Not quite 15 years later, he's shaking hands with royalty behind the 11th green at Royal Troon and leading the British Open.
'Can you imagine those people driving by on the street looking at me?' Kendall recalled. 'Black pants, white button-down shirt with a bow tie, hitting balls.'
A year after Ben Curtis shocked the golf world by winning the game's oldest championship, another relatively unknown American is in position to steal the Open. Yet their stories are very different.
Curtis was 26 last year and playing his first season on the PGA Tour. Kendall turns 40 in two months, he has already played in 310 tour events and his next victory will be his first.
'I really feel like I've been very close. I've lost in a bunch of playoffs. I really feel like I can win out on the PGA Tour as well as anyplace else. I think it's just a matter of time.
'Hopefully,' he said, 'this is mine.'
Whether or not it turns out that way, Friday was definitely Kendall's day. He holed out from a bunker at No. 3 to kickstart his round, then offset his lone bogey at the 11th with three more birdies and an eagle at the 16th by rolling in a 50-foot putt from just off the green.
Moments after signing his scorecard for a 66 that left him at 7 under - one shot ahead of Frenchman Thomas Levet - Kendall took his seat behind a table on a stage in the interview room. According to one of the more informal traditions that have sprung up at the Open over the years, the winner autographs that same table at the end of his session Sunday.
'I know that there's a long way to go and that this is only halfway done. But hopefully,' Kendall said, exercising caution once more, 'I'll be signing my name right here in a couple of days.'
A pen might be as sharp an object as he should be entrusted with at the moment. At the Memorial Tournament last year, Kendall tried to cut a frozen bagel before dropping it into a toaster and nearly sliced off his left forefinger.
'I didn't cut it completely off, but I cut a big piece of it off,' he chuckled. 'They had to sew it back on and I didn't play for, I guess, about four weeks.'
Because Kendall is one of those guys who has to play every chance he gets to hold onto his tour card, he devised a new grip in time to play last year's Open. To get into this year's tournament, Kendall played in one of four special 36-hole tournaments staged by the Royal & Ancient Golf Club around the world to give tour players a chance to qualify without having to travel to Britain.
'It was a no-brainer for me. Anytime I can try to get into a major championship, I'm going to be there,' he said. 'These are important to me - not only to test yourself, but to try and win one. And the only way you can do that is to try to get in.'
Never mind that 52 of his fellow PGA Tour players didn't even bother to show up for the qualifier. This is only Kendall's third appearance at the Open, and chances are he would have come over in a row boat if that's what it took. Because this is a guy who just seven years ago glimpsed the end of his professional life.
It was summer 1997, and Kendall came to the Buick Classic having just missed the cut in four consecutive tournaments. His best finish in 12 previous starts was a tie for 49th. He'd already lost his exempt status on the PGA Tour twice and was in danger of missing yet another cut.
Then Kendall hit his drive on the second fairway at Westchester Country Club, walked to where he thought it landed, and hit his approach within an inch of the hole. The only problem was that he hit the wrong ball, turning a certain birdie into a double-bogey.
Instead of losing it, Kendall turned all that anger inward. He birdied the final four holes.
'It completely turned my career around,' Kendall mused a while ago.
He hasn't come close to losing his tour card since. That, combined with the memory of pounding balls between shifts waiting on tables, is why big-timing anyone is hardly Kendall's style.
En route to an opening-round 69 a day earlier, he spotted Prince Andrew chatting behind the 11th green and asked an official walking with his group for some tips on protocol before daring to introduce himself.
'I went over and shook his hand and talked to him briefly, and that was pretty exciting to me. Seemed like a great guy,' Kendall said. 'I don't know. Is he? You guys tell me.'
Assured by the assembled grins that the prince was a regular fellow, Kendall sat back in his chair, and an embarrassed grin creased his lips. He didn't say why, but the expression seemed to speak for itself:
Is this a great game, or what?
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