There was the devastation at the PGA Championship in 1996. Disaster at the Masters in 2009. Disappointment at the Senior PGA last month.
If there was a way to lose a major tournament, the affable 52-year-old Kentuckian seemed to have found it during his otherwise sterling career.
"I thought I was snakebit," Perry said. "I got close so many times and I just seemed to mess up down the homestretch and not make it happen."
This time, Perry didn't leave anything to chance.
After tap-in birdies at Nos. 16 and 17 gave him a two-shot lead over
"My word was patience," Perry said. "I wasn't going to put any pressure on myself to win the golf tournament because I had so much heartache, so many losses. ... I was just thinking `You know what, I'm tired of worrying about that.'"
Instead of feeling the pressure, Perry exerted it. He withstood an early charge from Waldorf, who birdied his first four holes, then kept firing at pins on the back nine while Couples' putter failed him.
The Hall of Famer leads the Champions Tour in putting average but could generate little magic Sunday. He drove the green on the short par-4 seventh only to three-putt for par. Couples later knocked it within 8 feet on the 15th only to send his birdie attempt streaking past the hole. He pulled the comebacker to the left and the bogey gave Perry his opening.
Perry stuffed a pitching wedge within inches on the 16th then hit a 6-iron to within 2 feet on the par-3 17th. He tapped in the birdie to maintain his two-stroke lead then played smartly on the 18th. He left it just short of the green in two and watched as Waldorf and Couples both reached the long par-5. Their long eagle attempts never sniffed the cup, and when Perry rolled in his par putt, he thrust the ball in the air just before the sky opened for one last deluge on the water-logged course.
Fox Chapel took on more than 4 inches of rain during the week, turning what was supposed to be a stiff test into a pitch and putt for long hitters like Couples and Perry. The conditions begged for players to attack the pins. Rather than simply protect par as he did during his near-misses in earlier majors, Perry knew he could go for it.
It paid off with a $405,000 check and one very significant weight off his shoulders.
"I'm hoping the floodgates are going to open," Perry said. "But I don't know, anytime you get into contention you get nervous, you get antsy. But today I had a peace about me ... if I can kind of draw upon this the next time I get into the heat of things hopefully I'll finish it off like I did today."
Couples was hoping to polish off his third major victory on the Champions Tour, but after cruising through the first three rounds he couldn't match Perry's shotmaking on the final day. Couples now has four runner-up finishes this season, including each of the last two majors.
"There were a couple shots you always should have back," Couples said. "The putt on  looked so easy and I just hammered it and I kind of flinched at it coming down the hill ... it was a little bit of a sour day the way I played after I teed off."
Perry trailed by as many as eight shots earlier in the tournament before tracking down Couples over the weekend. He drew within two thanks to consecutive 63s in the second and third rounds and kept it going Sunday.
It was sweet vindication for a player who has won more than $31 million during his 31-year career but is better known for those rounds that went all wrong.
The agony grew exponentially 13 years later, when he stood on the 17th tee at Augusta with a two-shot lead. Consecutive bogeys dropped Perry into a three-way tie with Angel Cabrera and Chad Campbell. He failed to get up and down on No. 10, the second playoff hole, and Cabrera made par to capture the green jacket.
Perry had another close call at the Senior PGA in May. He led through three rounds at Bellerive in St. Louis but was dogged by knee pain and overtaken by unheralded Kohki Idoki.
On Sunday, there would be no folding.
Buoyed by a hot putter, Perry teamed with Waldorf to wear down Couples.
Waldorf began the day four strokes behind Couples but wasted little time making up ground. He rattled off four straight birdies to start his round and shot 29 on the front nine. He cooled off after making the turn and finished with a 6-under 64, giving Perry enough room to pull away.
"It's not surprising, [Perry] is obviously a great player," Waldorf said. "Winning these majors isn't easy and he did a great job this week."