Paul Tesori was 5 years old the first time he watched the world’s best golfers compete at THE PLAYERS Championship, his hometown PGA TOUR event. Little did he know that 41 years later he’d be inside the ropes, caddying for Webb Simpson, as he won the TOUR’s showcase event. Tesori, who is one of the most respected caddies in the game, reflects on that moment, among others, in this Q&A for Essential Golf.
Tesori came by his love of golf honestly. His father was a plus-handicap at the age of 16 and later a multiple winner of the Coast Guard championship. His grandfather, who emigrated from Italy as a youngster and learned the game as a caddie in New York, worked as a starter at the Ponte Vedra Inn and Club for three decades. Guided by them, Tesori became a three-time All-American and played on a national championship team at Florida, as well as briefly on TOUR, before finding his niche as a caddie. He has worked for Vijay Singh (twice), Jerry Kelly, Sean O’Hair, Webb Simpson, Cameron Young, and Tom Kim over the past 25 years.
Q: A phone call from Vijay Singh started this great adventure, didn’t it? He asked you to fill in as his caddie at the 2000 Buick Open and the rest, as they say, is history.
TESORI: We finished 11th that week, and then he hired me the next week as his teacher, and that’s the week he got paired with Jack Nicklaus and Tiger Woods, while Tiger was going for three in a row up in Kentucky at Valhalla. Still to this day, I’m sure it’ll never be beaten with the largest crowds anyone’s ever seen. It was Nicklaus’ last PGA, Woods going for three in a row, and Vijay, the reigning Masters champ. I just remember that week. This is unlike anything that I could ever imagine. He hired me (as his caddie) at the end of that week. You’re talking to a guy that was making $20,000 a year at the time and very quickly making $20,000 a week. I obviously had to take the opportunity, and I’m still thankful to Vijay for that opportunity because here we are 25 years later and it’s all because he gave me a chance to do it. … We did some great things together, put together a plan to overtake No. 1 in the world, and I was part of the team during that entire stretch. We did some great things and still very fond of those memories, and he taught me pretty much everything I know about my job, so I’m thankful.
Q: How do you put together a plan to overtake Tiger?
TESORI: So, it was the off season of 2001. … Vijay wanted to be the best player in the world. That was his only goal. We came up with seven areas we thought that we had to take a hard look at — and this was over one of the best bottles of wine in the world. Well, we had two. We had one apiece, a bottle apiece, and we came up with this plan, basically had seven different categories and we rated them and … I think we gave Tiger putting and gave Tiger the mental game and physical game. We gave Vijay driving. Chipping, we had them really equal. … Driving, iron play, wedge game, chipping, putting, mental and physical were the seven. So, we put together a plan, how are we going to catch him?
The first thing was physically — there was something (Vijay) could do about that. So, he hired Joey Diovisalvi and he started working out twice a day. Putting, we decided we were never going to beat Tiger in putting, that’s kind of the way Vijay looked at it, so we gave in on that one. But we thought we could become better wedge players. So, every day he did wedge work between 50 and 110 yards, and he went to work on some mental stuff, as well. Learned a lot of tricks when it comes to breathing and stuff like that, worked on Tai Chi. Those are the plans he put together. Sure enough, it took about a year for it to start really taking place where we started winning, then about a year and a half till he started winning at such a high clip that he was getting closer to Tiger and finally overtook him in 2004, which would’ve been about two and a half years after we put the full plan in place.
Q: As long as we’re talking about you and Vijay, I need to ask you about the “Tiger Who?” hat.
