Richard Gershon Lesser, 91, of Jupiter, Fla., and Martha’s Vineyard, passed away peacefully at home, surrounded by his beloved family, on August 13, 2026. Dick lived a full life defined by family, hard work, generosity, and an extraordinary capacity for making people feel valued.

Dick was born on Nov. 14, 1934, and grew up in Newton. He was the son of loving parents Charlotte and David Lesser, and the younger brother of Adison Lesser. He attended Northeastern University, where the work ethic that would characterize his entire life was already apparent: While in college, he worked three jobs to help support his family.

That determination led to a long and enormously successful career in retail. He began his career at Zayre and Filene’s, was a co-founder of Reebok USA, and eventually joined the company that would become his beloved professional home, TJX. He quickly rose through its ranks, ultimately becoming president of TJX. As proud as Dick was of the company’s success, he was equally proud of its people. He believed deeply in treating people with respect, and helped build a culture around that belief that endures today. He was an admired boss and mentor to many.

Dick brought the same energy to the rest of his life. He was an avid and remarkably dedicated exerciser who loved golf, walking, and water aerobics. He was a voracious reader and student of history, with a particular fascination with World War II, Harry Truman, and Winston Churchill. He was also an undaunted lifelong Red Sox fan.

Accomplishments, books, golf, and even his beloved TJX came second to what mattered most to Richard: his family. He took enormous pride in his daughters, Susan and Liz, and loved his sons-in-law, grandchildren, and great-grandchildren deeply. Nothing gave him greater pleasure than being surrounded by the people he loved and watching his family grow and thrive.

That circle of love extended far beyond his immediate family. Richard treasured his nieces and nephews, extended family, and his many friends. He had an extraordinary ability to make people feel confident, cared for, and valued, and the friendships he formed throughout his life meant a great deal to him.

He was exceptionally generous, not only with the people he loved but with anyone he believed needed help. Philanthropy was important to him because he believed that those who were fortunate had an obligation to help others. He was particularly supportive of Alzheimer’s research, Martha’s Vineyard Hospital, Jupiter Medical Center, and Jewish philanthropies. 

At the center of Richard’s life was Clare. He fell madly in love with her from the moment they met. They were engaged 10 days later, and married within three months. What might have seemed impossibly impulsive to anyone else became a 63-year love affair. Through all the accomplishments and adventures of his life, Clare remained the person he loved most, and his everything.

Richard was warm and affectionate, wise and reassuring. He worked hard, loved deeply, and gave generously. Above all, he measured the richness of his life in the people he loved and who loved him in return.

He is survived by his wife, Clare Lesser; his daughters, Susan Alpert and Liz Chroman; his sons-in-law, Joseph Alpert and Jason Chroman; his beloved grandchildren, Rachel Alpert Freydberg (husband Jason Freydberg), Matthew Alpert (wife Taylor Alpert), Katherine Alpert, Michael Alpert, Zachary Chroman, and Cole Chroman; and his two great-granddaughters, Charlie Alpert and Sophie Freydberg.

Funeral services were held on August 17 at Temple Judea in Palm Beach Gardens, Fla.

A second service will be held on Friday, August 21, at 11 am at the Martha’s Vineyard Hebrew Center in Vineyard Haven.

In lieu of flowers, donations in Richard’s memory may be made to the Jupiter Medical Center Foundation, online at jmcfoundation.org, to Martha’s Vineyard Hospital, online at massgeneralbrigham.org, or the Admirals Cove Foundation, online at admiralscovefoundation.org/give.