Pete Caldera Sings Frank Sinatra: How a Sportswriter Channels the Chairman of the Board

The New York Yankees had just suffered one of the more bizarre postseason losses in the Joe Torre era, a 2-1 defeat in the second game of the 2007 American League Division Series against the then-Cleveland Indians. That was the game in which Lake Erie midges made a cameo appearance and created havoc, especially for Yankees reliever Joba Chamberlain.

In the funereal atmosphere of the visiting clubhouse at Jacobs Field, the New York reporters assembled in front of Alex Rodriguez’s locker, waiting for the third baseman to address the team’s loss and the 0-2 hole the Yankees were in heading back to the Bronx. Pete Caldera, the beat writer for the Bergen Record, started to take his place in the media maw, but not before Hall of Famer Reggie Jackson made eye contact with him.

“It doesn’t look good, Frank,” Jackson whispered to Caldera.

“And to this day, there are times I’ve called [Jackson] on the phone and I had to tell him it’s ‘Frank,’ because I don’t think he knows my real name,” Caldera, 57, said in a recent interview. 

But Mr. October’s misidentification of Caldera is actually high praise, and alludes to Caldera’s moonlighting gig, one that’s officially almost two decades old. In that role, the sportswriter trades in his seat in baseball stadium press boxes for a tuxedo and a stage, and belts out the dulcet sounds of Ol’ Blue Eyes — Frank Sinatra. 

Officially, since 2006, Manhattan’s venerable Carnegie Club is where Caldera most often has performed Sinatra’s song catalog, to rave reviews, in front of the famed Stan Rubin Orchestra. Unofficially, Caldera has channeled the Chairman of the Board since his teenage days, growing up in Rockland County, when he would dig into his mother’s Sinatra record collection, or listen to Sid Mark’s The Sounds of Sinatra radio show. Caldera would sing along to Sinatra cassette tapes (remember those?) in the car, and he later attended over a dozen live Sinatra concerts. But it wasn’t until after the legendary singer and actor’s death, in 1998, that Caldera tried his hand at lounge singing.

None other than former New York Mets manager Bobby Valentine was responsible for one of Caldera’s earliest gigs.

“One night in San Francisco, on Bobby’s birthday, I was having a drink in the lounge at the St. Francis Hotel with Bobby and [fellow sportswriter] Larry Rocca, and we decided to go across the street to Lefty O’Doul’s,” said Caldera, referring to the legendary saloon named after the major leaguer who played for the Yankees, New York Giants and Brooklyn in the 1920s and 1930s. “I think Larry mentioned, ‘Pete sings.’ So Bobby throws $50 in the piano player’s tip jar, and says, ‘Let him sing anything he wants.’”

At the time, Caldera was covering the Mets for the Bergen Record, and the performance impressed Valentine so much that the manager later made a memorable introduction for Caldera in Chicago.

“As soon as I heard him, I thought he needed to sing at Jilly’s,” said Valentine. 

Jilly’s, as in the famous Windy City club run by Willy Rizzo, son of Jilly Rizzo. The same Jilly who was Sinatra’s best friend, confidant, bodyguard et al. Valentine introduced Caldera and Rizzo at Wrigley Field, and soon enough, Caldera was belting out “Chicago, Chicago, that toddlin' town …” in the landmark gin joint every time the Mets, and later the Yankees, came to town. Caldera said he remains close friends with Willy to this day. 

The roots of Caldera’s Sinatra appreciation began years earlier; his mom, Eileen, was the Sinatra fan in the family. Tony, the family patriarch, was, in Caldera’s words, more of “an opera, Elvis Presley-doo-wop” aficionado. 

“My mom had all the Sinatra albums. She had a huge collection, so I had those at my disposal,” said Caldera, who is one of three sons. “Then I’d start going to record stores and buying the cassette tapes of all those albums, to have them in the car. I built on the Sinatra library that my mom had.”

While most of Caldera’s teenage peers and friends were listening to the rock gods of that era, like Springsteen, the Stones, the Clash and U2, Caldera favored the swing and Hollywood golden era of music — Sinatra and Martin, Bobby Darin and Mel Tormé, and the great songwriters George and Ira Gershwin and Cole Porter.

“I was actually, what a shock, not the most popular guy in middle school or high school,” joked Caldera. “I was probably a little withdrawn, in my own world, which consisted of a lot of baseball and a lot of Frank. I had a lot of friends, but I wasn’t really outgoing.”

Caldera said he remembers going to New York's Belmont racetrack during his teens with his grandfather, who liked to wager on horses. One afternoon, the young Caldera spotted an “immaculately dressed” gentleman in a suit and green hat. Someone from the other side of the room at Belmont yelled out to the stylish gentleman, “Hey, Cabby, who do you like in this race?”

“I turn to my grandfather and ask, ‘Is that Cab Calloway?’ My grandfather says, ‘Yeah, he’s here all the time.’ I mean, that’s Cab Calloway! It could have been Joe from Flatbush. That floored me.”

Caldera saw his first Sinatra concert at Carnegie Hall in September 1985, when he was still a Hofstra student. He dragged one of his best friends from elementary school, Stu Rushfield, into Manhattan, and Caldera said that while he didn’t don a tux, he definitely was dressed for the occasion. Frank didn’t disappoint.

“That concert was phenomenal. I had tickets in the Dress Circle, just below the Balcony,” said Caldera. “I believe Pete Barbutti was the opening act. Sinatra came on without an introduction. He just walked onto the stage, and the applause sort of built as he walked the length of the stage, from stage right to stage left, towards where the piano was. He had the charts under his arm. He put the music on the piano, and went to the microphone and the first song he sang was, Come Fly with Me. One of his great openers. Never forget it.”

