Woodrow Cross, who built his insurance firm into a major New England business, dies at 103

Woodrow Cross
Woodrow CrossHandout

As a 13-year-old in a small Maine town, Woodrow Cross left school after eighth grade to help support his family during the Great Depression.

His father, he often recalled, would tell him: “You have to make work for yourself.”

And so he did. Even as a boy, Mr. Cross found ways to earn money when work was scarce. After his father died, he ran his family’s general store in Bradford, Maine, which they had built with lumber from fallen down buildings, straightening old nails to use again.

In his late 30s, he launched an insurance agency in Bangor and, over the next 66 years, turned a business he had first run from his kitchen table into a firm with more than 900 employees in more than 40 New England locations.


Even after a fall slowed him at 99, Mr. Cross never fully retired. He was 103 when he died in his Bangor residence last Sunday.

Mr. Cross, who sold seeds door-to-door as a boy of 6 and raised chickens to sell when he was a teenager, possessed a legendary work ethic that inspired those who met him as he closed in on the century mark.

“He liked being the one who unlocked the door in the morning and then locked the door at the end of the day,” said his grandson Jonathan Cross, chief operating officer of Cross Insurance.

“People would come in for a business meeting,” Jonathan said. “He was very polite and also had a powerful way of letting people know they had to be on their toes. He would sit at the table, as a man well into his 90s, until the deal was negotiated. If you didn’t plan for enough time, that was your fault. He was going to stay until it was done.”


Among the clients of Cross Insurance are sports teams such as the New England Patriots, the Boston Bruins, and the Boston Red Sox.

Mr. Cross “was a brilliant, hard-working businessman who, in addition to his entrepreneurial success, always understood that nothing is more important than family,” Patriots owner Robert Kraft said in a statement.

Cam Neely, president of the Bruins, said in a statement that Mr. Cross “was a true American success story.”

And Sam Kennedy, the Red Sox president and chief executive, noted in a statement that Mr. Cross “created an insurance empire from scratch, and managed to do it with dignity and integrity.”

Mr. Cross did so with almost no academic training beyond the eighth grade, but with an abundance of real life education.

In middle age, he obtained a general equivalency diploma because he needed one for a real estate license, his grandson said.

At 20, Mr. Cross had attended classes at a school of commerce run by Chesley H. Husson, who founded what is now Husson University in Bangor. The university subsequently awarded an honorary doctorate to Mr. Cross.

The business world was Mr. Cross’s real classroom, though.

At the outset of the Great Depression, barely into adolescence, he would join his father on trips from their home in Bradford north to Aroostook County to fill their truck with potatoes, and then drive south more than 100 miles to sell them for a profit in wealthier places such as Bar Harbor.


“It’s very easy to get discouraged, but I always tried to figure out the problem,” Mr. Cross told the Portland Press Herald in 2017, after he had turned 100. “I didn’t run from it, and if I needed help, I’d get it. And if I needed to do more work, I did it.”

Born on Dec. 29, 1916, Woodrow Cross was the oldest of three siblings and grew up some 20 miles north of Bangor in Bradford, a town of then fewer than 1,000 people.

Through the eighth grade, Mr. Cross attended a one-room schoolhouse, where in colder months he was responsible for filling the wood box to fuel the stove that heated the classroom.

His father, Melvin Cross, and mother, Mabel Speed, ran a farm until the family opened M.W. Cross General Store, not long before Mr. Cross ended his school years.

At 21, Mr. Cross became the store’s proprietor, after his father died. He only left Maine to serve in the Army as a staff sergeant during World War II.

While home on leave, Mr. Cross married Janette Loretta Bean on Sept. 7, 1943, in a ceremony at her family’s home in East Corinth, Maine.

Initially, the Army sent him to boot camp in Texas. Mr. Cross was stationed in Austin and then in Louisiana before being shipped to the Pacific, where he was part of the military campaigns in New Guinea and the Philippines. He also served in Japan as part of the US occupying forces after the war before returning to Maine.


For decades he marched in Bangor’s Memorial Day parade, only agreeing to ride in the procession after he was injured in a fall at age 99.

Mr. Cross and his wife had five children and settled in Bangor, where he started his insurance agency.

She died in 1992 and their son Brent died in 2015.

During her last couple of years, while she was being treated for cancer, “as important as the office was to him, he walked away and took care of her,” Jonathan recalled. “He set the bar incredibly high as far as caring for his wife and making sure she had everything she needed.”

Mr. Cross founded his insurance agency in 1954.

“I thought that might be something I could get interested in,” he said in an Eastern Maine Medical Center “Voices From the Past” interview that is posted online.

Retirement never held any allure.

“I’ve always worked,” he said in an interview when he was in his late 80s and his agency celebrated 50 years in business, in 2004. “I have no interest in going home and watching television.”

Throughout his life, Mr. Cross attended Calvary Baptist Church in Brewer, Maine, across the Penobscot River from Bangor, serving as an usher and church officer. He also was a benefactor of many Maine charities.

“He was the kind of glue that holds a community together,” former Maine Governor John Baldacci told the Bangor Daily News.


In addition to his grandson Jonathan, Mr. Cross leaves two daughters, Connie Guelich of Roanoke, Va., and Judith Cross Olson of Lexington; two sons, Dennis of Orono, Maine, and Royce of Brewer; 13 other grandchildren; 16 great-grandchildren; and a great-great granddaughter.

The family held a memorial service and a graveside military burial service.

For years, even while running his agency, Mr. Cross was so directly involved in the business that he preferred to open the daily mail.

“I’d get the mail, bring it in, and he and I would open it together. It was a special part of the day,” his grandson Woodrow Cross II, who is now vice president of risk management for Cross Insurance, said of his early days with the agency.

“Looking back,” he added, “the time I got to spend with him was invaluable — sitting there, talking about what we had on the agenda for the day, listening to his life lessons.”

Bryan Marquard can be reached at bryan.marquard@globe.com.