Alan Weissman—a devoted father, husband, grandfather, great-grandfather, and friend—passed into eternal rest on February 22, 2026, following a courageous battle with cancer. Known to all as a Scrabble mastermind, a dedicated runner, a college basketball enthusiast, and a jokester, Alan leaves behind a remarkable legacy.

Born on September 16, 1931, in Stamford, CT, to the late Solomon and Elizabeth Weissman, Alan’s life was defined by service and kindness. After earning his bachelor’s degree from UConn, he served his country in the Army while stationed in Japan. Upon his return, he completed a master’s degree in Business at the University of Pittsburgh and launched a successful career in retail merchandising.

It was during this time that Alan met the love of his life, Alicia. Together, they raised their daughters, Sheri and Susan, in New England. An athlete at heart, Alan took up running and continued the pursuit for over 45 years. In 1993, he and Alicia built their dream home in Cape Coral, FL, creating a sanctuary where they hosted cherished memories with their children and grandchildren. The couple also shared a passion for cruising, exploring the world’s most beautiful destinations while forging lifelong friendships along the way.

Following Alicia’s passing at age 63, Alan found strength and community at Temple Beth Shalom. He became an active member of the congregation, dedicating his time to charitable auctions and volunteer work. In his retirement, Alan embraced his passions fully: he was a regular at the Turkey Trot, where he frequently took home the "Oldest Runner" award and often placed first in his age group. Whether he was swimming, traveling, or dominating a Scrabble board, Alan truly remained forever young.

In his later years, Alan was blessed with four great-grandchildren, who became the joys of his world. To Alan, family time was sacred, and he was a steady, joyful heart to all.

Alan is survived by his daughters, Sheri (Bruce) Montgomery and Susan Simmons; his grandchildren, Scott (Hilda) Montgomery, Sarah Montgomery, Kevin Simmons, and Ashley (Chris) Dreher; and his adored great-grandchildren, Debbie, Ryan, Eli, and Hayden. He also leaves behind many beloved nephews and extended family members. He was predeceased by his parents; his beautiful wife, Alicia; his sister, Barbara Kahn; and his son-in-law, Bradley Simmons.

A virtual memorial will be held at 5:30PM on March 17, 2026, for friends and family. In Alan’s memory, donations can be made to the American Cancer Society, the Fort Myers Track Club, or Temple Beth Shalom.

Psalm 23

The Lord is my shepherd; I shall not want. He makes me lie down in green pastures. He leads me beside still waters. He restores my soul. He leads me in paths of righteousness for his name’s sake. Even though I walk through the valley of the shadow of death, I will fear no evil, for you are with me; your rod and your staff, they comfort me. You prepare a table before me in the presence of my enemies; you anoint my head with oil; my cup overflows. Surely goodness and mercy shall follow me all the days of my life, and I shall dwell in the house of the Lord forever.

Memorial Details

Alan Weissman's Memorial ServiceMar 17, 2026 05:30 PM Eastern Time (US and Canada)

Join Zoom Meeting:

https://us06web.zoom.us/j/83728659862

Meeting ID: 837 2865 9862

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