Jon Lester #34 of the Chicago Cubs reacts after striking out Matt Holliday #7 of the Colorado … [+]
Sixteen years in Major League Baseball is nothing to shrug off. Especially when you consider that Jon Lester’s time also consists of a remarkable 200-117 win-loss record and a trio of World Series wins—two with the Boston Red Sox (2007 and 2013) and one with the Chicago Cubs (2016).
But the down-to-earth former starter would tell you that another sport played with a white ball brings out the best in him as an athlete and someone who loves life.
Lucky for me, I was able to catch Jon Lester right after he finished Round 2 of the Hilton Grand Vacations (HGV) Tournament of Champions last Friday, January 20, in Orlando, Florida. During the second day of the LPGA’s first golf event of 2023, Lester was grouped with fellow ex-baseball men and World Series winners A.J. Pierzynski and Clay Buchholz.
“Today’s round was surprisingly good. Probably the best I’ve ever played in one of these things,” Lester said, to start our interview outside Lake Nona’s clubhouse.
Lester admits that when he was an active pitcher, he didn’t get out and play golf the way that a lot of Major League Players do, either for recreation or to relieve stress.
“I didn’t play a lot then. But now I play a little more frequently,” Lester said. “My first summer at home (post-MLB career), my wife gave me free rein to play, which was awesome. I get out there enough.”
But does playing golf, especially alongside Buchholz, with whom Lester won a World Series in Boston, or with the outspoken Pierzynski, a catcher who won a Series with Chicago’s other baseball team, the White Sox, in 2005, stoke Lester’s adrenaline or turn up any trash talk on the greens?
Lester’s answer was a humble one, but probably not unexpected for anyone who’s watched him over his long, successful career.
“For me, it’s just getting to play—and not embarrassing yourself,” the 6-foot-4 right-hander said. “And then if you actually play well, make good shots, that’s really it.”
Lester adds that before this year’s installment of the HGV Tournament of Champions, he’d never played golf on TV. Each year the HGV brings together the top women in LPGA golf with celebrity players, many of whom are sports legends, hailing from Major League Baseball, the NFL, the NHL, pro tennis, and other pursuits.
Jon Lester hits a shot from the bunker on the seventh hole during a Pro-AM before the PGA TOUR … [+]
In each round, world-ranked LPGA players such as Nelly Korda, Brooke Henderson, and J.Y. Ko will play rounds grouped with the celebrity players. Last week, the world No.6-ranked Henderson dominated each round of the HGV and won the event by four strokes, finishing 16-under-par overall.
“My first couple years (playing golf), we spent more time looking for golf balls than I did playing,” Lester said quite frankly. “Now it’s more about the idea of having fun, making shots. Playing with Buck (Buchholz) and A.J. (Pierzynski) it’s just like a round with the boys.”
Lester said that the more he gets to play in celebrity golf events, “the more you can block out” the distractions and not worry about not making good shots.
“Obviously, alcohol helps,” he joked.
But Lester also said that being around the best women in the game of golf has its own weight and does, he thinks, make ex-MLB players like him take every hole seriously.
After talking golf, I asked Lester about his time with the Chicago Cubs and about his relationship with longtime friend and catcher David Ross. After Lester and Ross helped the Cubs win the 2016 World Series, Ross retired from the game but was appointed to manage the Cubs, starting in 2020.
The duo not only took to the field in Chicago but were also a productive pitcher-catcher pair for years with the Boston Red Sox.
“The thing about us is that I could tell him he was full of it, or he could tell me I was full of it, and we just had that kind of relationship,” Lester said of Ross, a 15-year veteran of pro baseball.
“It went both ways, and we knew what was on the table, what we were trying to do. And if he knew or I knew something wasn’t right, we could hash it out and move on. I think that’s why we worked so well together.”
Lester described Ross as a cool, calm, stabilizing force.
“He was a fastball-dominant calling catcher and I was a fastball-dominant pitcher. I had to throw my heater, I had to throw my cutter,” Lester said, “and he understood all that.”
Lester (right) and Ross (center) with Chicago Cubs teammates during the 2016 World Series victory … [+]
Lester also said that their personalities “just worked” together and that “it’s easy to describe but hard to (understand) unless you’re in it.”
When I asked Lester about Ross’s return to the Cubs, first as a special assistant and then as the Cubs’ manager, a mere three seasons after they won the World Series together, Lester pegged the longtime Cubs fan favorite known as “Grandpa Rossy” as someone ideal for the role. In short, Lester said he did see Ross going into management.
“I thought it would be a little bit later than when (Ross) did. I really see all catchers going into management at some point,” Lester said. “As players, they always have the field in front of them and always know what’s going on. They’re just a different breed.”
Read Frye’s interviews with Bernie Williams and Jennie Finch
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