On Harold Cohen’s first day as a lawyer, he lost eight cases for an insurance company in Boston Municipal Court.

“He ended the day telling them he was going to go back to driving a cab,’’ said Bob Kalis, who knew Mr. Cohen for more than 50 years and had been his law partner.

Rather than cruise the streets of Boston looking for fares, however, Mr. Cohen kept practicing law in the Boston area for the next 60 years.

Mr. Cohen, who lived in Sharon for more than 40 years, died of congestive heart failure April 6 in the Orchard Cove retirement community in Canton. He was 88 and also formerly lived in Foxborough.

In the early 1960s, Mr. Cohen became a partner at Iddings, Kalis, and Cohen in Foxborough, where he worked until 1974. He handled mostly criminal and accident cases and worked with the New England Patriots’ former owner, Billy Sullivan, when he sold the football team.

Mr. Cohen’s partners said he was a rainmaker at the firm because he brought in business and gained the trust of clients.

“Harold was a very personable guy,’’ Kalis said. “Everyone loved Harold … and they liked to be with him.’’

Mr. Cohen was born and grew up in Dorchester. He graduated from Dorchester High School before joining the Navy in 1942.

His family said his goal was to fly planes, and in 1944 he earned his pilot wings.

“He was a crazy kid, and that just went with the territory,’’ said his brother Irwin of North Easton. “He used to jump off bridges… . It was a natural thing.’’

Piloting a PBY amphibious plane, Mr. Cohen was assigned to air rescue work during World War II and the Korean War.

At one point he served with Red Sox slugger Ted Williams during the Korean War and was proud of a photo he kept of the two of them together in their uniforms. By the end of his service, Mr. Cohen had risen to the rank of lieutenant junior grade.