Webb Simpson and his caddie Paul Tesori have forged a bond that goes beyond the course

The San Diego IHOP was offering all-you-can-eat pancakes that Saturday morning. Paul Tesori wasn’t about to back down from a challenge when his new boss, Webb Simpson, asked how many he could eat.

“I think I can eat 13,” Tesori replied.

“No way,” was Simpson’s retort.

So Tesori proceeded to down a total of 15, just for good measure. And with that somewhat dubious gastronomical decision – “You can imagine what that did to my system,” he said, laughing at the memory now -- the tone for the day was set.

Simpson had just missed the cut at the 2011 Farmers Insurance Open. It was just the third tournament in which Tesori had caddied for the Wake Forest graduate, and the two were headed to a nearby course to practice.

And they did. For hours and hours. They even challenged each other to an anything-you-can-do-I-can-do-better chipping contest that had the cart guys watching and egging them on.

“We were banking it off buildings, off walls, hitting it out of trees,” Tesori remembered.

As much as they laughed, though, the two men also had time for more serious discussion. Simpson was just a couple of years out of college and he’d had just six top-10 finishes in 61 PGA TOUR starts. He wanted to take the next step, and Tesori had some ideas on how to do it.

“We talked about the process of getting better,” the veteran caddie recalled. “We talked about the areas that I thought he needed to do if he really wants to be elite, what we needed to change, how we needed to change it, how we needed to get better and then put that process into play.”

Simpson did indeed get better. He won the 2012 U.S. Open, then six years later, he won THE PLAYERS Championship. Those two victories meet the criteria for World Golf Hall of Fame eligibility when Simpson turns 45 in 2030. All told, he has seven PGA TOUR wins, including two this season, and he enters this week’s Wyndham Championship ranked third in the FedExCup standings and sixth in the world.

His bond with Tesori, meanwhile, is stronger than ever, among the longest player-caddie relationships on the TOUR. After two weeks apart while Tesori battled a back injury, they’re reuniting at Sedgefield, where Simpson won in 2011 and has six other top-10s in 11 career starts. And both men point to that 15-pancake day in San Diego as pivotal in their partnership.

“I feel like that was where our friendship was really born, or formed,” Simpson said. “We spend all day together, we love hanging out with each other, we talk about great things, we laugh a lot, we love similar things away from the game like the NBA. ...

“I truly think it is one of the deepest friendships that I have.”

Tesori agreed.

“It was just a truly special day,” he said. “... Just talking about it now brings back some really good memories. That was the day for sure everything changed. We became friends that day.”

The business relationship began with an out-of-the-blue phone call in December 2010, a few hours before Tesori had planned to take a job with Camilo Villegas, then a three-time TOUR winner who wanted to hire Tesori after Sean O’Hair let him go.

Tesori, who had never been fired before, had quite the resume. He had worked for future World Golf Hall of Famer Vijay Singh – twice -- as well as Jerry Kelly and O’Hair. At the time, Tesori had two solid job offers – the other was from Dustin Johnson, who at that point had four TOUR wins – but he was looking for the right fit.

“I just didn’t think I could help Camilo,” he said. “I really like him, but I've always wanted to be in a place where I felt like I could help a player get better. Somebody who is open to hearing ideas, who is open to trying new things to get better.”

Enter Simpson. His previous caddie, one of his best friends growing up, had left to become a pastor in Savannah. Simpson knew Tesori was between jobs, so he took a shot.

When he hung up the phone, Simpson’s wife Dowd asked how the conversation went.

“I said I think it went really well, I said yes, but I got interviewed instead of him,” Simpson recalled with a laugh. “He just had lot of questions about my goals and desires and work ethic, and I think he just wanted to make sure it was right fit for both of us.”

Tesori didn’t know Simpson well, other than the fact that he was young (25 to be exact) and a fellow Christian. So while they talked, Michelle – Tesori’s girlfriend at the time and now his wife -- Googled Simpson. He was ranked 213th in the world and had barely kept his card that year, tying for eighth at the Wyndham Championship to move from 137th to No. 121 in the FedExCup at the regular season finale.

Compared to the other players interested in hiring him, it seemed like something of a mismatch.

“I know he has made that joke that I interviewed him, but I did,” Tesori said. “I had a lot of questions. I have felt like there's been times in society where great athletes who are Christians feel like maybe they're not supposed to be great.

“I do not fall in that category. I think that God gives people talent to be used to create a platform that they can then use to talk about their faith -- and to make an impact on society. Webb, you could tell by his voice, you could tell that he wanted to be great. You could tell that he wanted to do the right things.”

Simpson agrees that their shared faith – Tesori was baptized six months before the two met -- and the opportunity to help him develop likely were the deciding factors in their partnership.

