Woodrow Cross, insurance icon, World War II veteran and family man, dies at 103

By Sean Gonsalves & George K. Regan, Jr.

Posted in Press Coverage

Woodrow Cross, legendary entrepreneur, philanthropist and founder of Cross Insurance, died on July 26, 2020 peacefully at the age of 103 surrounded by his family in his hometown of Bangor, Maine.

Cross built Cross Insurance into the largest independent insurance agency in New England, and one of the largest in the nation.

Born on December 1916 and raised on a small farm in Bradford, Maine, Woodrow’s entrepreneurial spirit was evident at an early age when he began selling seeds door to door at six years-old, and later purchased and sold chickens. He attended a one room schoolhouse, but spent most of his time working in his father Melvin Cross’ general store.

The responsibilities of running a business and caring for his family were thrust upon him after his father’s sudden death when Woodrow was just 21. He took charge of the family’s general store as the country fell into the Great Depression. Woodrow managed to keep the store open throughout even as he often extended credit for groceries to struggling families knowing that he likely would not be repaid.

“People were important to him,” daughter Connie Guelich says. “He understood that there were children in those homes, and he did not want them to go hungry.”

It was his experience running the family’s general store that provided him with a business education, having attended formal school only until the eighth grade. When he was 20, Woodrow took classes at
a commerce school run by Chesley H. Husson, founder of what is now Husson University in Bangor. He would later obtain a general equivalency diploma, which he needed to get a real estate license.

In September of 1943, he married a long time family friend, Janette Loretta Bean, at Janette’s family homestead in East Corinth, Maine while Woodrow was on furlough from the U.S. Army before being deployed to the Pacific. Woodrow spent the next three years fighting against Imperial Japan in New Guinea,the Philippines and occupied Japan.

Upon his return from the war, he and Janette settled in Bradford, Maine, where Woodrow resumed managing the family’s general store and started a family.

“As a child, once every winter on a cold, snowy afternoon, he would pull out his Army things, souvenirs from WWII and we’d all sit around the floor and he’d regale us with his stories about the Army,” remembers Connie. “It was all much romanticized at the time, but later in life, he began to open up and unearth those memories about the cost of war, the friends he’d lost and trying to understand why he survived while others did not.”

Always proud of his service, he marched in the Memorial Day Parade in Bangor every year until he was 98. Only after suffering a fall,did he decide to travel the parade route by Jeep until he was 100 years old.

In the early 1950’s, Woodrow moved his family to Bangor where he was determined to start a new business selling insurance. He tried to buy an insurance company before deciding to build his own,starting from his kitchen table in 1954. His kitchen table insurance office is where he worked for the next nine years, until hiring his first employee and moving the business into a downtown Bangor office.

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. The family business has now grown to more than 800 employees in 42 locations across five states.

The Cross brand is now one of the most recognizable in New England, especially in major sporting arenas where Cross Insurance has positioned itself as the official insurance provider for the New England Patriots, Boston Red Sox, and Boston Bruins.

Upon learning of Mr. Cross’ passing, New England Patriots owner Robert Kraft said: “Woodrow Cross was the quintessential American success story. He was a brilliant, hard-working businessman who, in addition to his entrepreneurial success, always understood that nothing is more important than family. It is an honor for our family and our businesses to be so strongly connected to Woodrow’s family and their family business.”

Boston Red Sox President and CEO Sam Kennedy echoed Kraft’s sentiments: “Woodrow Cross’s life exemplified the American dream in every way. He created an insurance empire from scratch and managed to do it with dignity and integrity. I am proud to have his name as part of our family of Red Sox partners.”

Boston Bruins President Cam Neely also praised Woodrow as a “a true American success story.”
“The Boston Bruins are proud to partner with the company that he built and bears the Cross Name,” Neely said.

A long time supporter of countless Maine charities, Woodrow was the recipient of numerous awards and special recognitions including an honorary Doctorate of Business Administration from Husson College, 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.

Woodrow was also an active member of his local church -- Calvary Baptist Church in Brewer,Maine --where he faithfully attended with his family, served as treasurer and usher,and was a regular of the church’s Men’s Bible Study.

“He loved reciting the hymns of the faith,” remembers Minister Andy Spohrer, Woodrow’s former pastor at the Calvary Baptist Church.“He would refer to hymns frequently when I visited him and he practiced what he believed and what he sang.”

He was the loving husband of Janette Bean Cross, his wife of 48 years before her passing in 1992. He is also predeceased by his son Brent Cross of Bangor, Maine, father Melvin Cross and mother Mabel Speed Cross, brother Leon Cross and sister Lulu 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, Maine and Royce Cross (Louise) of Brewer, and daughter-in-law, Lori Cross of Bangor, Maine.His son Brent predeceased him in 2015.

Mr.Cross was also blessed with 14 grandchildren and 16 great grandchildren and one great-great grand-daughter.