President Barack Obama talks with professional golfer Tiger Woods in the Oval Office of the White House, April 20, 2009, in Washington. Image Credit: Pete Souza / The White House / Getty Images

President Obama's decision to golf this past weekend with Tiger Woods, one of the most unpopular athletes in the country, was understandable for a golf fan but was a gamble for a president, one commentator said today.

Obama, who is vacationing in Florida, teamed up with Woods Sunday at a posh resort, The Floridian in Palm City, Fla., far away from cameras and reporters who were kept from covering the president's activities over the weekend. Obama also received private golf lessons Saturday from Woods' former coach Butch Harmon and his son.

The White House and a spokesman for Woods have declined to comment about Sunday's game.

In partnering with Woods, the president not only picked one of the best golfers ever, but one who was notorious as a serial philanderer. In November 2009, reports emerged about Woods', who was married to model Elin Nordegren at the time, extramarital affairs with dozens of women, causing the athlete to take a break from golf and receive treatment for sex addiction.

Earlier this month, Forbes released its list of the top 10 least liked athletes in the country. Woods ranked as the third least liked athlete in the U.S. with a 19 percent appeal rating after cyclist Lance Armstrong and Notre Dame football star Manti Te'o.

"Tiger Woods is one of the greatest golfers to ever live, so I can understand why someone who enjoys golf would want to play golf with one of the greatest golfers to ever play the game," said Christine Brennan, a sports columnist for USA Today and sports consultant for ABC News.

"When you consider that Tiger Woods is in the top 10 of the least liked athletes on earth and when you consider that no mainstream sponsor other than Nike wants to touch him, I would say that the president gambled a bit on this one," Brennan said.

While the weekend game was their first match up on the golf course, Obama briefly met with Woods at the White House in April 2009, months before the golf star's infidelities came to light.

Woods has worked to reboot his image after the divorce from his wife and the loss of numerous endorsement deals. Woods returned to golf in April 2010 but has struggled to regain the success he achieved in his early years.

Regardless of the scandal which engulfed Woods' professional and personal life, Obama consistently expressed confidence in Woods' ability to rehabilitate his image.

"I don't want to comment on his personal relationship with his wife and family, but I'm a strong believer that anybody can look within themselves, find their flaws and fix them," Obama said in an interview with People Magazine in January 2010.

Months later, Obama predicted Woods would still be successful in golf.

"I think that Tiger has acknowledged that he betrayed his family and that's a personal issue that he's got to work out," Obama said in an interview with Fox News in March 2010. "I hope they've worked it out. I'm sure he's going to still be a terrific golfer."

Tim Rosaforte, a senior writer for Golf World and Golf Digest reported on the Golf Channel Sunday that the president told Woods how happy he was to see him win the Farmers Insurance Open earlier this year.

The president and Woods, who were teamed up against U.S. Trade Representative Ron Kirk and Houston Astros owner Jim Crane, who owns the resort, played 18 holes in just over four hours and won $15 from their opponents, Rosaforte reported.

"Both of them left happy…because they both got a 'W' out of it and you know how important 'W's are for the president and for Tiger Woods," Rosaforte told the Golf Channel Sunday.

The president played an additional nine holes of golf on his own after Tiger left, Rosaforte said.

Rosaforte is the only known journalist to have seen the president this weekend, after the resort was locked down to the traveling press. Rosaforte's access was reportedly influenced by his membership to the exclusive golf and yacht club. In a phone interview with MSNBC, the sports commentator said he briefly spoke with the president during his visit.

"It's harder to find a man that's happier than the president was coming out of there yesterday after getting tweaked by the Harmons," he said.

Woods will play at the World Golf Championships-Accenture Match Play in Marana, Ariz. on Wednesday and is seeded number 1 in his bracket. Woods has won the event three times, but he has not advanced past the second round since his 2008 win.

Throughout his presidency, Obama has hit the golf course while on vacation and on the weekends in the Washington, D.C. area. The president has said golf helps him feel like he's "outside" of the bubble of the White House.

"It is the only time that for six hours. First of all that I'm outside," Obama told CBS News in 2009. "And second of all, where you almost feel normal. In the sense that you're not in a bubble. There are a whole bunch of Secret Service guys, but they're sort of in the woods."

"It's as- as close as you're going to get to being outside of this place," Obama added.

The president often golfs with friends and donors. Crane, who played against him this weekend in Florida, held a fundraising event for the president in 2012 at Minute Maid Park, the stadium where the Houston Astros play. The event was one of two fundraisers that evening which raised a totally of $2.7 million, the campaign said at the time.

Obama has teed off with other politicians, including House Speaker John Boehner, R-OH, and former president Bill Clinton, but he also recently had a golf outing with his longtime friend, Bobby Titcomb, who was arrested last year on suspicion of soliciting a prostitute.

The president has also gone head to head with another professional athlete on the basketball court. On Election Day, he played with former Chicago Bulls player Scottie Pippen in his traditional pre-election game.