He won four times in 17 years, occasionally challenged in the majors, made enough money to easily keep his card and sometimes got into the Tour Championship for finishing in the top 30 on the money list.
Perry had no reason to believe this year would be any different, especially when he missed the cut at the Byron Nelson Classic. In fact, he booked a flight home in advance on Friday during the Colonial.
That's when it all turned around.
He not only made the cut at Colonial, Perry shot a career-low 61 in the third round and won by six strokes. He won twice more, part of an amazing run in which Perry hasn't finished worse than eighth in his last seven events.
'It's hard to explain why after 17 years of pushing, pushing, pushing, why all of a sudden am I pushing the right buttons this year?' Perry said. 'I just keep saying it's my time.'
Maybe that time is the 40s, an age that once was considered no man's land in golf -- somewhere between a player's prime and eligibility for Champions Tour.
Perry, 42, isn't alone.
Heading into the PGA Championship, he is among six players 40-and-older who have won on the PGA Tour, compared to only four players in their 20s who have won this year.
That includes 50-year-old Craig Stadler, who won the Senior Players Championship one week and the B.C. Open the next. It also includes Peter Jacobsen, 49, whose victory in the Greater Hartford Open gave him a two-year exemption and a difficult decision next year -- play against the old guys or the flat bellies?
'It's a nice problem to have,' Jacobsen said.
Players winning in their 40s is nothing new.
Sam Snead won 17 times after turning 40 and is the oldest PGA Tour winner -- 52 when he won the 1965 Greater Greensboro Open. Julius Boros won two majors in his 40s, including the 1968 PGA Championship at 48, the oldest player to win a major.
It seems to be happening with regularity, though.
Jay Haas is having one of his best years at 49, spurred on my better equipment and two sons in college, one of whom played with him in the U.S. Open.
Fred Funk, 47, tied for fourth in the PGA Championship last year and has showed no signs of age. He is among seven players in their 40s who are in the top 25 on the money list.
Haas thinks it's merely coincidence, the same way he explains a record 18 first-time winners on tour last year.
Still, he doesn't discount better equipment that allows the older guys to keep up, better fitness with the lucrative Champions Tour awaiting and the incentive of playing for 10 times more money than when they started.
They also have plenty of examples that it can be done.
'I think if you can point to one thing, you see some of your peers playing well and you think, 'Heck, I can play like Kenny Perry, Craig Stadler or Jay Haas,'' Haas said.
Rocco Mediate has the most simple explanation.
'We're good,' he said. 'We know how to play. We've been around. Because we're older doesn't mean we don't know how to win. That's happening this year.'
The next step is to do it in the majors.
The late Payne Stewart was the last player from the 40-and-older crew to win a major. He was 42 when he beat Phil Mickelson in the 1999 U.S. Open at Pinehurst No. 2
A year before, Mark O'Meara became the oldest player (41) to win two majors in one year. The previous record was Ben Hogan, who was 40 when he won all three majors he played in 1953.
O'Meara said it best in 1998 when asked what a man his age was doing with a green jacket and a silver claret jug.
'The golf ball is sitting out there on the ground. It really doesn't know how old you are,' O'Meara said. 'It just sits there, waiting to be struck. That's what makes this game so special.'
The ball still hasn't figured it out.
Tom Watson, 53 and an eight-time major champion, was tied for the lead after the first round of the U.S. Open and had another strong start at the British Open.
Vijay Singh turned 40 in April and has been a factor on the weekend at all three majors. Perry tied for third at the U.S. Open and was only two behind going into the final round at Royal St. George's, finishing in a tie for eighth.
Most eyes are on Perry heading into Oak Hill -- not because he is 42 and ready to send his second daughter to college, but because he is playing better than anyone right now.
'Everything is set up good for me,' Perry said. 'A lot of things have to happen your way to win a golf tournament. But I think I'll be very competitive, and I'll be right there at the end.'
Along with winning a major, Perry still has hopes of winning the money title and being voted PGA Tour player of the year, goals that seem more appropriate for someone much younger.
'At my age, 42, 17 years out there on the tour, never ever being close, now to even be considered for it -- it's been pretty neat for me to think about,' he said.
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