During the concert, Sinatra razzed the New York Mets fans, since the Los Angeles Dodgers were in town to play the pennant-chasing Queens ballclub. Sinatra also joked between songs that he and the state of New Jersey were at peace after a yearlong feud that reportedly involved a kerfuffle at the Golden Nugget blackjack table. 

“Frank and Dean Martin told the dealer to deal out of his hand rather than the [card] shoe, because they were Frank and Dean. I guess the dealer got fired and they came under scrutiny for running afoul of New Jersey [gambling laws],” said Caldera. “It caused a huge uproar. Sinatra carried out a threat not to play Atlantic City for over a year. At the [Carnegie Hall] concert, during his monologue, Frank mentioned that he and the state of New Jersey were now back on speaking terms. That was Frank.” 

Caldera said he even saw Sinatra after the performance, on West 56th St., waiting for his car. 

That was the first of about 14 Sinatra shows that Caldera attended. He also took his mom to a Radio City Music Hall Sinatra concert around 1990. But Caldera’s parents had seen Sinatra before, in the mid-’70s, at the long-shuttered Westchester Premier Theater, a venue that had its own colorful Sinatra history. 

“It turned out to be a mob-operated place that was skimming profits off the top,” said Caldera. “There’s a famous picture that Sinatra took backstage with just about every member of every crime family in New York at the time.”

After Hofstra, Caldera embarked on his sports writing career, with stops at The Middletown Record (aka the Times-Herald Record) and The Journal News. He covered Yankees and Mets home games in the late ’90s, and he was at the old Yankee Stadium for a game against the Texas Rangers on May 14, 1998. It was a date notable for a rare Yankee loss during what would be an historic season that culminated with a World Series championship; the Seinfeld series finale; and the death of Sinatra at 82.

“My old college roommate wakes me up about 6 a.m. the next morning,” said Caldera. “He said, ‘Hey did you see the news?’ ‘No, I’m asleep. What news?’ ‘Sinatra died.’ That’s how I found out.”

Once Caldera was on the Mets beat, and later as the Yankees beat writer, whenever he's been in Tampa during spring training, he hangs out with other writers at Donatello, the Italian restaurant/piano bar staple on Dale Mabry Highway. Donatello became Caldera’s training ground to perform live, and he still sings the hits there with Miss Kitty Daniels on the piano. Daniels is a jazz legend in her own right, and even has a documentary of her life, Kitty Daniels and Majid Shabazz Jazz Legends.

Everyone from Torre to Jackson to Hideki Matsui, even the late Grammy, Oscar and Pulitzer Prize-winning composer Marvin Hamlisch has caught Caldera behind the microphone at Donatello. The Hamlisch intro came through Torre, and later when the former Yankees manager and Hamlisch were dining at Donatello, Caldera had a surprise audience member.

“At least Marvin Hamlisch got to hear me sing one song,” said Caldera. “He was very complimentary and a very nice man. I think I impressed him because [I knew] he played piano for Groucho Marx when he did his one-man show.” 

Caldera would often pepper Torre with Sinatra questions when Torre was the Yankees skipper, and one anecdote still makes Caldera laugh.

“Torre told me about being invited to an Oscar party at Sinatra’s house,” said Caldera. “Frank’s Oscar for From Here to Eternity was in the center of the table and around it was the dip tray. Imagine dipping your Triscuit in the onion dip and you’re inches away from Sinatra’s Oscar. I enjoyed that one.” 

In 2006, Caldera hit the big time on the singing circuit, when he met the inimitable Stan Rubin. The orchestra leader chose Caldera to perform with the band, and their Carnegie Club shows have remained a hot ticket, almost 20 years later. Caldera said the key to the appeal is not trying to pretend you’re the Chairman of the Board.

“You can’t replicate Sinatra. You can only pay homage and respect to his musicality,” said Caldera. “Sinatra was all about the music. If you don’t have respect for the lyrics and the melody and the meaning behind it, you’re not going to have much of a show.”

In the late 2000s, Caldera started taking voice lessons with the renowned voice coach John Mace. The lessons were courtesy of Caldera’s wife, Jeannine, and Caldera would travel to the Upper West Side apartment of Mace and his partner, Richard Dorr, to further hone his singing chops. Mace worked with a who’s who of Hollywood icons, including Bette Midler, Morgan Freeman and Vanessa Redgrave. Mace died in 2017 at 97. 

“Richard Dorr was a lovely man, too, and a huge Red Sox fan,” said Caldera. “We would talk baseball after lessons.”

Caldera has branched out on his own, too, and recently performed his holiday show at the Milford (Pa.) Theater for the third consecutive year, although with a different set of musicians behind him. 

When he performed in Milford December 2, Caldera — like Sinatra did — joked with the crowd between numbers. Before the show, he said he hoped any Juan Soto trade to the Yankees wouldn’t occur until after his performance concluded. In the ever-evolving world of media, and newsroom contractions, Caldera said he’s happy — and lucky — to still be doing what he’s doing, and having a side hustle to boot. 

That singing chapter may very well take full swing down the road, if Caldera hangs up his reporting spikes.

“I love what I do as a writer. I’ve gotten to go places, cover many events. That was my dream as a kid,” said Caldera. “Would I like to do more music? Sure. Let’s do London, Paris, Rome, take it on tour some day. I’m all for anywhere the music takes me. Let’s hope my voice holds out that long.”