Bobbie Arnstein's Death at the Maryland Hotel

In January, 1975, the FBI's attempt to take down Hugh Hefner's Playboy empire on drug distribution charges effectively ended with the apparent suicide of the feds' key witness, former "bunny" Bobbie Arnstein, here at the Maryland Hotel, 900 N. Rush Street (now 40 E. Delaware Place).

The Maryland Hotel was built in 1928 with 300 rooms, and immediately became one of the city's most well-known institutions. Boasting a drug store, a restaurant, and a swinging dance club, there was ceaseless activity in the building.

The basement of the Maryland in the 1950s showcased some of the top entertainers and comedians of the day in "the swingingest show in town" at the famous Cloister Inn. There were typically three nighly shows, at 10 p.m., midnight, and 2 a.m. With jazz legend Ramsey Lewis leading the house band, popular acts that played the Cloister included Duke Ellington, Anita O'Day, Damita Jo, Buddy Rich, Art Blakey, Sally Rand, Redd Foxx, and Bill Cosby. Lenny Bruce had his first Chicago engagement there before moving on to the Gate of Horn club around the corner on State and Oak streets, where he was arrested and assaulted by police. Some period ads from the 1950s, enticing clubgoers with major acts including George Carlin, Della Reese, and Jim Backus (?):

In its 1950s heyday, Rush Street was packed with upscale nightclubs, cafes, and dance halls that kept the near North side swinging. Besides the Cloister, the Bambu, the Tradewinds, Mr. Kelly's, and The Happy Medium were some of the most popular clubs, and in just about any given week, one could hear performers there who today would be considered legendary, if they weren't already then.

Over time, however, the neighborhood began a slow decline. In 1960, the owner of the Cloister Inn faced a lien on his establishment due to unpaid taxes, and he sold to a new group, which renamed the basement club "The Celebrity Lounge." Great musical acts, including trombonist Si Zentner and the King Fleming Trio continued to play the Maryland throughout the early 1960s.

By the late 1960s, however, the North Rush Street area had taken on a distinctive seediness, and the small size of the Maryland's rooms, in comparison with those of more luxurious modern hotels, made it an especially unwelcome host for business and entertainment travelers. In time, most of the rooms became occupied by long-term tenants, who paid around $175 per month. The Celebrity Lounge closed and a dirty go-go club, the Rush Over, re-opened in that space, while an oyster bar, Alfie's, inhabited the first floor restaurant space. Alfie's eventually converted to a disco in 1974, offering "Plastic hanging plants, leatherette swivel chairs, some plaid upholstery....pulsating strobe lights and a mirrored ball," in the words of the Tribune's unimpressed reviewer.

Like the old Cloister Inn, The Tradewinds and Mr. Kelly's also closed, and seedier establishments such as an adult movie house and The Candy Store -- the latter of which was a strip club and thinly-disguised brothel -- took over all along Rush during the 1970s.

Given its hopping history, minor crime was commonplace at the Maryland throughout its history. Like any hotel, it had its share of unfaithful husbands seeking assignations and petty thefts. One in particular from the "I-think-there's-more-to-the-story-than-they're-letting-on" file, as described in the December 17, 1960 Tribune:

A woman in a fur coat invaded the ninth floor room of Robert Soley, 40, in the Maryland Hotel, 900 N. Rush Street, yesterday and fled with $20....Soley, a salesman from Cleveland, told police he awoke at 6:30 a.m. to find the invader rifling through his trouser pockets. He described her as an attractive blonde.

The Maryland was also involved in two of the major criminal scandals of the 1960s and 1970s. Starting in 1966, the proprietor of Alfie's, along with several other bars, strip joints, restaurants, and theaters in the Near North district, became subject to extortion by a rogue group of Chicago police calling themselves the "vice club." Officers demanded shakedowns on the order of $300 per month in return for not framing the paying clubs for selling alcohol to minors. The scheme, involving over 40 officers, was not discovered until 1972, when it became a major embarrassment for the city.

But it was suicide that brought the Maryland national headlines in 1975. Bobbie Arnstein was one of Hugh Hefner's Playboy bunnies, and his executive assistant at the Playboy Mansion, just a few blocks north of the hotel. By this time, Hefner was spending most of his time at his Beverly Hills mansion, but the Chicago mansion still housed the headquarters for the magazine empire. In 1974, Arnstein was arrested at the mansion on cocaine distribution charges, along with her boyfriend and another friend. Based on wiretap evidence, the feds charged that the entire Playboy empire, including Hefner's declining, but still popular chains of clubs, resorts, and hotels, was fronting for a massive illegal drug distribution operation.

