Leonard Smith, Local Businessman, Passes Away at 88

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Local Businessman and Restaurateur Leonard Smith, co-founder of Lenny’s Deli, passed away Friday Oct. 18, 2019.  He was 88 years old.

Smith was born on March 25, 1931 to Harry and Anna Smith, as one of their four children.  Growing up, he attended School 59 and later graduated from Baltimore City College. In 1952, he married Ilene Cohen, remaining with her for 31 years until her passing at the age of 48 in 1983. He had two sons, Harris (Jill) and Alan (Amie) Smith, a daughter, Sharon (Stephen) Freiman, 11 grandchildren, and three great grandchildren.


From his teenage years, Smith had a reputation as a hard worker, eventually running a store called Len’s Variety. The establishment sold penny candy, popcorn and snowballs, though it would come to face stiff competition from the 7-Eleven convenience store chain. He also sold insurance as a side job, leading to full-time employment with People’s Life Insurance. On his days “off,” he continued to work at Frankfort Grocery. Eventually, he would spend 20 years working for Gladding Chevrolet as a finance and insurance manager.

In 1985, along with his son Alan, he co-founded Lenny’s Deli, finding a way to open the business just five months after the initial inspiration. While his son focused on managing the business side of the deli, Smith became the public face of the company, with his face decorating everything from drinking cups to the signage. His reputation for hard work continued in the new enterprise, and was said to always be the first one to arrive for work in the morning, mingling with the customers and creating a sense that the deli was a gathering place for the community.

In 1988, he married Carolyn Moscoe, becoming a surrogate father to her sons Jason (Debbie) and Michael (Jeanie) Glasser.

Smith retired to Florida at the age of 70, but returned 12 years later to be closer to his family. He would spend much of his time at his old delicatessen, drinking coffee and “solving the world’s problems in 20 minutes,” according to his son Alan.

Smith was said to be an enthusiastic sports fan, following teams like the Colts, Ravens, Orioles, and local men’s and women’s basketball teams.

Smith’s family considered him a devoted father and grandfather, enjoying family sporting events, plays, b’nai mitzvah, weddings and graduations. Not long before his passing, he was in California for the wedding of a grandson. “He was a wonderful father and grandfather, but most importantly, he was a wonderful man,” said son Alan Smith.

Smith was predeceased by his parents and three siblings.

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