James "Jamie" Freeman O'Hare

On Friday, October 23, 2026, James Freeman O’Hare, “Jamie”, 67, of Winthrop, Massachusetts, died unexpectedly. In his final hours, Jamie was doing what he loved — having fun in his garage, surrounded by the engines, tools and projects that brought him so much pleasure.

Born in Boston, Massachusetts to the late Francis X. O’Hare and Etna Lynwood Freeman O’Hare, Jamie grew up in Marblehead, Massachusetts. His childhood was filled with adventures on the water in his Boston Whaler and winters spent downhill skiing. His love of adventure, and figuring out how things worked, stayed with him throughout his life. Jamie genuinely loved being alive. His devotion to family and his enthusiasm for life were constants throughout his years.

A gifted inventor and mechanic, Jamie owned at least one or more of everything with a motor — boats, motorcycles and e-bikes. For Jamie, there was always another idea to explore, a machine to improve, or a challenge worth solving. Jamie studied mechanical engineering at Northeastern University. He opened a motorcycle shop in Marblehead that he ran for a decade. Jamie then went on to build a career working with medical technology, devices and somehow always found his way back to motors. His work included refining heart valves and developing and improving medical equipment.

Retirement gave Jamie the freedom to follow where his curiosity led. He spent his days in his garage focused on customizing his motorcycles, ‘flying’ in his restored speedboat and riding his e-bikes along the coastline near his home in Winthrop. He had also started the restomod of his beloved Mustang, which he had been working toward for more than 40 years.

Jamie is survived by his beloved daughter, Kalen Regal O’Hare; his loving longtime partner, Laura Mondano; and his former wife, Stacey Regal-O’Hare, with whom he maintained a close friendship. He is also survived by his older brother, Francis X. O’Hare of Tacoma, Washington; his sister, Patricia O’Hare Williams of Marblehead, Massachusetts, with whom he shared an especially close lifelong bond; and seven nieces and nephews. He was predeceased by his cherished daughter, Mckenzie O’Hare, and sister, Margarette Cook.

There was always one more thing Jamie wanted to build. His passing came without warning, leaving those who loved him with countless memories and “Jamie stories” to share. A Celebration of Life to honor Jamie O’Hare is planned for Sunday, November 8, 2026. We will gather first for a Memorial Service at Eustis & Cornell of Marblehead 142 Elm Street from 2:00-4:00 PM. Following the memorial, family and friends are warmly invited to join us for a Celebration of Life at the Gerry 5 VFA, 210 Beacon St., Marblehead, MA, from 4:30-6:30 PM.

In lieu of flowers, the family kindly requests that you consider a donation to the VHL Alliance at vhl.org. Fond memories and expressions of sympathy may be shared at eustisandcornellfuneralhome.com for Jamie’s loved ones.