For competitive mid-amateur golfers, summer can feel at times like a vacation. That’s when they tend to play most of their tournaments, often at very special venues and with their wives or significant others along for the ride. Those elements alone make the events good fun for one and all. And they can turn into a downright party for those who emerge victorious.
Jimmy Chestnut understands that after his summer of good golf. First, the 42-year-old lawyer from Bloomfield Hills, Michigan, captured the mid-amateur division of the Anderson Memorial Four-Ball at Winged Foot outside New York City in mid-June with his friend and fellow Oakland Hills Country Club member Scott Strickland. Then a week later, Chestnut triumphed in the mid-amateur division of the C.B. Macdonald Amateur Invitational, aka The Singles, at the National Golf Links of America on Long Island, New York.
That is quite a run, and what made it even better for the Michigan State graduate was that his wife of 14 years, Michele, was in attendance for the second of those wins. Pregnant with their first child, due to be born in November, and a partner in the accounting firm of EY, she had come to New York after the Anderson. They stayed in an Airbnb in the city for the first part of the week, working out of offices that each of their firms maintains there. Then, Jimmy, who works for the consulting firm AlixPartners, and Michele headed to the East End of Long Island for the Singles.
A couple of months later, Chestnut’s summer drew to a close at the Crump Cup at Pine Valley, where he made it through qualifying for match play but lost in the first round of the third flight.
“I really enjoy competing. ... I love how it gives me the chance to play against some really good golfers at some really great courses and clubs, the sort of places I dreamed about playing.”
jimmy chestnut
Born in 1982, Chestnut lived initially in El Paso, Texas, where his engineer father was residing after opening a GM automobile plant in Juarez, Mexico, just across the Rio Grande. From there, the family moved to Rochester, New York, and eventually Grand Blanc, Michigan, just south of Flint and some 60 miles northwest of Detroit.
“We joined the Warwick Hills Golf and Country Club when we moved to Michigan,” said Chestnut, who has two older sisters. “And that was when I became interested in golf. My father played, and that was one way for me to hang out with him. Warwick Hills also hosted the Buick Open for a number of years, and I would go out there during the tournament each year and follow the pros around.”
Chestnut says he was 12 years old when his family became members at Warwick Hills. “That’s when I started playing golf, but it was not until I was in high school that I began getting somewhat serious about it. I made the golf team but was not in the starting lineup. I was a better tennis player back then.”
But he became skilled enough at golf to play at Michigan State. “We won the Big Ten championship my senior year,” Chestnut said. “One of my teammates was Ryan Brehm, who was a sophomore and went on to win a couple of tournaments on the Korn Ferry Tour [known then as the Web.com Tour] as well as the 2022 Puerto Rico Open on the PGA Tour.”
Chestnut graduated from MSU in the spring of 2005, having majored in political science and economics. He tried professional golf, but after failing to get through Q-School that fall or succeeding on the Hooters and Adams mini-tours in subsequent months, he applied to law school at Michigan State.
By the time he earned his law degree, Chestnut had regained his amateur status – and had managed to win some significant tournaments in his adopted state, among them the 2008 Michigan Amateur and the Golf Association of Michigan Championship. Not surprisingly, the GAM named Chestnut its player of the year after those performances.
That same season, he also qualified for his first U.S. Mid-Amateur, at Milwaukee Country Club in neighboring Wisconsin, making it to the quarterfinals before falling to Sean Knapp, 2 and 1.
Chestnut and Michele married in 2010, after meeting in Grand Blanc during high school and attending MSU together, and they pursued their respective careers. For Chestnut, that included a two-year stint working for the CIA at its headquarters in Langley, Virginia.
“I didn’t do any of the juicy stuff,” he said, “but it was cool to say that I worked there.”
In time, they moved back to Michigan, where Chestnut settled into a competitive routine that entailed playing a half dozen or so tournaments a year, first as a member of Detroit Golf Club, where he captured club championships in 2014, ’18, ’19 and ’20, and then historic Oakland Hills, where he took that association’s club championship in 2022 and ’23. Along the way, Chestnut prevailed in a second GAM Championship, in 2020, and has now qualified for nine USGA championships.
“I really enjoy competing,” he said. “And it is great that I have an avenue to do so with golf. I take it very seriously, but not so much that I make myself crazy with it. I love how it gives me the chance to play against some really good golfers at some really great courses and clubs, the sort of places I dreamed about playing.”
Such as Pine Valley, for this year’s Crump.
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Top: Jimmy Chestnut during the 2019 U.S. Mid-Amateur
Chris Keane, usga