city's last true upscale country club.” If you’ve got the money, join at your own risk.

*Every citation in this piece comes from the Chicago Tribune, between February 3 and February 18, unless otherwise noted.
**How the Tribune spelled “clues,” hilariously, in the mid-1930s.