Woodrow Cross, a businessman who got his start selling seeds door-to-door as a child and went on to found Cross Insurance, died Sunday. He was 103.

Over six decades, Cross built his company into the largest independent insurance agency in New England and one of the largest in the country. He remained active with the day-to-day operations of the company even after his 100th birthday. His obituary said he died surrounded by his family near his hometown of Bangor.

“For nearly a century, Woodrow Cross’ career as a Maine businessman was defined by his tremendous work ethic, dedication and integrity,” Sen. Susan Collins said in a statement. “… Woodrow has always been a shining example of entrepreneurship and perseverance.”

Cross was remembered by his family on Monday as a humble and hard-working businessman who dedicated his life to his company, family and community.

His grandson, Jonathan Cross, executive vice president and chief operating officer of Cross Insurance, described him as genuine, caring and thoughtful. He said one of the keys to his grandfather’s success was his priority on customer service.

“For his whole life, he would always tell everyone to take good care of the customer,” his grandson recalled. “In business, that’s a common thing to say, but he really lived it. Since the very early days of the agency, he would say, ‘Don’t worry about yourself. Take care of the customer and everything will work out.’ He did that over and over again. That’s the culture he created throughout the organization.”


Cross started his insurance company at his kitchen table, and ran it from there for nine years before hiring employees and moving to downtown Bangor. Cross Insurance now has 1,000 employees in more than 40 locations across eight states. In 2019, the company was named the sixth largest insurance broker in Massachusetts.

His son, Royce Cross of Brewer, is president and chief executive officer of the company. Grandson Woodrow Cross II also works for the company. Another son, Brent Cross, former executive vice president of the company, died in November of 2015 after a battle with cancer.

Jonathan Cross reflected on the two-plus decades he worked alongside his grandfather.

“He had a very special way of letting you know that everything would be OK,” Cross said. “It was: ‘Here’s the problem. Let’s look at it. Let’s talk about it. Let’s think about it. If you make a good solid, ethical and moral decision, then it will all work out.’

“He had this vision and ability to look at something and say this is the direction we need to go in. It was always a hand on your back, not a hand in your face. He would let you know it would be OK if you kept working at it.  He had a very gentle nature. People really wanted to work hard for him and still do.”

Woodrow Cross grew up on a farm in the small Penobscot County town of Bradford, where he went to school in a one-room schoolhouse and his father ran a general store. At age 6, he began selling seeds door-to-door and within four years had moved into chicken farming. He began taking out small loans to purchase baby chicks, which he sold at a profit when they matured, which allowed him to repay his creditors and grow the enterprise.


Cross began working in his father’s general store as a teenager, which strengthened his work ethic and family values, he said in a 2017 interview with the Press Herald.

Cross’ father died during the Great Depression when Cross was 21. He took over the responsibility of running the store and caring for his family. He said the challenge of keeping the business vital during such a difficult economic period had an impact on him that would last a lifetime.

“It’s very easy to get discouraged, but I always tried to figure out the problem. 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,” Cross said in 2017.

When the U.S. entered World War II, Cross enlisted in the Army, serving in the Pacific theater during campaigns in New Guinea and the Philippines. He also served in Japan after the war on occupation duty. He earned two battle stars.

“He was incredibly proud of his time serving the country,” his grandson said. “As much as he accomplished in business, he still had that much more pride for being able to serve his country. He instilled that pride in many, many people.”

He was the loving husband of Janette Cross for 48 years. In 1954, the couple settled in Bangor, where they raised five children. His wife died in 1992.


As he grew his business, Cross was anchored by his family and his faith, his family wrote in his obituary. He had been a member of the Calvary Baptist Church in Brewer since 1954 and was the oldest member at the time of his death. He served the church as treasurer and usher and attended weekly men’s Bible classes.

Cross was a longtime supporter of many Maine charities, his obituary said. He received numerous special awards and honors, including an honorary doctorate of business administration from Husson University and the Norbert X. Dowd Award from the Bangor Chamber of Commerce in 2017.

“Mentoring new hires of all ages, supporting professional growth and encouraging community involvement have always been his business practice,” the Bangor Chamber of Commerce said in its award notice. “A strong work ethic, integrity, business acumen, perseverance and professionalism are but a few of the strengths we most admire in him.”

The company sponsors the Cross Insurance Center in Bangor and Cross Insurance Arena in Portland.

Asked three years ago for the secret to his longevity and how he has been able to remain so active for a century, Cross displayed his characteristic humility and matter-of-fact attitude.

“I just fell into it I guess,” he said. “I always liked my vegetables.”


Jonathan Cross chuckled Monday about his grandfather’s longevity and his strict diet of turkey sandwiches on white bread and M&M’s.

“He was always known for having candy at his desk,” Cross said. “If you had a meeting with him, you were eating candy. He had sweet tooth for sure.”

Woodrow Cross is survived by his two daughters, two sons, 14 grandchildren, 16 great-grandchildren and one great-great-granddaughter.

A private service will be held for his family.


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