Woodrow Cross, Founder of Cross Insurance, Dies at Age 103

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Woodrow Cross died peacefully on July 26, 2020, at the age of 103 surrounded by his family near his hometown of Bangor, Maine.

He was born more than a century ago in December 1916 on a small farm in Bradford, Maine. Woodrow’s entrepreneurial spirit was apparent at an early age when he sold seeds door to door to other farmers at the tender age of six. As a teenager he raised and sold chickens. He could remember his hometown before electricity, the first telephone, or paved roads were introduced to the area. He attended a one room schoolhouse and spent time as a young man working in his father’s general store.

Woodrow’s grandfather fought in the Civil War and military service was always important to him. His turn came when the US entered WWII. He served in the United States Army and was deployed to the Pacific where he spent three years fighting against Imperial Japan in campaigns in New Guinea and the Philippines, and later performed occupation duty in a defeated Japan. Throughout his life he remained proud of his country and his military service. He enjoyed marching in the Memorial Day Parade in Bangor for many years including 2017 when he was 100 years old.

In September 1943, during the war, Woodrow married his sweetheart, Janette Bean, of East Corinth, Maine. After the war ended, Woodrow and Janette settled down in Bradford where they operated the general store begun by Woodrow’s father in 1929. And, they began to raise a family.
In 1954, Woodrow moved his young family to Bangor where he was determined to start a new business selling insurance. He started the company at his kitchen table, and worked from home for the next nine years, until he hired his first employee and moved from his home to an office in downtown Bangor.

Woodrow’s life was marked by his strong work ethic. In the early days of Cross Insurance, he worked nights building the “old” Bangor Auditorium where it was his job to keep the salamander heaters going to be certain the new concrete set properly. Decades later, when that auditorium was torn down, it was replaced by a new building with his name on it.

Woodrow had a true love for his work. He built Cross Insurance into the largest independent insurance agency in New England and one of the largest in the nation. As a businessman, he prided himself on running a large agency that prioritized customer service. He was also quick to adapt to new technologies and industry automation and relished going to work every day with his sons Royce and the late Brent Cross and grandsons Jonathan and Woodrow II. The family business has now grown to 1,000 employees in over 40 locations across eight states.

Woodrow was a longtime supporter of countless Maine charities and was the recipient of several awards and special recognitions including an honorary Doctorate of Business Administration from Husson University, Junior Achievement Maine Business Hall of Fame, the Key to the City of Bangor, and the prestigious Norbert X. Dowd Award from the Bangor Chamber of Commerce.

As his business grew, he remained anchored by his family and his faith. At the time of his death he was the oldest member of Calvary Baptist Church in Brewer where he was a member since 1954. Woodrow served his church as the treasurer and an usher, and for many years he enjoyed attending a weekly men’s Bible class.

He was the loving husband of Janette Bean Cross, his wife of 48 years before her passing in 1992. He was also predeceased by his son Brent Cross of Bangor, father Melvin Cross and mother Mabel Speed Cross, brother Leon Cross and sister Lula Cross Zinni.

Woodrow Cross’s survivors include daughters Connie Cross Guelich (David) of Roanoke, Virginia, Judith Cross Olson (Greg) of Lexington, Massachusetts, and sons Dennis Cross (Carol) of Orono, Royce Cross (Louise) of Brewer, and daughter-in law, Lori Cross of Bangor. His son Brent predeceased him in 2015. Woodrow was blessed with 14 grandchildren and 16 great grandchildren and one great-great granddaughter.