Leonard Riley
A quietly religious, gentle man who valued family, friends and sports, especially basketball and golf
It is with heavy hearts that we announce the peaceful passing of Leonard (Lenny) Riley at his home in Winthrop on August 12, 2025, at the age of 81, surrounded by his wife, sister and children. Lenny left us with cherished memories and a legacy of love.
Born on July 12, 1944, to the late Leonard Patrick Riley and Catherine (Shea) Riley, Lenny was the beloved husband of Peggy (Cash) Riley for nearly 58 wonderful years. He is survived by his sister, Kathy Riley and her late husband, Darrell Elrod of South Carolina. Lenny was a devoted father to Leonard Riley and his wife, Cheryl of Walpole, Sean Riley and his wife. Sheri, Kathleen Cappuccio and her husband, Gerry, Shannon Poulos and her husband, Jon of Winthrop and Tammy Marino and her husband, Michael of Wilmington. His love and pride extended to his grandchildren: Kevin, Connor, Taylor, Meghan, Dillon, Owen and Luke Riley; Christopher, Nicholas and Arianna Cappuccio; Jonny, Allie and Riley Poulos; and Matthew and Michael Marino. He also leaves behind many wonderful nieces and nephews and he was the dear brother-in-law of Jeanne, Gerry and Mary Ann Cash.
Lenny and Peggy met at Winthrop High School when they were just teenagers and their love story continued as lifelong residents of Winthrop. They married in November 1967 and together they were blessed with five children and 15 grandchildren, a testament to their love and commitment.
Growing up on Cottage Hill, Lenny formed lifelong friendships that he cherished deeply. After graduating from Winthrop High School in 1963, he became an apprentice plumber for Crane Plumbing and Heating and eventually retired from the Boston Globe, where he met some of his earliest and lifelong friends. Lenny had many friends, but he was especially close to Paul, Jimmy, and Dennis, a unique group of four incredibly close friends.
Lenny was a quietly religious, gentle man who valued family, friends, sports, especially basketball and golf. One of his greatest joys was watching his children and grandchildren compete in their sporting events. He was a lifelong member of the Winthrop Yacht Club and Winthrop Golf Club and was known for his outstanding basketball skills in high school. Many would say he was the best basketball player to ever play for Winthrop High School, and he was recommended for the WHS Hall of Fame. In true Lenny fashion, he only accepted the honor when his entire State Championship Team, of which he was Co-captain, would be inducted at the same time. His humility and kindness were truly remarkable.
Lenny’s legacy is one of a good son, brother, husband, father, grandfather, uncle, and friend. In lieu of flowers, donations can be made to The Viking Pride Foundation or St. Jude Children’s Research Hospital.
The funeral was conducted from the Caggiano-O’Maley-Frazier Funeral Home, Winthrop on Monday, August 18, 2025 followed by a funeral mass in St. John the Evangelist Church. Rev Charles Bourke celebrated the mass and offered prayers at the interment in the Belle Isle Cemetery in Winthrop.
“Life is an ocean, and love is a boat, in troubled waters that keeps us afloat.”
To sign the online guestbook, go to www.caggianofuneralhome.com.
Christine Jacques
New England Telephone retiree
Christine A. Jacques of Winthrop passed away at the Leonard Florence Center for Living in Chelsea on August 17, 2025. She was 91 years old.
Born in New Jersey, she was the beloved daughter of the late Beatrice (Barton) and Anthony Sepe. She resided in Winthrop for many years before moving to West Palm Beach, Florida. She resided in West Palm Beach for over 37 years before moving back to Winthrop 15 years ago. Prior to her retirement she worked as a telephone operator for New England Telephone.
She was the devoted wife of the late William Jacques and the loving mother of William Jacques and Lorraine Carroll and her husband, David, all of Winthrop and the late Paul Jacques; dear sister of Maryann Giunta of Florida and the late Joseph Sepe and Barbara Wright. She is also survived by six grandchildren and eight great grandchildren.
Family and friends are cordially invited to attend the visitation from the Caggiano-Maley-Frazier Funeral Home, Winthrop on Saturday, August 23 from 9 to 11 a,m. followed by a funeral mass in St. John the Evangelist Church, 320 Winthrop St., Winthrop at 11:30 a.m. Services will conclude with the interment in the Belle Isle section of Winthrop Cemetery.
To sign the online guestbook, go to www.caggianofuneralhome.com.