The big-hitting left-hander from Bagdad, Florida, might appear to have it all -- two Masters green jackets and more than $30 million in winnings alone -- but he could be a couple of victories away from quitting golf.
After winning Tiger Woods' Hero World Challenge in the Bahamas Sunday, Watson suggested that he will retire if he ever becomes world No. 1.
It's not the first time he has floated the idea of packing it all in.
The 37-year-old, who is ranked fourth in the world, has previously claimed that he would quit when he got to 10 PGA Tour titles, but he told reporters in Albany that Woods' invitational event -- his ninth win - did not count as it was not officially sanctioned.
"Ten U.S. victories," a smiling Watson countered in his victory news conference. "I don't count this as a PGA Tour victory. It counts as a victory. It's very big for my career personally, but I don't see it as 10 ... I still need two more.
"But I will give you this, though. If I ever become No. 1 in the world, I'm walking away. I'm going to walk away on top. But let's be honest, nobody here's voting on that, right? Everybody thinks I'm not going to do that."
But don't bet against it.
Watson reached a career-high second in the world rankings in February, and a decent start to 2016 could see him eat into Jordan Spieth's lead at the top.
That could set up the tantalizing prospect of a career-defining clash with the defending champion at Augusta in April.
A third Masters title, on a track almost tailor-made for his length, right-to-left shot shape and creativity, could just be enough to take Watson to the top.
That would leave him just one green jacket behind Woods and Arnold Palmer, and three adrift of Masters pacesetter Jack Nicklaus.
Would you still retire?