Sport: Golf
Career: 1996-Present
Cockiest Quote: "I want to be what I've always wanted to be: dominant."

The confidence of Tiger Woods would intimidate every fifty-something "athlete" in a pair of pleaded khakis on the links. For years he was the most dominant golfer in history, scaring the mashed bananas out of every geriatric on the PGA Tour. But his golf game was nothing compared to his side hustle. The "cockiest" golfer of all blatantly cheated on his wife with a seemingly endless list of porn stars and reality TV castoffs. He's kind of lost his "eye of the tiger" since the whole saga played out publicly, but if dude gets his swag back, lock up your daughter and invest in green jackets.