Bangor lawyer Jeffrey Silverstein will sail this boat from Kittery to Lubec to raise money for cancer care to honor his friend and the boat's former owner Julio DeSanctis. Credit: Courtesy of Jeffrey Silverstein

As Julio DeSanctis was nearing the end of his life eight years ago, the legendary Bangor attorney gave his colleague Jeffrey Silverstein gift — a Windrider daysailer.

Credit: Courtesy of Jeffrey Silverstein

In July, Silverstein will sail the 16-foot kayak with two hulls more than 250 miles from Kittery to Lubec to raise money for cancer research and treatment in memory of his friend.

DeSanctis died in September 2011 after a nine-year battle with cancer. He was 67.

DeSanctis was a solo practitioner who was a fixture in the courthouses of northern Maine for more than three decades beginning in the 1980s when he and family moved to the state from Pennsylvania.

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Only judges during formal court proceedings addressed him as “Mr. DeSanctis.” Outside the courtroom, he was always Julio. When he ran unsuccessfully for the state Senate in 2008, his bumper stickers and signs read simply, “Julio!” Everyone who knew him understood and agreed with the exclamation point.

“Julio had a short-lived career as one of the world’s most interesting taxi drivers before turning his attentions to what would become his lifelong pursuit, driving other attorneys, judges, clerks, cops, witnesses and criminals nuts,” his family wrote in his obituary. “In what could only be described as a ravenous desire for justice — and perhaps a bit of just always wanting to be right — Julio stood head and shoulders above the crowd. After over 35 years of defense work his reputation for pugnacity and as a champion of the underdog is unparalleled.”

Silverstein, 58, of Bangor decided the best way to honor his friend was to raise money using DeSanctis’ sailboat for Northern Light Health Care’s Champion the Cure Challenge, which has raised money through other kinds of events.

As of Sunday afternoon, Silverstein had raised $2,655 toward his $5,000 goal through Northern Light Health Foundation.

“I will make this sail without any financial backing or assistance,” Silverstein said in announcing the event. “I do have sailing experience, but sailing the entire coast of Maine in a small boat will be new to me and a good opportunity to make a small impact in tribute to my buddy and in furtherance of local cancer care and research.”

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Silverstein said that he will start at Whaleback Light off Kittery and end his journey at West Quoddy Head Light in Lubec. He expects the journey to take seven to 10 days and will be able to signal for help if he runs into bad weather.

The only modification Silverstein has made to DeSanctis’ sailboat is to add a jib, so the Windrider now has two sails, the original large sail and a smaller one.

The attorney and sailor has joined the Maine Island Trail Association. He will stop overnight at spots along it and friends who live along the coast have offered him a bed and a hot shower. He also will be able to get provisions along the route.

“I may go out a couple of miles offshore,” Silverstein said. “There’s no huge distance that can’t be negotiated with intermittent stops. Crossing Penobscot Bay may be challenging.”

Silverstein said he would be updating the Facebook page, Sail for the Cure; Whaleback to West Quoddy Head, 2019, dedicated to his trek.

To donate to the event, visit or call 973-5055.

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