“We talk about our faith on and off the golf course ... and I think maybe he wanted that, and ultimately, I think prayer is what led him to say yes,” Simpson said. “I think he and Michelle prayed about it and felt like God was leading him in my direction.

“It didn’t make a whole lot of sense, world ranking-wise. I think he had job offers from a couple of pretty highly ranked players. But I think praying about it with Michelle led them to feel like God was saying, ‘Come be a caddy for Webb.’”

A month later, Simpson and Tesori made their debut at the 2011 Sony Open in Hawaii. Tesori set several aggressive goals for the team that year – seven top-10s and 14 top-25s, both totals more than Simpson had combined in his career – as well as advancing to the third FedExCup Playoffs event and earnings of $2 million.

And how did Simpson respond? Well, he had 12 top-10s, 21 top-25s and finished second in the FedExCup and on the money list with earnings of more than $6 million. And while Tesori hadn’t set goals for wins, Simpson picked up two at the Wyndham Championship and the Deutsche Bank Championship.

“When I look back on it, I just learned a valuable lesson -- don't put limitations on what God can do,” Tesori said. “Because I saw it happen right in front of me. And he went from 213th in the world to 10th by the end of the year.”

Simpson remembers having an “Eureka” moment in their second tournament, now known as the American Express Championship. He was planning to lay up on a short par 4 with a hybrid and Tesori asked him why. Simpson said he wanted to lay up to a good number.

“And he said, ‘Well, you’re laying up to the tightest part of the fairway -- driver actually widens everything up,’” Simpson recalled. “And so instantly with that decision, I realized I’d been thinking golf courses wrong all along. ...

“He really opened my eyes to the best way to play each hole that we're encountering, and that's really changed my thinking on the golf course. I think that's why I was able to have some good finishes early on with him.”

Two weeks later, the team picked up its first top-10 when Simpson tied for eighth at the Waste Management Phoenix Open, shooting a pair of 67s on the weekend after a second-round 66. Simpson called it at “great moment” because he felt like he was getting better with Tesori on the bag.

“He could see my desire to improve and to get better,” Simpson said. “I could see his wealth of knowledge on the golf course. Not only the golf course but the golf swing. And I think the more you trust someone, it's almost like that trust that keeps growing and growing and growing. And that just stuck.”

It helped that Tesori had played golf at the highest level. While playing for the University of Florida, Tesori contributed to two Southeastern Conference titles and an NCAA crown. After that, he also made it through the TOUR’s grueling six-round q-school in 1996.

“I knew Paul had been there in big moments,” Simpson said. “... He understood what I might be feeling in a certain moment of the golf tournament, whether I'm uncomfortable or if I'm struggling with something here or there. He understood it.

“I think that's what makes certain caddies great, is that there are moments where they understand the emotions that we're going through, and it helps them be better caddies and make better decisions.”

Tesori, on the other hand, thinks that “failing as abundantly as I did” -- he didn’t make a cut in 21 starts on TOUR – has made him a better at his job because he understands the fine line between good golf and elite golf. He also learned a lot from Singh, whom he calls a “golfing savant.”

“I learned that there's a process in play and that if you don't have a process in mind for how to get better at each aspect of your game, then you won't get better,” Tesori said. “You will get behind and you can't reach your goals. And so, Webb really took to that. ...

“And here we are 10 seasons later, and that's our goal every week. It's the same thing. Still trying to get a little bit better in our putting, a little better in our chipping, a little better with our irons, a little better in our driving, think a little better. And I had a lot of tools to do that.”

When Tesori first started working for Simpson, the pro’s long-time instructor was Ted Kiegiel, the director of golf at Carolina Country Club in Raleigh, North Carolina. Tesori was Kiegiel’s stand-in on the road, and then for a year or so, he was the sole keeper of the swing.

But in 2014 as the two were on a plane, returning from an event in Japan, Tesori suggested Simpson go see Butch Harmon.

“My reasons why were that I see too many things that we need to work on,” he recalls. “There's too many areas in the golf swing that we need to piece together to get where we want to get to. And I don't know how to put them in order, and I don't want to get the order wrong, or I could hurt your game.

“And I think it was in January of ‘15 or maybe the winter of ‘14 that we flew up to see Butch and I can't say enough about Butch Harmon. He has this amazing ability to have a ton of information but gives you as little as you need. And I really saw it so much.

“And each time while I've been Webb's coach, there's always been a professional there with me helping guide my eyes or guide my thoughts. And me also helping them guide their thoughts with what Webb is trying to do. And I love that aspect, I love that little coach’s role, I love watching people get better.”

