ANTHONY Martin Sinatra was a prizefighter. His ring name was Marty O’Brien because Italian boxers would use Irish names in the hope that it would endear them to a New York audience. Born in Sicily, he fought out of Hoboken in New Jersey having emigrated several years earlier. According to BoxRec, ‘O’Brien’ debuted in 1910 and wound up winning four and losing six while other records have him at 1-7. There were no listed fights between 1914 and 1920 but O’Brien came back and fought twice more, losing both and bowing out. It is likely that he met his wife, Dolly Garaventa, through another fighter as she was the sister of Dominick Garaventa. But Dominick was into other things besides boxing and was caught up in bootlegging, eventually getting arrested after a shooting incident. ‘O’Brien’ and Dolly were married in 1913 and two years later they had a son, calling him Francis Albert Sinatra. He would be known as Frank Sinatra.
With boxing in the blood and parents who owned a bar, young Sinatra had his share of scrapes. There was a scar above his nose and he’d picked up other damage, to his mouth and ear, later saying: “I was hit more times than a fender in a parking lot.”
He reckoned he got his first boxing gloves at the age of five and the passion never left him.
Frank would say early in his singing career, “My favourite exercise is boxing,” and he could be seen backstage, gloved up and punching heavy bags before he performed. He was a regular at the gyms, where he watched pros spar, and he even had some publicity shots in trunks and gloves. In the detailed Anthony Summers biography, Sinatra: The Life, Summers wrote, “It was even reported that he fought as a semipro in Hoboken clubs.”
Obviously there’s no such thing as semipro, but what he might have done is moved around with the gloves on in front of a crowd for a few dollars a time in smokers.
Regardless, plenty have made it clear that Sinatra wasn’t much of a fighter. He didn’t need to be. He was one of the great vocalists but his love for the sport and the respect he had for boxers always shone through.
He forged close relationships with Hall of Fame stars but always wanted to get closer to the action. He bought a stake in New York light-heavyweight and heavyweight contender Tami Mauriello – also known as The Bronx Barkeep – who fought Bruce Woodcock and challenged Gus Lesnevich (twice) and Joe Louis for their world titles. He also had a piece of another heavyweight, Chuck Crowell, who’d fought Buddy Baer and Lou Nova and he managed solid Chicago welterweight Ray Brown, who once went 10 rounds with the brilliant Ike Williams.
Sinatra even tried his hand at promoting, staging the 1947 clash between Jersey Joe Walcott and Joey Maxim. Walcott won with a dull split decision over 10 rounds in front of a crowd of 9,747 at Gilmore Field in Los Angeles. Cary Grant and Mickey Rooney were in the star-studded crowd, Joe Louis boxed a four-round exhibition in a show which was headlined, Will the three Joe’s ever meet? There were pictures of Maxim, Louis and Walcott on the fight poster and it said, “Frank Sinatra presents… for Hollywood Square Garden Inc… The Fight of the Year.”
It was anything but. Even Sinatra would concede that. “I was very disappointed,” Frank would say, “both in the fight and the turnout.”
But despite the downsides, his passion remained. In 1953 he was ringside at White City Stadium in England to watch Randolph Turpin outpoint Charlie Humez over 15 rounds. He had a genuine interest in boxers and a fondness for them. There was one story that he was staying in a hotel where one of the employees shining shoes was a former champion who’d fallen on hard times. As soon as Frank was told who it was, he gave him $1,000.
Sinatra also managed Los Angeles lightweight Cisco Andrade through the 1960s, Andrade was being trained by Al Silvani, who would become close with the singer. They had met in a New York bar years earlier and Sinatra wanted to learn some of the intricacies of the sport. “I took him to Stillman’s and taught him how to throw a punch and how to move,” Silvani said. “He caught on quickly.”
The two were firm friends and they’d travel together. Some saw Silvani has an assistant or his security detail but in the 1970s Silvani, who had bit parts in several Sinatra films, said: “I don’t like the word bodyguard. But if somebody starts to cause trouble, I can take charge.” This was notable because Sinatra had Mob ties so anyone charged with protecting Ol’ Blue Eyes had to be hugely respected.
Incidentally, Silvani’s decorated training career saw him work with Carmen Basilio, Henry Armstrong, Jake LaMotta and Eddie Machen, among many others.
In 1968, Sinatra starred in The Detective, based on Roderick Thorp’s novel, and there were roles for Sugar Ray Robinson and boxing writer George Plimpton. It was said that Sinatra was often part of Robinson’s ever-expanding entourage. Three years later came Sinatra’s most famous ringside experience.
Anybody who was anybody was in Madison Square Garden when Joe Frazier defeated Muhammad Ali in 1971’s Fight of the Century in New York. A-listers, pimps, gangsters… The guestlist was so extravagant only the cream of the crop was allowed in. Sinatra had a press seat and photographed the main event for LIFE magazine. One of his images even made the cover.
