Taylor Street Archives

Nick Caruso Sr…His Way

Nick Caruso Sr…His Way


A Taylor Street Odyssey 

To begin before the beginning, Nick Caruso’s mother, Mary, was born on DeKoven Street, in Mrs. O’Leary’s cottage. It is here, in the southeast corner of the legendary Taylor Street’s Little Italy, that the Great Chicago Fire is alleged to have started. 

Nick entered what many consider to be the riskiest of all entrepreneurial ventures, the restaurant and lounge business. In doing so, Caruso traveled a road not far removed from that of other Taylor Street bred entrepreneurs. The similarity between and among these Taylor Street alumni and Richard Bach’s Jonathan Livingston Seagull was that each did it their way. For Jonathan, “becoming all that he was capable of becoming” was his inspiration for learning to soar, at 160 miles per hour, around and over cliffs that once confined him to his birthplace. Ultimately, the price Jonathan paid was an untimely death when he crashed into those same cliffs.

Excelling in a world that had been defined and shaped for us by others, Nick Caruso reached out beyond the boundaries of Taylor Street’s Little Italy to the entrepreneurial world that first encompassed Rush Street, then Las Vegas, and ultimately reaching out to the city that never sleeps, New York. A world with its own treacherous cliffs and unpredictable winds. 

Whatever it was that triggered other Taylor Street bred entrepreneurs that same “piper man” called out to Caruso. In responding, Caruso joined that elite group of residents who transcended the local tradition of aligning one’s career to neighborhood and “first ward” ties. 

During his youth, when he was not in class or playing ball, Nick could usually be found at the South Water Street Market helping his dad, Sam, with the family produce business. The entrepreneurial side of his personality developed in the hustling world of one of Chicago’s busiest marketplaces. 

One could surmise that Nick’s soft-spoken and empathetic personality would have put him at a disadvantage in the “ask for and give no quarter” culture of South Water Street. Whether it did or not, we do know that he did emerge with those traits that gained him the trust and respect of business associates far removed from South Water Street’s produce market. 

The host of friends and business associates included the likes of Tommy Lasorda (of Los Angeles Dodgers fame); George Randazzo (who participated in recognizing and honoring Caruso’s loyalty with the Salvatore Franco Award at the Italian American National Sports Hall of Fame); Frank Sinatra (including Jilly Rizzo, D’Rone and other members of Sinatra’s close-knit associates); and a host of other notables too numerous to mention. 

Not to be misled by the young Caruso’s obedient responses of a son to his father’s needs and wishes, stories abound about escapades reminiscent of growing up on Taylor Street. Having a driver’s license at age 14, Caruso was in demand by his boyhood friends. Joy rides were accomplished by pushing the targeted cars out of their garages so as not to alert the owners by starting the engines too close to their homes. Ditto when they returned the cars to their garages later that same day. Needless to mention, there were many other instances that reflect the adventurous and mischievous part of “growing up Taylor Street.” 

His athletic talents and leadership skills offer yet another dimension of him. St. Ignatius, the prestigious college prep school, which anchors the south end of Taylor Street’s Little Italy, preserves in its trophy case, for posterity, a reminder of Caruso’s athletic abilities. As the starting guard, he led their basketball team to the co-championship of the City of Chicago’s catholic school athletic conference. His genetic link to Giuseppe Paolo DiMaggio, the great Joe DiMaggio, apparently had not lain dormant. The Carusos and the DiMaggios, sharing the same blood lines, emigrated from Sicily to America at the turn of the 20th century. One eventually settled in a west coast fishing village with “tiny cable cars” and the other immigrated to the city that anchored the “breadbasket” of the world.”

Other, not so visible, qualities that he possessed were apparently recognized by his high school teammates long before he made his entrance into the entrepreneurial world of Chicago’s Rush Street. His teammates elected him as their team captain. 

Nick, contrary to the path followed by most of Taylor Street’s first and second generation Italian Americans, graduated from high school and went on to attend Loyola University. His employment as an instructor at both Sheridan Park and the CYO, two of the institutions that anchored the Taylor Street community, followed shortly after his tenure at Loyola University. Both institutions complemented the now legendary Jane Addams’ Hull House in serving the needs of its Taylor Street residents. (Hull House and its summer camp, the Bowen Country Club, are memorialized elsewhere in these Archives.)