So, when Simpson goes to see Harmon now, so does Tesori. The two are in frequent communication, and Tesori remains the bridge between coach and student.

“He's got an amazing eye,” Simpson said of his caddie-turned-surrogate swing coach. “He’s constantly videoing, looking at my swing currently, comparing to old videos. Every time that it seems like I’m a little off and he sees something, and we change it and it has instant impact. It makes a huge difference.”

One example of how well Simpson and Tesori work together was at the RBC Heritage earlier this year.

They came to Hilton Head after missing the cut by four at the Charles Schwab Challenge, the first event after the TOUR returned to action following a three-month break due to COVID-19. It was disappointing because Simpson had four top-10s, including a win and a playoff loss, in five starts before the hiatus.

Tesori noticed Simpson was rushing the transition in his backswing. He was also sliding through the ball instead of rotating through it. And both player and caddie noticed two tweaks he needed in his putting: Simpson’s hands had gotten too low at address and his ball position with the putter was too far back.

“So those were a couple that very quickly paid off and we ended up winning that golf tournament that week,” Tesori said. “Which I thought it was a big momentum boost after missing the first cut. He was hot going into the pandemic and to miss the cut and come back was awfully nice.”

Their friendship notwithstanding, there are occasional arguments on the golf course. Tesori, who is 12 years older than Simpson, characterizes the relationship as a lot like a marriage and estimates there might be one disagreement a month that is more than a 15-second blip that quickly goes away.

At the 2017 PLAYERS Championship, the two hit upon a system that minimizes any potential conflict once the tournament begins. During the first round, they got into an argument at the seventh hole over whether to hit driver (as Simpson wanted) or a 3-wood (as Tesori suggested).

Simpson won out, drove it right and made bogey. Both men were frustrated but when they talked about the incident later, they came up with a plan. Prior to each round, they would take the yardage book, consider the wind direction and talk about what club to hit on each hole.

“We really try to get our arguments out before the round starts so when we're in the moment, we're not talking about what club we're going to hit or arguing about it,” Simpson said. “We've already, in a way, had our argument, and we're a lot more clear on the golf course. It helps us a lot.”

Tesori said the approach has made a world of difference.

“That has drastically made things better, in our relationship overall as friends, and in our relationship as a player and a caddie,” he said.

Off the course, there are only two things they disagree upon, according to Tesori.

One is Simpson’s love for coffee – “I think he would give up food before he’d give up coffee,” the caddie said. The former Wake Forest standout even travels with his own pour-over machine.

“You grind your own beans, you weigh the beans, you measure the water and you get the right temperature and all that,” Tesori said. “So, it makes a perfect cup of coffee. And I will say this ... it is a good cup of coffee when I've had it. I just still don't desire it.”

The second thing? Unlike Simpson, Tesori is more than happy to hang out in the hotel room. With the COVID-19 restrictions and the TOUR’s focus on maintaining a safe bubble for its constituents, the two have been rooming together – and eating in -- at nearly every tournament stop.

“So, the pandemic has definitely affected Webb probably more than most because he hates just sitting in a hotel room,” Tesori said. “He'd much rather go to a Starbucks or a cafe or a restaurant, and eat, sit out. Where I like to go into the room and put my feet up and chill.”

In the last decade, Simpson and Tesori have also helped each other through major markers in their lives.

On the golf course, they coped with the USGA’s decision to ban the anchored putter Simpson used all his life. Off it, both have become fathers – Simpson five times over, and Tesori, for the second time, to a sweet young boy with Down syndrome. Two years ago, Simpson’s father, Sam, the man who introduced him to Dowd, died after a lengthy battle with Lewy Body Dementia.

“Webb's impact on my life, goes so far beyond golf,” Tesori said. “... I just look up to the man in every single aspect of his entire life. I want to be the dad that he is. I want to be the husband that he is. I want to be the friend that he is, the follower of Jesus that he is, the brother that he is. The guy at times doesn't seem real to me. And he gets bashful and he actually doesn't like it when I talk like that.

“But it's just the way I feel. And a ton of people feel that way too. He is the most kind human being I've ever been around, and well-rounded person. And it's been wonderful to get to know him, to watch him grow over the last 10 years, too.”

To find players and caddies who are friends certainly isn’t unusual. But Simpson thinks their shared faith, as well as Tesori’s ability to function as his swing coach on the road, sets their relationship apart from many others on TOUR.

And truth be told, he’s a little surprised to have found such an enduring partnership.

“But I’d always looked at Phil (Mickelson) and Bones (Mackay) and thought I would love to have that one day,” he said. “I would to have the great friend that's with me through the highs and lows of a career .... I hope Paul's with me until I'm done. As long as he can make it.”