Rosebud closing to diners after nearly 50 years on Taylor, will reopen as special events ‘speakeasy’

It will be the end of an era. 

The legendary Rosebud on Taylor Italian restaurant, once the “red sauce” destination for the glitterati, glam and the mob since its opening in 1976, is planning to become a special event space in the new year.

The iconic Rosebud flagship, which gave birth over the next five decades to nine Rosebud eateries including one opening in Florida, will no longer be open to general/walk-in dining after Sunday. It will re-open the following day for special events bookings only.

“After New Year’s Eve, we will turn the place into a new concept and make it into a special-occasion place,” said Rosebud founder Alex Dana.

The working name is Rosebud: The Speakeasy, for parties of 10 to 250 people.

“It will be a ‘Joe sent me’ kind of place,” said Dana. “The place has too much history to actually close.”

And what history there was around those old tables on Taylor Street at Laflin Street, where, since 2011, there is an honorary street sign marking “Alex Dana Way.”

Rosebud was originally called Bocciola della Rose (“bud of the rose”). It quickly became a destination for everyone from Frank Sinatra to Oprah Winfrey to prime ministers!

Dana has plenty of tall tablecloth tales to tell.

“We rocked back then,” chirped Dana. “It wasn’t unusual to walk out of the kitchen to see [U.S. Sen.] Ted Kennedy at the bar; [newspaper baron] Rupert Murdoch, or sports legends Digger Phelps, Sparky Henderson and Tommy Lasorda talkin’ it up.

“We’d close up for Frank Sinatra and his crew for late night dinners when Frank would take off his jacket and tie and practically strip down to his shirt to eat the red sauce with meatballs and peppers.”

Diners were often heading to Bulls or Blackhawks games on the Near West Side, or famed music spots including the Cotton Club on Michigan Avenue in the South Loop. That closed in 2008.

“Robert DeNiro would come in to eat en route to the Cotton Club with his wife, Toukie Smith. Ditto Alex Trebeck, who also was en route to the Cotton Club. Top French chef Jacques Pepin brought in the legendary Julia Child. They all came for the red sauce.

Other actors came and told tall tales of their own.

“One night actors George Hamilton and Danny Aiello and Robert Conrad, a Chicagoan, each claimed they were a tougher guy than each other … until Archie Bunker [actor Carroll O’Connor] chimed in from another table he was tougher based on where he grew up!” Dana said.

The location was not far from Oprah Winfrey’s Harpo Studios at Carpenter and Randolph in the West Loop, which had nowhere near the number of restaurants when she began filming her show there in 1990. Oprah would send stars, staff and others Rosebud’s way.

“She once sent in Diane Keaton and Goldie Hawn and Bette Midler, who had just made a movie ‘The First Wives Club’ and wound up laughing and drinking wine and eating pasta … They were hilarious!” Dana said.

“Oprah was frequently there eating her favorite, broccoli and cavatelli. She’d send in her whole show and even sent me a love letter. Whoa!”

Mobsters, too, would take their seats at tables surrounded by dark wood-paneled walls.

“Joey ‘The Clown’ Lombardo, who liked to kid people, loved to come in and hold court, talking to people all the time,” Dana recalled. “That was before he wound up going to jail,” where he died in 2019, added Dana. 

Dana, who grew up in a restaurant family, later gave birth to the star-stopping destination Rosebud on Rush, chuckled about how in the late 1990s, Chicago’s former first lady Maggie Daley once brought in England’s Prime Minister Tony Blair to the eatery, which boasted an actual red carpet entrance. 

He wasn’t the only one to make a grand entrance.

“Actor Gene Hackman actually made an entrance [arriving] in a horse and buggy,” chuckled Dana.

But ”the wildest time” was when James “The Sopranos” Gandolfini, came to eat.

“He was so mobbed at the front door, we had to sneak him the back way upstairs into the dining room.”

Changes in the neighborhood have made it necessary to try something new, Dana said. Many of the old-school Italian joints in Little Italy have closed, replaced with a variety of new places.

“Things changed in the area during the past 50 years,” said Dana. “Industrial companies moved away, which once provided us with huge lunchtime crowds. Little Italy got smaller and many residents moved to the suburbs. Business was no longer booming.”

But rest assured, Dana said the restaurant will maintain its charm — there will be no remodeling — and will continue to serve all of its signature dishes.

“Our flagship has so much history, we are not going to close,” he said.

And all the photos of celebrities and others enjoying the red sauce — including Frank Sinatra’s — will remain on the walls.

“Those were the days,” Dana said. “What a time!”