Like many at the time, however, Sinatra was not an Ali fan. He had been turned off by Ali’s self-confidence and draft refusal. He’d been ringside at the first fight between Ali [then Cassius Clay] and Sonny Liston, sitting next to Elizabeth Taylor and Jackie Gleason, but he would only come around to Ali years later. Ali’s former manager Gene Kilroy reflected on the night Ali met Frazier at The Garden in one of the biggest sporting events of all time.
And there was Sinatra, snapping pictures on the ring apron, the best seat in a packed house, camera in hand.
“Jilly [Rizzo] had a bar in New York called Jilly’s and they auctioned the pictures off and Sinatra signed them and they asked Ali and I to go there and Ali signed the pictures [too],” said Kilroy. “Sinatra liked Ali. He said he didn’t like him at first but everything Muhammad said he would do, Ali did.”
Kilroy was referring to Ali’s braggadocios nature, predicting the round of his opponent’s demise and so forth. It was something the establishment took time to warm to.
“Sinatra was a big Joe Louis fan,” Kilroy added. “He helped Joe many, many times and when Ali fought Larry Holmes in Caesars Palace, Sinatra was appearing there and he was sitting ringside about three rows back and I had a security guard move two chairs over and put them [Louis and Sinatra] right by the ring. Then, Sinatra said that night [after Holmes had beaten the ghost of Ali], ‘There’s a man in a room upstairs, he has nothing to be ashamed of. He’s truly a great man, he has a great heart and he’s a champion in and out of the ring’. That was the tribute Sinatra gave to Ali.”
Sinatra, who as an adolescent had the likes of Jack Dempsey and Gene Tunney to look up to, had seen many of the great heavyweights up close and personal. He was ringside for Rocky Marciano’s 1953 rematch win over Roland LaStarza, saw Ali, Frazier, Floyd Patterson, Liston and others but there was only one who was truly close to his heart and that was Joe Louis. As he wheeled a decrepit Louis into a room for a 1980 benefit evening for the fallen great at Caesars Palace, Sinatra said: “We’ve been friends for about 35 years. [From] the first time I ever saw him… I’ve been cheering him ever since. I think this is long overdue. God bless him. He’s going to have a good time tonight.”
After Louis suffered a stroke, Sinatra had the heavyweight legend flown in his private jet to Texas for the best treatment and rehabilitation money could buy. He told Joe’s wife, Martha, not to give the cost a second thought.
Then, when Louis died, Sinatra spoke at the funeral. “Joe’s biggest fight ended a few days ago,” lamented Sinatra. “And I don’t know how the refs voted yet, but I lay you 100 to 1 he gets a unanimous decision.”
With Joe gone, Sinatra’s passion for the fights remained, taking an interest in the wildly-popular heavyweight Gerry Cooney, who he did some publicity shots with before Cooney fought Larry Holmes, and Ray ‘Boom Boom’ Mancini. The Youngstown lightweight was big business in boxing and Sinatra wanted to see what the fuss was all about.
That the Chairman of the Board, as Sinatra was dubbed, took an interest in him blew a young and impressionable Mancini away. Mancini’s family were Italian immigrants, like Frank’s.
“I got to meet Mr Sinatra through mutual friends not long after I won the title and then when I defended my title in Vegas he said he was going to be there,” explained the former WBA champion. “I was training in Palm Springs and he said he was going to come and watch me train but then he couldn’t make it. So Jilly Rizzo, his right hand guy came, and Jilly told me ‘Mr Sinatra wanted to come but he couldn’t be here, he apologises but he’ll be at your fight in Vegas, he sends his love, his prayers and all that good stuff’. He didn’t have to apologise to me but he wanted to, so I was honoured. Then, of course, I saw him a couple of days before the fight backstage when he was rehearsing for a show, we had a photo, he invited me to the show after the fight, which I went to, and it was a wonderful moment.”
The fight Mancini was referring to had terrible consequences as his Korean opponent Deuk Koo Kim died from injuries sustained that night. “Mr Sinatra was great,” Mancini added. “He’d say to me, ‘Call me Frank’ but it was Mr Sinatra for me.”
After Mancini-Kim, Sinatra still couldn’t shake the boxing bug. Online, you can trace pictures of him hamming it up with dozens of boxing stars, including Esteban DeJesus and Vito Antufermo. He was ringside at the Marvin Hagler-Sugar Ray Leonard superfight in 1987.
It was said that Donald Trump, then helping promote the huge Mike Tyson-Michael Spinks bout in Atlantic City, was arranging the ring to be lower than it usually is so Sinatra wouldn’t have to crane his neck to watch. Frank didn’t even go. But he had been there a couple of fights earlier when Tyson blew away Larry Holmes.
By 1990, however, Sinatra’s health was beginning to falter. He toured in the UK and, recalling a show at Ibrox Stadium, his son Frank Jnr said, “His vision wasn’t what it had been. His hearing wasn’t. His memory wasn’t and he was struggling.”
Sinatra died in 1998.
It had been a goal to make it the millennium but his story was over, and so was his life in boxing.