The federal government was trying to pin an extortion and racketeering charge on Jackie "The Kid" Giacalone, a made man with an inalienable pedigree. Jimmy Hoffa had been on his way to a lunch meeting with Giacalone's uncle "Tony Jack" the day he was so permanently disappeared.
As a witness, prosecutors called "Dandy Don" DeSerrano, a bookie from Grosse Pointe who had been caught fixing poker games at an underground casino run by Giacalone and the "Detroit Partnership". During cross-examination, defence attorney Neil Fink sought to discredit any potentially incriminating DeSerrano evidence by bringing up his dealings with Phil Mickelson in the 1990s.
“Did you cheat him out of $500,000?” asked Fink.
“I wouldn’t say I cheated him,” said DeSeranno.
“What would you call it?” continued Fink. “What did you do?”
“I couldn’t pay him.”
That Mickelson was ripped off by a mobster is neither surprising or shocking and his pearl-clutching performance in Detroit was risible
Giacalone was acquitted and the transcript of the 2007 trial, replete with the strange cameo involving one of the world's best golfers, remained sealed for 14 years until the mafioso's most recent legal trouble brought it to the attention of Rob Snell, a Detroit News reporter.
Ahead of the current US PGA champion arriving in town for the Rocket Mortgage Classic on July 1st, Snell wrote the wonderfully-headlined “Lefty and the Dandy Don”, a piece detailing how Mickelson made sizable bets with a mobbed-up, local bookie. Such great newspaper work that the subject of the story threw a hissy fit about it and threatened to never darken the city’s door again.
“It was so much effort for me to be here and to have that kind of unnecessary attack... not that I care – it happened 20-something years ago – it’s just the lack of appreciation,” said Mickelson, not doing much for the prevailing view that elite golfers are supremely cossetted. “I don’t see me coming back. Not that I don’t love the people here, they have been great, but not with that type of thing happening.”
Pointedly, he didn’t deny a single thing from the report. How could he? More than two decades ago, Mickelson boasted about putting $20,000 on the Baltimore Ravens to win Super Bowl XXXV, a pre-season wager that yielded nearly half a million.
In a country where athletes betting on sports is frowned upon due to the lingering spectre of the 1919 Chicago Black Sox, he crowed so much about picking winners in the NFL that, for a time, he was even offering gridiron tips to punters on Dan Patrick’s national radio show. That he was ripped off by a mobster is neither surprising or shocking and his pearl-clutching performance in Detroit was risible.
Mickelson's entire career has been intertwined with gambling of every stripe. In 2012, he was $2 million in the hole to Billy Walters, a legendary figure around Las Vegas for his ability to take bets on sports and to pick stocks that only seemed to go up. To help his celebrity debtor out, the sometime Wall Street guru/regular subject of police investigations into illegal bookmaking passed him inside information about Dean Foods, a company set to announce excellent quarterly results and a possible lucrative spin-off.
Befitting a man who earned $45 million that year from winnings and endorsements, Mickelson invested nearly $2.5 million in shares, made a profit of just under $1 million inside a week, and then immediately paid that over to his friend cum bookie to halve the debt. Nice work if you can get it.
Part of his legend comes from locker-room lore surrounding on-course wagers he makes against fellow pros during practice rounds
When the Securities and Exchange Commission came sniffing around those transactions, Walters ended up getting five years in jail, the loose-lipped chairman of Dean Foods got a two-stretch, while Mickelson received a rap on the knuckles and a fine that was the exact amount of his profits. After his sentence was later commuted by president Trump, the White House claimed Walters’s most famous golfing pal beseeched the man in the Oval Office to issue the pardon. Mickelson’s attorney claimed he had nothing to do with it.
Of course, Walters isn't the only sketchy associate of Mickelson to find himself on the wrong side of the law. There have been other casualties too. In 2015, a former sports handicapper named Gregory Silveira of La Quinta, California, pled guilty to three counts of laundering $2.75 million from a "gambling client" listed in court documents as P.M and was sentenced to 12 months.
Silveira worked as an intermediary between the man who wanted to place wagers and an illegal offshore betting syndicate. ESPN’s investigative programme Outside the Lines confirmed with several sources the person transferring the money to him was Mickelson, who later dismissed the story as “a little report”.
With that sort of resume, it's astonishing the same man had the temerity to be offended by a newspaper documenting his historic travails with a delinquent bookie. Remember, Golf.com once did a lengthy and hugely entertaining feature called "10 Outrageous Phil Mickelson Gambling Stories" chronicling him betting on everything from audacious trick shots to professional boxing matches.
Part of his legend comes from locker-room lore surrounding on-course wagers he makes against fellow pros during practice rounds, so much part of the culture that losing money to him seems almost a rite of passage for unsuspecting, starstruck rookies.
The cash involved there might be trifling sums for rich men but it’s difficult to think of any other sport where one of its biggest stars being repeatedly entangled with illegal gambling and the mob wouldn’t and shouldn’t be a bigger deal.