The defining moment, of the business enterprise Nick Caruso was to lead, came in 1971, when he met for the first time with Jilly Rizzo, Sinatra’s best friend and bodyguard, at Caesar’s Palace in Las Vegas. Over the years, there were frequent consultations and meetings with Jilly before Caruso finally orchestrated the opening of Jilly’s Rush Street Lounge in Chicago in 1981. Its meteoric success was sparked, in no small part, by the Sinatra influence. During the turbulent Eighties, social, political, and demographic changes began to impact the Street. Eventually, Rush Street succumbed to those changes. Jilly’s, along with other anchor tenants that had given the Street its glitter, was forced to close its doors. 

Like the perennial seasons, Rush Street once more reinvented itself. As we entered the 90s, the Gibsons and the Carmines began replacing the Sweetwaters and the Adolphs that were the Rush Street icons of the 70s and 80s. Reminiscent of a climax forest, the street awaited theCaruso/Sinatra ingredient to complete its resurrection and restore its lost glitter. 

Like the legendary Phoenix, Caruso’s Jilly’s responded. On May 6th, 1995, Jilly’s opened its doors once again on Rush Street. The Caruso/Sinatra rebirth was an overwhelming success. That success spurred the expansion of the Jilly’s Entertainment Group. By the end of the nineties, the Jilly enterprise, led by Nick Caruso, had opened a Jilly’s in Lake Geneva, Wisconsin. Prior to the untimely death of Jilly Rizzo, plans had been in place to open a 20,000 square foot Bistro lounge in Las Vegas. 

As we entered the new millennium, Jilly’s expanded eastward, to New York. In August 2001, the New York Jilly’s opened its doors. Before the successes portended by the gala opening could be realized, New York was hit by the now infamous September 11th terrorist attack. 

Shortly after, another crippling blow was dealt to New York’s food and beverage industry when an ordinance was passed banning smoking in public places. That combination proved devastating to the newly-opened Jilly’s Bistro. 

Caruso’s father, Sam, although living the last 35 years of his life blind, continued to excel at his trade and to provide for his family. Nick battles a similar set of problems, among them a diabetic condition that has significantly impaired his vision. Perhaps it is again the same genetic connection to the great Joe DiMaggio that enables the Carusos to take the blows and, through it all, manage their expectations. 

I share with you this excerpt from Ernest Hemingway’snovel, The Old Man and the Sea. I quote from memory:

The old man, struggling to fight off sharks eating away at the prize fish he caught and struggling to overcome the painful burns from the rope holding the great fish to the side of his boat, renews his will and summons the courage to endure by comparing his struggle with the struggles that faced Joe DiMaggio during his waning years. “His heel was so painful he could barely put on his shoe before each game. He did not give up, he did not complain, he did not make excuses.”

Not unlike his dad, Nick’s presence and his words continue to command the attention of business associates and personal friends. When visiting the Blue Boys’ Club at Polk and Aberdeen (as he occasionally does on Friday afternoons), Nick Caruso can be found at the center table reminiscing with his Taylor Street boyhood friends. When the language suddenly clears up, table by table and room by room, it is a signal that his wife, Pat, has arrived. Like the summer wind, Nick’s brief stay, prior to embarking on the return trip to his home in Oak Brook Terrace, fans the embers of memories and reveries of times gone by. It is a welcome glow. 

A quarter century spent in the inner circles of Frank Sinatra has brought Nick and his wife, Pat, in contact with numerous celebrities. In addition to the Lasordas and Randazzos, they included the Kennedy clan and an assortment of movie stars, TV personalities, sports figures, entertainers, and other celebrities—the noting of which would exceed the limitations of this writing. The guest list and congratulatory letters at his recent birthday celebration attest to the strength of those friendships as they endured through the years.

Nancy Sinatra remains close to the Caruso clan. Time will tell if Caruso will, once again, take on the treacherous cliffs and the unpredictable winds of the entertainment industry. If so, like the great ancestral navigators before him, the charts he has accumulated will inspire confidence in the crew assembled for the journey. And even if he decides to pursue a retirement away from new business endeavors, the territory he has already charted will serve as an inspiration to others. 


Nick Caruso, Sr., died in August of 2006, shortly after the above story was written. The media was granted permission to use segments of this article in their tribute to Nick Caruso.