Rocco Caputo, beloved Wrigley Field vendor who appeared on ‘Undercover Boss,’ dies at 56

Rocco Caputo earned many loyal customers with his easy smile as a vendor at Wrigley Field for decades. His sister said his colleagues and customers were his family. (Provided)

Rocco Caputo put the “friendly” in The Friendly Confines of Wrigley Field.

As a vendor at the ballpark for 40 years, his easy smile and kind disposition brought a devoted crowd of regulars to his section behind home plate, many of whom would only get their beer from him.

“Many times I would walk down an aisle and people would just be yelling, ‘I’m waiting for Rocco, I’m waiting for Rocco,’” said David Levenson, who worked as a vendor alongside Mr. Caputo for decades.

“The fans really took to him, he was just a very personable guy,” Levenson said.

His legendary career garnered him a couple of memorable television appearances. In 2010 he supervised an incognito Cubs co-owner Todd Ricketts in an episode of TV’s “Undercover Boss.”

And in 2016, Mr. Caputo showed Stephen Colbert the proper way to sling hot dogs at Wrigley for a segment of “The Late Show With Stephen Colbert.”

“I don’t think anybody ever had a bad word to say about Rocco,” Levenson said.

Mr. Caputo died Tuesday of complications from liver transplant surgery, according to his family. He was 56.

As news of his death spread online, members of the tight-knit vendor community and former customers shared their stories and condolences on social media.

“Rocco was one of the nicest guys I have known,” wrote one person. “He loved the Cubs, he loved his customers and friends,” wrote another.

Christine Cutrone, Mr. Caputo’s sister, said season-ticket holders and Cubs players’ wives — whom he got to know because many sat in his section — have reached out to share their grief with the family.

“He was the most generous, the sweetest, kindest, greatest brother you could ever ask for,” said Cutrone, 60. “Whatever you need he would be there for you in a heartbeat.”

RIP #Cubs legendary beer vendor Rocco. pic.twitter.com/4CRgoUyZqc

— Danny Rockett (@SonRanto) December 27, 2023

Mr. Caputo was born Sept. 14, 1967. He and his siblings grew up in Old Town and later Bridgeport. The family moved to Oak Lawn as Mr. Caputo entered his teens. He attended Harold L. Richards High School.

He seemed destined to become a vendor. His father, Nicholas “Cappy” Caputo, was a longtime vendor at Wrigley and a union steward. Many members of his family have also worked at the ballpark.

Mr. Caputo followed in his father’s footsteps when he was 16, selling sodas and hot dogs as a vendor. He’s also worked at Comiskey Park, U.S. Cellular Field and the old Chicago Stadium. But Wrigley is where he spent most of his time.

Rocco Caputo threw out the first pitch at a Cubs game in 2010. (Provided)

Tony Castro, a close friend and vendor who worked with Mr. Caputo for 25 years, said that at work they would affectionately call Caputo “the Penguino” because he sounded like a penguin when he’d talk for a long stretch.

“I’m going to miss his smile,” he said.

Castro, 61, said Mr. Caputo was a foodie, who knew where the best Italian beef or Italian sausage spots were in the city. He became a bit of a celebrity after his “Undercover Boss” appearance, Castro said.

“He would sign autographs for little kids, bring his own baseballs and sign them and give them out when people would ask,” Castro said.

In the “Undercover Boss” episode, Caputo becomes irked with Ricketts for throwing out some hot dogs. Ricketts had apparently bought them himself after failing to sell them in the stands.

Ricketts tells Caputo that seeing his work ethic inspired him to create the Wrigley Field Award and named Caputo the first recipient. Mr. Caputo threw out the first pitch at a Cubs home game after the episode aired.

“He was a sweetheart as a person, he was just nice to everybody,” said Rich Harris, a former Sun-Times editorial assistant and vendor who knew Mr. Caputo for decades.

Rocco Caputo sporting the smile that made him a beloved fixture at Wrigley Field. (Provided)

Harris also remembered Mr. Caputo’s indelible smile.

“When you would be worried about something, or just pointing something out, if there was a problem, he’d say, ‘It’s all good!’ with that smile,” Harris said.

Mr. Caputo didn’t marry or have children, but his sister said the people he surrounded himself with were more than enough for him.

“He was married to that vending life,” Cutrone said. “His family was the vendors, his family was the fans.”

Services for Mr. Caputo will be held at Blake-Lamb Funeral Home in Oak Lawn on Jan. 2.