TESORI: It’s still one of Tiger’s favorite stories that he makes me retell. … It was my third event caddying in the Presidents Cup. The United States only needed, I think a point and a half to win the Presidents Cup on Sunday. That’s how big of a blowout it was. We had played Tiger in three of the four matches, and we drew him again in singles. So, these ball guys had 12 hats made up for the International Team. The story is that they had everybody sign their flag; 23 of 24 guys sign it; Tiger didn’t. So, they had these hats stitched with “Tiger Who?” We thought it was funny. I asked Vijay what he thought; he thought it was funny. So, we were on the fourth hole of our singles match, and Vijay had a 10-footer for birdie. We’d already given Tiger a 20-footer for bogey, and Tiger didn’t give him the putt, and Vijay lagged it up to a millimeter – wasn’t even a millimeter, half the ball was hanging over the hole — and Tiger didn’t give it to him. So, we realized he didn’t think it was funny. … All of a sudden, he was 7 under in his last 13 and beat us 2 and 1. So it was something, again, I regretted for a long time. People thought I was being disrespectful. People thought Vijay was being disrespectful. We got paired together with Tiger the next five weeks, and I eventually had to say something to Tiger. I’m like, bud, I had no idea. When I walked off the course that day, I was surrounded by seven media outlets: USA Today, New York Times, AP, everybody. … I didn’t realize what was going to come. And of course, Vijay was like, Pauly, don’t worry about it. He kind of liked his back up against the wall. Long story short, my favorite part of this was he accepted my apology. …
It was a good solid 12 years before we talked about it again. I was working for Webber. Tiger loves Call of Duty, and he always talks about he can’t find a screen name. … So, he’s walking by the putting green. I said, Webber, look at this. I’m going to get him. I said, Tiger. He goes, yeah, Pauly. I said, I got your new Call of Duty screen name — Tiger Who? He goes, yours should be 2 and 1, and he kept walking. Now, remember, we have not talked about it once. So that means as soon as he sees me, he thinks 2 and 1. And he turned around with that big grin he always had and laughed as he was walking off. … He’s had me tell the story pretty much every team event because he loves the arms crossed, not giving Vijay the millimeter putt and all that. But yeah, people kind of have the wrong idea of what that was. But I think as I’ve gotten older and people have gotten to know me, they realize that there wasn’t any ill intent.
Q: After several successful years together, Sean O’Hair fired you in October of 2010. What was a kick in the pants, though, became one of the best things that ever happened it you, right?
TESORI: We were still top 30 in the world. … and I mean, I was shocked. That was the big crash, part of my testimony, where I had lost everything I’d ever had, the huge real estate crash. I had all my money in real estate, and I didn’t know what I was going to do. But in December of ‘10, I had opportunity with Dustin Johnson and Camilo Villegas who were both, one was top 10 in the world, one was top 15 in the world, and I ended up choosing lowly number 213 in the world, Webb Simpson. I had just come into faith in the summer of 2010, and I wanted to have a man to go work for who was a Christian, who walked with the Lord. And that was Webb. People thought I was nuts, absolutely nuts. I kind of thought I was nuts too, but I’d made a promise to myself and my family that I was going to seek out a believer.
Lo and behold, that year, he finished second on the money list, second in the player of the year voting, and a year and a half later won the U.S. Open, top five in the world. We had an incredible 13-year run together with seven wins, six team events, and he became my best friend very, very quickly. So, what a special, special decision that I believe the Lord definitely helped me make, that my faith led me to. Again, on paper it looked like a crazy thing, but it kind of cemented who I was at my job and the ability that I had to do it well.
Q: You’re back with Webb in 2026. Family was a big part of that decision, right?
TESORI: I’ve never experienced what I experienced this summer. I was home for 13 weeks (after he and Tom Kim split). I got to be a dad and a husband for the first time pretty much in my whole life. And it was incredible. I don’t know how else to explain it. It was the most special time of my entire life. My son flourished, my wife flourished, and it’s because I was home and it was beautiful to see. I had some really lucrative and great opportunities this late summer and fall but at the end of the day, Webb was very generous and offered me a nice salary to come back for a year. Webb’s only going to play 11 events this year. He’s only going to play about the same thing next year, and the ability to be home that much and still make a really good salary was too much for me to pass up. … So we’ll see what the future holds, but I’m definitely excited to go back. I’m still teaching Webb full time as his coach so it kind of made sense to marry the two together again for a year.