The Lawyer as Swinger

It’s Doug Clapp’s big moment. He’s near the first tee of New York’s Oak Hill Golf Club in 1998, making his first appearance at the United States Amateur Championship. The announcer calls his name — it’s his turn to tee off. He kisses his wife, who is pregnant with their first child, and walks to the tee box. A whole lifetime of playing golf, those hours and hours out on the course, has led to this one moment. He’s standing at the tee. What happens next? Ask someone else, because Doug can’t tell you.

“I still have no recollection of that first tee shot,” the 37-yearold Clapp says. “The next thing I remember is talking to [my caddy and co-worker] Jim McDermott about whether we should hit an eight iron or a seven into the green. It’s all at once the least memorable and most memorable moment for me on the golf course.”

The memory of that first tee shot may be gone, but Clapp, a partner and business law attorney at Holland & Knight, has made plenty more — he’s played in two more U.S. Amateur Championships and also competed in the British Amateur Championships. He even made it to match play ranked seventh in last year’s Mid-Amateur Championship. Not too shabby for a guy who has only had one real golf lesson in his life.

Clapp picked up golf like any other kid — by literally picking up his dad’s three iron at age 11 after the elder Clapp had participated in a charity tournament. “I grew up in Pittsfield, Maine, at a time when golf wasn’t booming,” he says. “I was a baseball player, and I just did whatever it took to put the ball in the hole.”

“Whatever it took” must have worked pretty well, because Clapp’s sweet swing won him the Maine State Juniors in 1983. After playing on his high school’s golf team at the Maine Central Institute, Clapp joined the team at Amherst College (where he took his one golf lesson). “My senior year I finished tenth in the nationals and then gave it up when I went to law school,” he says.

“I never really did consider going pro — I knew I wanted to go to law school because my father was a lawyer and a judge,” he says. So Clapp enrolled in Boston College Law School, where golf coursework took a back seat to legal coursework. “I didn’t really pick it back up or compete in any tournaments until I started working at the firm,” he explains.

For 12 years, Clapp and Jim McDermott, another partner at Holland & Knight, have organized winter trips to golf courses in warmer climates. And the friendship goes deeper still — McDermott has caddied for Clapp for nine years at the state amateur championship. “For all intents and purposes, particularly back then, he was my boss. There are a lot of jobs where I wouldn’t have the ability to set my schedule to play in this stuff,” Clapp says. “Getting that kind of support is really instrumental in being able to do this.”

What does Clapp do when he’s not adjusting his schedule to hit the links? “We’re kind of a niche practice,” he explains. “We represent the equity investors in affordable housing projects. Investors put money in and take away tax benefits, and we syndicate those projects and put partnerships together with developers.”

Perhaps it’s a job that may not sound thrilling to a young lawyer, but colleagues McDermott and Bill Machen convinced Clapp to give it his best shot — and they even gave him a mulligan. “I made them promise that I could go back [to being a litigation associate] if I didn’t like it,” Clapp says. “But six weeks in, I knew I was never going back. I was very comfortable in that environment, negotiating the deal.”

Clapp’s greatest moment, however, came neither in his legal negotiations nor on the greens. In 1994, he sunk a putt he’d been lining up for 10 years when he married Jana Morra, his high school sweetheart. “She doesn’t play golf, but very few husbands get the support that I get,” he says. “And Jana professes that if [our 6-year-old son] Jeffrey sticks with it, she will give it a try.”

Turns out Jeffrey is a chip shot off the old block, becoming a junior club champ in his age group. Looks like the Clapp men might need to get Mom some clubs.