When Miss Arnstein was convicted in federal court and sentenced to the exceptionally lengthy punishment of 15 years of hard time, the FBI decided to offer her immunity in return for blowing the cover off the drug ring -- and putting Playboy out of business.

While free on bond and awaiting appeal, Bobbie Arnstein received word that she was about to be subpoenaed by a grand jury investigating the alleged Playboy drug distribution scheme. Facing 15 years in the slammer, or ratting our her best friends and lover(s) at the mansion, she started to become unglued. State's Attorney (and future Illinois governor) James R. Thompson didn't help her mental state when he called Arnstein to his office and attempted to turn her against Playboy with claims of unmistakable evidence that Hefner had put a contract out on her life to keep her from talking.

Thus, on January 20, 1975, Bobbi Arnstein left the home of some friends after a dinner party and checked into a top-floor room at the Maryland Hotel under an assumed name. The next day, hotel staff broke into her double-locked room to find her dead, having overdosed on a combination of barbituates, sleeping pills, and valium. She left several notes to friends, including one which declared her innocence and loyalty to Hefner:

My immediate employer, Hugh Hefner, showed courage, perhaps to his own detriment, tho I hope not, and the kind of loyalty for which I hope -- even as I write this -- he is not wrongfully punished....I am innocent...despite the perjured testimony of the government's star witness, I was never part of any conspiracy to transport or distribute the alleged drugs connected with this case.

The day after her suicide, "Hef" flew to Chicago and called a press conference where he became emotional, complaining of a government "conspiracy to get me and Playboy," and blamed Arnstein's death on Thompson's prosecutorial ardor:

If she had produced evidence against me, she would never have been indicted. She was unjustly persecuted because of her relationship to me....There was no contract on her life....This is a politically inspired witch hunt.

Despite his denial, rumors continued to swirl that Arnstein's death was not entirely a suicide, and that Hefner or someone else at Playboy had her killed to stop her from testifying. Lending credence to these inuendoes was the similar apparent suicide of another bunny the year before, which also took place under unusual circumstances. Nevertheless, there has never come forth any probative evidence that Arnstein's death was anything more than it seemed. In fact, Arnstein had attempted suicide twice before, and it seems likely that she simply had a fragile nature, pushed to the breaking point by her conviction and looming prison sentence.

Without their potential lead witness against Hefner, the government turned to the two men arrested along with Arnstein on drug charges, offering them immunity for their testimony against Hefner and Playboy. Both refused, and in December, 1975, the investigation was dropped. Nevertheless, Bobbie Arnstein's death is remembered both as a sad consequence of the hedonism of the period, and of the government's zeal to prosecute those with alternative lifestyle choices.

(pictured: Bobbie Arnstein)

By 1980, the decline of the Rush Street district was complete; it had become something of a skid row on the Northside, and the Maryland was falling apart, literally. Of the 300 rooms, only 50 were occupied in July, when the hotel was sold to a group of far-sighted investors, who renovated the buildilng, combining rooms to create 87 plush condos, and adding the distinctive bay windows visible on the bulding today. They moved the entrance around the corner to Delaware Street; the previous main entrance was on the Rush Street side, near where the entrance to the high-end fashion shop Intermix is now.

Their investment turned out well, though it took a few years. Today, the adult theaters and SRO hotels are gone from the area, replaced by couture stores like Ikram and expensive boutique hotels like the soon-to-open Elysian. There are few signs of the swinging days of the Cloister Inn and Celebrity Lounge here today. The upscale clubs two blocks north, centered around Rush and Bellevue Place (recently, though universally, known as the "Viagra Triangle" for the prevalence of graying divorced men throwing cash at bleached blondes), offer only a faint echo of those that once brought some of the greatest musicians in history to Chicago. The seediness of the 1970s and 1980s-era Rush Street can be experienced to some degree at the top end of Rush, at Division St., where streetwalkers and drug-pushers mix with boozy carousers every weekend.

The basement of 40 E. Delaware Place, where jazz once blasted from the stage at the Cloister Inn, now holds bicycle storage for the residents of the upscale condos.