Block Island Race Week’s Best Boat

This 30-year-old J/29 took home top honors at this summer’s Block Island Race Week.
Jack McGuire’s immaculately maintained J/29 won five of six races in its PHRF 3 division at Block Island Race Week, earning Boat of the Week honors. ©2021 STEPHEN R CLOUTIER

“Our win is completely due to the team we had,” says Jack McGuire, a 37-year-old yacht broker from Annapolis, Maryland, who raced with a band of brothers and childhood friends to win the coveted Everett B. Morris Trophy. “The camaraderie was unmatched.”

Trimming main and calling tactics was John Mollicone, McGuire’s coach while growing up at Rhode Island’s East Greenwich YC. His brother Josh and his brother-in-law, John von Schwarz, were the boat’s spinnaker and jib trimmers. Three longtime friends, Dave Jurkowski, Nick St. Jean and Doug Nisbet, manned the pit, mast and bow, respectively. His brother Todd helped deliver the boat and prepare it for racing.

“It was definitely a family affair both on and off the water, but Block Island Race Week always has been,” McGuire says. “I actually met my wife, Elizabeth, there eight years ago when she was handing out awards because her parents were volunteers with Storm Trysail Club. This year, we all stayed together in a house on the island with our wives and kids, who were the best shore crew a team could have. The week started off with seven kids under 7, and at one point during the week we had 10 kids out there. It was just so nice to sail hard during the day and then decompress as a team with family at the end of the day. Our house was spectacular, walking distance from downtown, so we all took turns watching each other’s kids as we went out to visit some of the local establishments. It was really nice to get out into the world again.”


Block Island Race Week served as the return of Dirty Harry after 20 months of being mothballed due to the pandemic. It sat under shrink-wrap on the hard before McGuire brought the boat to Peter Ross’ speed shop in Bristol, Rhode Island, which had completed a refit a few years earlier. As a result, the team was able to do a few events before Block Island to dust off the cobwebs. “It was amazing to be back on the water with friends and family.”

Dirty Harry’s return to glory adds another chapter to the boat’s long and storied history on Narragansett Bay. Its previous owner, John Lavin, was a legend of the local racing scene. “Growing up at East Greenwich, I always saw Dirty Harry on the mooring and knew it to be a cool race boat,” McGuire says. “Eventually, I met John and started sailing with him in my early 20s, even doing two Block Islands on the boat. He sadly passed away in 2012, and his wife, Judy, asked me to sail the boat that summer.”

When McGuire later bought the boat from Lavin’s widow, it needed some serious upgrading, and Ross took him under his wing. “He let me set up shop in his building in Bristol to help me make the necessary upgrades. By this time, I had moved to Annapolis with my wife. So, what started as a six-month project turned into a 20-month project. The boat is still a stock J/29, just everything has been updated from the 1980s. We redid the bottom, replaced anything that had a load on it, like tracks and winches, and got new sails, which is what really sets us apart. They’re designed and built by John Fries out of Connecticut—Fries Sail Design. He just knows the J/29, and our suite of sails is perfect for the boat.”


The 2021 edition of Block Island Race Week had 157 boats, including many top-tier professional programs from around the Northeast, and the caliber of the fleet was not lost on McGuire and his team, especially this year. “There is no better competition on the East Coast than Block Island Race Week,” he says. “Just watching everyone out there was amazing because clearly everyone was bringing it after a year of little to no sailing. All the divisions were competitive and deep with talent. We were in PHRF 3, which had 12 boats lining up against boats with so much experience. The Storck family in their J/80 Rumor was pushing us on the starting line every time, and Steve Thurston with his J/29 Mighty Puffin never let up as well. Everyone was just pushing hard the entire time.”

What started as a six-month project turned into a 20-month project. The boat is still a stock J/29, just everything has been updated from the 1980s.

What set his team apart from the competition, he says, were the little things on the racecourse that eventually added up to bigger margins. “It was all about getting out and finding the lane to put the throttle down, followed by our clean mark roundings. When you can hold that spinnaker until the last second before the leeward mark or execute a perfect jibe set, you just extend every time.”

Dirty Harry
Pre-event practice ensured their mark roundings were clean. One focus, skipper Jack McGuire says, was understanding the timing of maneuvers. ©2021 STEPHEN R CLOUTIER

But that didn’t come naturally. With coach Mollicone on board, the team went out for two hours the day before race week and ran a windward/leeward session, focusing especially on mark roundings. Mollicone was even timing Nisbet on the bow so he knew how much time they had to pull off the maneuvers.


Practice paid off, of course, and when they were called to the stage to accept their Boat of the Week award, McGuire was elated. “Four years previous, we had just finished the boat and launched a month before, so we were just happy to be bringing Dirty Harry back to Block in honor of John Lavin. I think we finished fourth. Then, in 2019, we really went for it. I had six of the seven crew that we had this year, and we were so close to the top and just lost out to Interlodge, which is an amazing race program, so we couldn’t be too disappointed.”

This year, however, everything clicked, he says. “We won every race except the around-the-island, and we only lost that one by seven seconds after 18 miles and with a symmetric spinnaker against so many asymmetric kites. Winning overall was our goal, and we achieved it, which is just pure satisfaction. There were many who said a J/29 could never win top boat, so seeing my name on the list of other winners of Block Island Race Week is so rewarding. Anytime your name and Ted Hood’s are on a trophy together, it blows your mind. I wouldn’t have changed that week for anything, and to then share that stage with family and close friends is just the icing on the cake.”