The Walsh family’s annual OPL Charities Golf Tournament brought golfers, business partners and friends to The Resort at Longboat Key Club for a week that built to a sudden-death putting duel and a big-top gala that raised $525,000 for a dozen charities
—Every great sport has its great rivalries. Ali and Frazier. Magic and Bird. The Red Sox and the Yankees.
—And now, Longboat Key has one of its own.
—In one corner: Mayor Debra Williams. In the other: Mark Walsh, whose family has spent decades raising money for good causes and hosts the annual OPL Charities Golf Tournament. Between them: four holes of putting, $30,000 for the Town of Longboat Key and one very excited golf pro with a microphone.
—Call it the Thrilla on the Key.
—It went down Wednesday afternoon, Oct. 28, on a putting green at The Resort at Longboat Key Club, and it went all the way to sudden death. By the time the circus performers took their final bows under the big top that night, the week had raised $525,000 for a dozen charities, plus that extra $30,000 for the town.
—Not a bad day’s work. Not a bad week, either.
—A Week for the Business Family
—The OPL Charities Golf Tournament filled the Key Club’s fairways Oct. 26–29, and it is not your average charity scramble. The tournament brings together the vendors and business partners who work with Ocean Properties all year long, which makes the week part golf outing, part charity drive and part family reunion. The family, in this case, is a business family, and it is a big one.
—OPL stands for Ocean Properties Ltd. OPL Charities, formerly known as Wentworth Charities, has spent more than two decades raising millions of dollars to fight disease and help people who need it most, from New England to Florida. It is a signature event and one of the largest charity fundraisers in the region.
—The company traces back to 1969, when the late Tom Walsh opened a single hotel in Maine. His children, four sons among them, grew it into one of the largest privately held hotel companies in North America: more than 100 properties, including the resorts of the Opal Collection and, since 2012, the Key Club itself.
—To know Mark Walsh is to know a guy from Maine. People from Maine do not put on airs. They put on fleece. The Walshes run their company the same way, and you can see it in the people who work for them. Spend time at the Key Club and you’ll meet staff who have been there for years, and a remarkable number who have been there for decades. That kind of loyalty doesn’t come from a handbook. It comes from being treated like family.
—Wednesday: The Main Event
—Every big week needs a big day, and Wednesday was it. In the afternoon, the Longboat Key Putting Challenge. In the evening, the gala. In between, a whole lot of anticipation.
—The putting challenge has become a signature Longboat event in its own right. The format is simple. Mark takes on the town’s elected officials and top brass, hole by hole, with money riding on every hole for the Town of Longboat Key. When a town official wins, Mark has been known to double the prize. The tradition runs deep. Back in 2015, a celebrity putt-off at this same tournament raised money for the town’s 60th anniversary party.
—This year’s “Putt for Dough” scoreboard read like the Town Hall directory: Mayor Debra Williams; Commissioners Steve Branham, BJ Bishop, Penny Gold and Gary Coffin; Fire Chief Paul Dezzi; Police Chief Russ Mager; Assistant Town Manager Isaac Brownman; Town Manager George Landry; and special guest Susan Phillips.
—Tale of the Tape
Left: Mayor Debra Williams puts Terry O’Hara’s favorite advice into practice: lightly, with feel and finesse, while Terry hovers close enough to read the break off her shoulder. Right: Mark Walsh lines up a putt as the “Putt for Dough” scoreboard tallies the afternoon’s challengers, a who’s who of Town Hall all lined up for a shot at the host’s famously generous charity pot.
—In this corner, wearing a Resort at Longboat Key Club cap and an expression of total focus: Mayor Debra Williams. Known for: reading every page of the agenda packet. Preparation: legendary. She was on the green before any other commissioner, practicing, walking the lines, crouching low behind the ball, testing the speed of the greens and studying every break like it was a site plan.
—And in this corner, in a gray polo with a small red B on the chest: Mark Walsh. Known for: hospitality on a grand scale. Advantage: home green. While the mayor practiced, Mark worked the crowd, relaxed and easygoing, greeting friends and business partners like a man hosting a party, which, to be fair, he was. He also knows every ridge and roll of that green, which is the kind of thing a golfer quietly takes comfort in.
—About that red B. For our readers from the New York area, it is the logo of the Boston Red Sox, and its appearance caused real distress among the Yankees fans on hand, several of whom found it difficult to concentrate on their short game. Mark has not said whether the shirt was a strategic choice. Red Sox fans would like it noted that it is never just a shirt.
—The oddsmakers, had there been any, would have had a tough call. Was the mayor the underdog? Was she a ringer with a hidden skill set? Or would the host, with all that local knowledge, come on strong at the finish?
—The Voice of the Green
The rivals and the referee: Mayor Debra Williams and Mark Walsh share a laugh with Key Club Director of Golf Terry O’Hara, who keeps an arm around each competitor, partly out of friendship and partly to make sure nobody sneaks in a practice putt.
—Presiding over it all was Terry O’Hara, the Key Club’s longtime director of golf (who also writes golf columns for this newspaper). Terry served as play-by-play announcer, color commentator and personal putting coach, often in the same sentence.
—His advice was sound. Read the break. Hit it lightly, with feel and finesse. And above all, he kept emphasizing, do not hit it off the green.
—Easier said than done. Balls skittered right off the green. Two-putts became three-putts. Three-putts became four-putts. Through it all, Terry called the action as though it were the back nine on Sunday at Augusta.
