Had His Phil: Golfing Legend Mickelson’s Big Money Betting Exploits

Phil MickelsonHe’s the six-time major winner that did the unthinkable: winning the PGA Championship this year after turning 50.

Phil Mickelson’s exploits on the golf course are one thing, but the tales about his involvement in a betting ring – and various big money gambles he has placed over the years – are the stuff of legend in themselves.

Lefty, as he is known, is looking to add the Open Championship to his title collection this week, and you hope he is in a better mood than when he visited Detroit for the Rocket Mortgage Classic a few weeks ago.

There, the Detroit News timed a story to coincide with that tournament that claimed that Mickelson was swindled out of $500,000 by an illegal mob-lined bookmaker. So incensed was the 51-year-old that he vowed never to return to Detroit again.

And so it seems timely to look at the colourful betting career of the ever-popular left hander….

Crafty Jack and Dandy Don

The story that the Detroit News was referring to was the trial of Jack Giacalone and ‘Dandy’ Don DeSeranno.

Giacalone, the newspaper alleged, was an ‘organised crime leader’ in the city who would later face trial for racketeering and unpaid taxes in 2007, and Mickelson’s name appears in the federal court papers due to his involvement with a bookmaker’s assistant, DeSeranno.

He, it has been claimed, took a significant bet from a betting pool that Mickelson was involved in – when that subsequently won, it was reported that DeSeranno couldn’t find the $500,000 required to pay the PGA TOUR pro in winnings.

The story has been confirmed as true by Mickelson, however he was irked that the Detroit News dredged up an incident which took place 20 years ago as he took to the tee at the Rocket Mortgage Classic – he labelled the paper ‘opportunistic, selfish and irresponsible.’

This was just one of the tales that, while not that well documented, confirm the size and scale of Mickelson’s wagering habits.

Head’s Up

The 55-time winner worldwide is known for his penchant for making practice rounds a little more interesting.

And so it’s not unusual for Mickelson to bet against his fellow players when taking to the tee.

That was a scenario that 17-year-old Ryan Ruffels found himself in when he accepted an invitation to hit with Mickelson in Arizona.

Ruffels recalled a story to the Sydney Morning Herald that Mickelson gave him odds of 2/1 that he couldn’t beat his veteran playing partner – Mickelson would pay the Aussie $5,000 if he could beat him, and would invoice Ruffels for $2,500 when he turned professional.

The terms were agreed, hands were shook….and Ruffels went on to win the contest.

Mickelson happily paid up….although he was was less enamoured with the rookie for detailing their wager in print. “You don’t discuss certain things….he’s going to have to stop doing that now he’s on the PGA TOUR.”

Then there was the story that, during the Covid lockdown of 2020, Mickelson and fellow pro Xander Schauffele were able to get out on the course for some practice. Phil being Phil, he wanted to make it interesting – he went on to lose three rounds in a row to Schauffele, and forked out an ‘undisclosed’ sum for the privilege.

Walking on Walters

Billy Walters was a successful businessman and investor.

Quite how he came to befriend Mickelson is anybody’s guess, but it later came to pass that Walters had given Phil, let’s say, some investment ‘ideas’ that he might want to follow through.

In 2017, Walters was convicted of insider trading and various fraud charges, and he was sentenced to five years in prison – a sentence later quashed when his chum, Donald Trump, became the US president.

Unaware of the fraudulent activity, Mickelson invested in a number of the stocks suggested to him by the scam artist, and was named by the Securities and Exchange Commission in their investigation. He was made to repay $1.9 million, although he was not charged with criminal activity as he did not know of Walters’ connections.

Apparently the pair had become friends on the golf course, playing numerous times together in California and Nevada. In one such round back in 2012, Walters is alleged to have told Mickelson about a dairy farm that he believed was a smart investment – papers from the prosecution in the criminal case revealed the left-hander made nearly $1 million when selling the shares just one week later.

Walters is also known to be one of America’s most prolific sports bettors….perhaps that’s why and Mickelson get along so well.