Westport has truly lost a "Living Legend".
Roland M. Massey, Jr., 87, of Westport, passed away at Royal Fairhaven Nursing & Rehabilitation on January 5, 2026. He was the son of the late Roland M. Massey, Sr. and the late Alice E. (Boudreau) Massey.
Mr. Massey was born in Westport and had been a lifelong resident of the town. He was a 1956 graduate of Westport High School. A veteran of the U.S. Army, he served his country during the Cuban Missile Crisis. He had his 100 ton Maritime Captain's License. He worked for F.L. Tripp & Sons, Inc. in Westport for over 35 years and was the best Johnson/Evinrude outboard motor mechanic in the entire area.
He loved nature; hunting with his father; fishing for stripers all weekend on his boat "Fish Tales"; shooting a good game of pool (he could definitely give you a run for your money); riding horses; sunsets on his boat "Reward" alongside his close friends "Catch A Lot" and "Liongator"; scalloping and quahogging in the river (there were always quahogs in the bucket under the boat!). And boy could he dance!
During the day he could always be found with his best friend "Hollywood" (Wayne Sunderland).
Survivors include his 2 daughters: Luanne Medeiros and her husband Joseph of Westport and Susan M. Massey and her fiancé Thomas Cambra of New Bedford; his granddaughter: Judi Medeiros and his step great grandson: Brenden Gray.
He was the longtime companion of the late Cleda Mae Buress and was formerly married to Judith (Collins) O'Loughlin, Carol Seney and Sandra (Choquette) Massey.
Services are private.
In lieu of flowers, memorial donations may be made to A Wish Come True at https://www.awish.org/donate