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Golf great Phil Mickelson wasn't anywhere near a courthouse in California on Monday when a 57-year-old money launderer was sentenced to a year and a day in prison. The name of the three-time Masters winner didn't even come up.

But for the second time in less than a month, Mickelson's gambling was linked to court proceedings in which a suspected gambling associate faced criminal charges. Gregory Silveira, who was also fined $18,000, had pleaded guilty to money laundering for transferring $2.75 million between bank accounts in March 2010 for an unidentified client to promote an illegal gambling operation. Mickelson was the gambler, according to a man who describes himself as a longtime friend of Silveira's and two other people familiar with the matter.

In a different case three weeks ago, Mickelson agreed to pay back almost $1 million he earned by trading on a stock tip from friend and gambler William "Billy" Walters, according to the Securities and Exchange Commission. Walters, who faces charges of insider trading, has pleaded not guilty. Mickelson hasn't been accused of wrongdoing in either case.

Mickelson's ties to the two men threaten the image of one of the game's most popular players and forces the PGA Tour — which is considering allowing online casinos to host real-time gambling on its tournaments — to confront whether his betting puts the sport at risk. The code of conduct tells players not to associate with gamblers and others who "might reflect adversely upon the integrity of the game."

Therein lies a dilemma: Can the tour turn around and court gambling without attracting professional gamblers, or even criminals, who are drawn to big bettors like Mickelson?

"The slippery slope would be very slippery," said former PGA Tour player Joe Ogilvie, who was a member of the Tour's Player Advisory Council as well as the policy board during his playing career. "You do not want fringe groups that may not have the player's best interest at heart exerting pressure on the player by means we may not be aware of."

Officials at the PGA Tour won't say whether Mickelson violated the code or if they're investigating. Unlike other professional sports leagues, the tour's policy is to not to comment whether players are disciplined. A spokesman, Ty Votaw, wouldn't answer questions about Mickelson.

Representatives for Mickelson also declined to comment. Previously, Mickelson's attorney, Gregory Craig, said he was an "innocent bystander" to Walters' alleged trading scheme and that Mickelson would return his proceeds because he didn't want to benefit from a transaction the "S.E.C. sees as questionable."

In many ways, golf is a game made for wagering, with some of its greatest players learning the sport through the well-played hustle or pursuing friendly wagers during practice rounds. Until recently at least, Mickelson's wagers appeared to be mostly in good fun. He scored big on the Baltimore Ravens' Super Bowl win in 2001, telling reporters, "I also pick the NCAA tournament ... which was Duke, by the way."

Other bets didn't turn out so well. Near the end of 2015, Mickelson offered 17-year-old rising star Ryan Ruffels 2-to-1 odds on a $2,500 bet. The young Australian phenom told the Sydney Morning Herald that he birdied six of the last seven holes and beat Mickelson. A month later, a peeved Mickelson criticized Ruffels for divulging details of their bet, dismissing it as "high-school stuff."

Some of the golfer's bets have been far bigger. He lost almost $2.5 million at Las Vegas casinos from October 2000 to June 2003, according to the Wall Street Journal.

According to Silveira's court filings, the $2.75 million wire transfer from a gambling client was to cover "losing wagers." Silveira, who prosecutors say was involved in "illicit high-level sports betting," told the court his actions were a "misguided desire to help friends."

"Mr. Silveira, virtually as a personal favor to an individual who did not wish his wagering activity to become public, handled the payment of the funds," his lawyers wrote. "Silveira simply deposited his acquaintance's gambling loss payment into his own account and, thereafter, transferred it to the offshore sports books with whom the funds had been bet."

In court papers, Silveira said he "knew the gambler was involved in high-profile legitimate business."

Donald Foley, who says he has known Silveira for more than 20 years as a golf partner and friend, said in an interview that Silveira told him that Mickelson was the gambler in the money-laundering case. The other people who confirmed Mickelson's involvement asked not to be named because some details of the case aren't public. Mickelson was also previously identified as the gambler by ESPN when it reported on Silveira case's last year.

Neither Silveira, who lives in La Quinta, California, and San Diego, nor his attorney returned messages seeking comment on Mickelson or his case, and they declined to speak after the sentencing.

"I was a well-known sports handicapper for 25 years," Silveira told the court on Monday. "I'm the dumbest money launderer who ever lived."

Mickelson's ties to Walters and his alleged relationship with Silveira have surfaced at a time when golf's popularity has eroded. The number of participants has slowly declined to 25 million from 30 million a decade ago. Golf courses are closing at a rate of 150 a year. It may be a reason the PGA Tour has sought proposals from data companies to submit bids to package real-time tournament data into feeds for gambling houses. That idea opens the door to manipulation, tempting players to miss a putt or shank a drive, said Lia Nower, co-director of the Center for Gambling Studies at Rutgers University.

"It's kind of hypocrisy," said Nower, of the PGA Tour and other professional sports that have courted online betting. "You have these conglomerates that are invested in these legal gambling ventures, and they are turning around and telling their players that they can't gamble."

It may be too soon to know if Mickelson's alleged relationship to Silveira, coming just after his friend and gambling associate Walters' indictment, will undermine his popularity. His sponsors have stood by him. So, too, will his hardcore fans, said David Berri, a Southern Utah University economics professor and sports-branding expert. "To them he is a hero. We've seen it over and over. They just don't care."

Casual fans are not nearly as forgiving, and that could affect his endorsements since sponsors want to appeal to the broadest audience. "Anything associated with finance would have to think hard about having him endorse them," Berri said.