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After 34 Years, Doorman at The Drake Remembers Celebrities, Changing City

By David Matthews | February 23, 2016 5:38am
 Meet three generations of Downtown doormen. 
South Shore's "Doorman family."
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DOWNTOWN — Before he was a doorman, before his son became a doorman, and decades before his grandson became a doorman, Tommy Williams inspected machines at the International Harvester factory in West Pullman.

Then the factory closed. 

The company could have transferred him to another factory in Indianapolis, but Williams didn't want to pull his children out of school or leave his family on the South Side. Instead, he walked north on Michigan Avenue from Roosevelt Road, stopping at every hotel along the way, with hopes his time in the military could land him a job in security. 

When Williams arrived at The Drake hotel off Lake Shore Drive, he told the manager he didn't need to interview anyone else. Williams got the job.

"I left it at that. I just stayed here," he said.

Williams and his Cartier glasses in a 1996 Chicago Woman article about stylish hotel employees. [Chicago Woman]

Williams, who started at The Drake in 1982, plans to retire from the hotel some time after his 34th work anniversary in May. But being a doorman isn't just a job for him, it's also the family business: His son and grandson are doormen, too.

"It’s been an interesting job because I like people," said Williams Sr., 75. "I met a lot of interesting people, and most people are really good."

At The Drake, those people included former mayors Jane Byrne and Harold Washington, as well as media stars such as Carol Marin and Oprah Winfrey. Other celebrities came to The Drake during its 1980s heyday, when Williams said the hotel at 140 E. Walton Place was "the place to be." Famous people came and went, new high-rises sprouted up along the Magnificent Mile, and Williams was there by The Drake's front door to see a city change.

Tommy Williams shares how he landed a doorman job at The Drake in 1982:

As Williams will say, a hotel doorman is like the place's second concierge, and he can't air guests' dirty laundry. But these are memories he can share: Reporters interviewing him when Sun-Times advice columnist Eppie Ledderer (also known as Ann Landers) died; Oprah coming to the hotel for breakfast when she was only known as the host of "A.M. Chicago"; and late actor Paul Newman inviting Williams' family down to the Indianapolis 500 because his partner in a racing company frequented the hotel.

"We had lunch in [Newman's] trailer," Williams said. 

Princess Diana was "the only celebrity" the hotel had to block the street for when she stayed at The Drake a year before she died. But the princess was still "very cordial" and shook the hands of the spectators that the hotel was holding back from royalty. "She was some kind of lady," Williams said.

Williams also tended bar at the Coq D'Or near The Drake's lobby, and saw "a lot of stuff going on." Williams won't say who was a jerk or got into trouble, but he was at the bar for one big occasion: Roger Ebert's wedding in 1992. 

"That was one hell of a function," said Williams' son, Tom Jr. 

Tommy Williams talks about Princess Diana's visit, bartending Roger Ebert's wedding, and other celebrities he met:

Tom Jr., 50, said the doorman profession picked him. He was 18 years old when he started valet parking at a garage down the street from where his dad worked. Valeting was a summer job while he was away from culinary school, but when a new hotel opened near the garage, Tom Jr. applied for a job in its restaurant.

"They said, 'No, buddy, we like your personality. We want you on the door,' " he explained.

Tom Jr. was the doorman at a few buildings before ending up at John Hancock Center, where he remembers actor John Candy visiting his friend Chris Farley, and Ebert rolling up in a black BMW to pick up Chaz, his future wife. Tom Jr. still valeted, too, and parked Gary Grossinger's Cadillac Eldorado enough that he ended up buying it from him. Grossinger offered him a job at a dealership in 1996, and Tom Jr. sold cars for 17 years.

The Coq D'Or opened inside the Drake Hotel the day after Prohibition was repealed in 1933. Tom Williams Sr. bartended here for decades, including one night for Roger Ebert's wedding. [The Drake]

But by 2013 the Internet had changed the auto business, and Tom Jr. reapplied to the company that first hired him as a doorman. He rotated through a few buildings before landing at the exclusive Gold Coast cooperative where he works now. There, he escorts delivery drivers into seven-figure homes and warms up cars for residents before they go out. He has keys to all their homes and all their cars. 

"It’s very rewarding because people, they rely on you, and they’re excited to see you," Tom Jr. said. "It becomes part of your family once you get tenure at a particular building, because they don’t like change."

Listen: Tom Jr. describes how the doorman life chose him: 

Williams photographed in the back of a Rolls-Royce Phantom in a 2006 Car And Driver issue. [Car And Driver]

Williams Sr. cherishes the memories he has from the door, but Chicago has changed since the '80s: New hotels got built and took business from The Drake, guests search online instead of asking the doormen where to go, and they order Ubers instead of getting the hotel to hail a cab. Men wear jeans instead of sport coats in the Coq D'Or now. 

"That's what I miss, because I'm old school — old-school service," he said. Being a doorman doesn't pay as well as the job at the factory Williams lost more than 30 years ago, but he says, "you gotta do what you gotta do." Tom Jr. calls his dad his hero. 

"The fact that we three are all doorman is pure coincidence," Tom Jr. said in an e-mail. "But it is because of Tommy Williams Sr. who paved a path of professionalism and integrity that is instilled in his family through deed and diligence that both myself and my son have careers that we are very proud of."

Tom Jr. now lives with his dad in the South Shore home where he grew up. Not long ago his 19-year-old son, Tom III (or "T3," as Junior calls him) moved out. Like his grandpa, T3 once worked at a factory, and like his dad, T3 valeted cars before landing a doorman job in Old Town a few months ago. 

"It was in the family, I gotta keep the tradition," T3 said. "I heard interesting stories, but I got a long way to go."

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