BANGOR, Maine -- 01/27/2017 -- Woodrow Cross (center) laughs with Donna Power during the Bangor Region Chamber of Commerce annual dinner at the Cross Insurance Center in Bangor Friday. Cross, a Bangor region volunteer for many years, was honored with the Norbert X. Dowd Award. Ashley L. Conti | BDN

Woodrow Cross, who rose from small town boy to founder of one of the largest business insurance firms in the country, died Sunday at the age of 103.

Cross founded the Cross Insurance Agency in 1954 out of his home in Bangor. More than 60 years later, the company has more than 40 branches and about 1,000 employees spread throughout eight states, according to his obituary. Both of Maine’s largest municipal arenas bear the name of the company — the Cross Insurance Center in Bangor and the Cross Insurance Arena in Portland — and its biggest clients include the New England Patriots, the Boston Red Sox, the Boston Bruins, Cianbro and The Boston Globe.

Cross was born in 1916 on a small farm in the Penobscot County town of Bradford, where his family ran a general store, according to his obituary. An entrepreneur from the earliest age, Cross’ first business venture was selling seeds out of a pony cart at the age of six.

Near the end of the Great Depression, his father died, and 21-year-old Cross became the de facto head of the family, running the store for the next 16 years, only stopping to serve in the Army during World War II, during which he fought in combat against Japan. During the war, in 1943, he married Janette Bean, with whom he would have five children: Dennis, Royce, Connie, Judy, and Brent, a former executive vice president of the company, who died in 2015. Janette died in 1992.

In 1954, Cross sold the general store and moved his family from Bradford to Bangor, to take advantage of the city’s better educational opportunities for their children. Initially, he worked at a mill and on the construction crew that helped build the Bangor Auditorium. He also became licensed to sell insurance, and later that year, launched the Woodrow W. Cross Agency from his kitchen table on West Broadway.

Over the ensuing decades, Cross grew his insurance business, slowly but surely. In 1963, he moved the business from his home to an office in downtown Bangor, and hired his first employee. As more and more employees came on board, in 1970 he hired his first family member: eldest son Royce Cross, who is now president and chief executive officer of the company.

Cross never stopped working, even when he stepped down as president in 1983 and Royce Cross took on that role. In fact, as chairman of the board, Cross came into the office multiple times per week, well into his 90s. The company moved its Bangor headquarters to the corner of Main and Buck streets in 2015, into the former offices for the Bangor Daily News — next door to the arena and conference center that bears its name.

In January 2017, a month after his 100th birthday, Cross received the Norbert X. Dowd Award, given by the Bangor Area Chamber of Commerce for lifetime achievement. Among other honors he received were an honorary Doctorate of Business Administration from Husson University, Junior Achievement Maine Business Hall of Fame, and the Key to the City of Bangor.

At the time of his death he was the oldest member of Calvary Baptist Church in Brewer, where he was a member for 66 years. His family plans to hold a funeral for him in a private graveside service, according to his obituary.

BDN reporter Bill Trotter contributed to this story.

Bill Trotter

A news reporter in coastal Maine for more than 20 years, Bill Trotter writes about how the Atlantic Ocean and the state's iconic coastline help to shape the lives of coastal Maine residents and visitors....