“Oh my God, you tied this up,” he would say. “But you have to make this shot. You must make this. It’s imperative.”
—They would miss.
“Oh my God,” Terry would say. “What were you thinking?”
—Jim Nantz has never been this emotionally invested in anything.
—The Undercard
Left: Commissioner Gary Coffin, whose name is helpfully embroidered on his shirt in case the ball forgot who it was working for, watches his putt pull up short. Right: Town Manager George Landry, about six weeks on the job, came straight from Town Hall with his ID badge still clipped on. A devoted pickleball player, Landry found the bright yellow ball reassuringly familiar. The rest of the sport, less so.
—Before the main event, the undercard delivered plenty of drama of its own.
—Police Chief Russ Mager made some genuine signature shots, rolling in a couple of beauties that drew real applause. No citations were issued.
—Commissioner Gary Coffin, who is a wonderful commissioner, and we want to say that first, had what golfers politely call “an afternoon.” His putts had places to go, and those places were not the hole.
—Commissioner BJ Bishop, who has been fighting to get FEMA to pay what it owes the town, discovered that the putting green can be even less cooperative than the federal government. She did not have her best day with the flat stick. FEMA, consider yourself warned.
—Town Manager George Landry, about six weeks into the job, came straight from Town Hall with his ID badge still clipped on. Landry is a devoted pickleball player, and he learned on Wednesday that golf, sadly, does not let you dink your way out of trouble.
—Every one of them putted for the town, and every one of them got a big hand from the crowd.
—Stroke for Stroke
Left: Mark Walsh rolls one toward the cup as Mayor Williams watches with the serene patience of someone who has sat through budget hearings longer than this entire tournament. Right: So close! Walsh laughs off a putt that stopped a whisker from the cup, a true sportsman in a real dogfight.
—Which brought us to the main event.
—Debra Williams knocked her very first ball into the hole. On the second, she left it within inches. A murmur went through the crowd. The mayor had clearly been listening to Terry, and practicing, and quite possibly both at once.
—Then Mark stepped up and answered. Putt for putt, hole for hole, the host matched her every step of the way, enjoying every minute of a genuinely great contest.
—After four holes, they were dead even.
—At a Town Commission meeting, a tie like that gets sent to a workshop. On a putting green, there are no workshops. There is only sudden death: one final face-off, double the money, winner take all.
—Liftoff
Mayor Debra Williams and Mark Walsh hold the $30,000 check from the Longboat Key Putting Challenge 2026, made out to the Town of Longboat Key and dated Oct. 28, surrounded by the afternoon’s competitors and hosts. FEMA, please take note: this money showed up the same day. From left: Fire Chief Paul Dezzi, Police Chief Russ Mager, Assistant Town Manager Isaac Brownman, Susan Phillips, Key Club Golf Director Terry O’Hara, Key Club Managing Director Rick Konsavage, Mayor Debra Williams, Mark Walsh, Commissioner Steve Branham, Vice Mayor Penny Gold, Commissioner B.J. Bishop, Commissioner Gary Coffin and Town Manager George Landry.
—What happened next is best explained by the photograph accompanying this story, in which the mayor of Longboat Key is approximately one foot off the ground.
—Debra Williams won it. The prize: a $30,000 check from The Resort at Longboat Key Club, made out to the Town of Longboat Key.
—As far as this newspaper can determine, it is the greatest altitude ever reached by a sitting Longboat Key mayor without the help of a parasail.
—And Mark? He joined her for the big-check photo with a grin, and we suspect he started planning next year’s rematch on the spot. Every great rivalry needs a sequel.
—Under the Big Top
Big top, bigger ball: Michael Walsh, Mark’s brother and one of the family owners of Ocean Properties, joins a circus performer for some big-ball wizardry under the big top at Wednesday night’s OPL Charities gala. After an afternoon of watching golf balls lip out on the putting green, the crowd was relieved to see a ball nobody could possibly miss. Michael, arms flung wide, appears to be auditioning for a permanent spot in the show.
That evening, the celebration moved under a big tent on the Harbourside Golf Course along Sarasota Bay for the gala, the heart of the week’s fundraising.
For more than an hour, a troupe of circus performers did things with the human body that most of us in the audience could not do with a running start, a chiropractor on standby and a signed waiver. The crowd was wowed. I was wowed. Several days later, I remain a little wowed.
When the totals came in, the week had raised $525,000 for a dozen charities. Among them: the Boys & Girls Clubs of Sarasota and DeSoto Counties, Camp Boggy Creek, the Children’s Dream Fund, The Glasser/Schoenbaum Human Services Center, Hope 4 Communities, Manasota BUDS, the Cystic Fibrosis Foundation and the Tuberous Sclerosis Alliance.
—The Final Tally
—Add it all up and the week looked like this: $525,000 for a dozen charities, $30,000 for the town, more than an hour of circus, one friendly baseball controversy and a mayor in flight.
—But strip away the big top and the putting heroics, and what’s left is simpler. A family from Maine that has made a habit of giving back in the places it calls home. A business family of vendors and partners who show up to play golf for a good cause. A staff that has stuck around for decades. And a dozen organizations that will spend the coming year turning that money into summer camp for kids with serious illnesses, a safe place to go after school and help for neighbors who need it most.
—So here’s to the Walsh family, the Key Club team, the business partners who teed it up all week, Terry O’Hara and his microphone, and one very airborne mayor.
—See you at the rematch.
