Mainers from around the state remembered Cross Insurance founder Woodrow Cross as someone who was dedicated to his community, his employees and his family, and as a self-made man who founded what has become one of the largest business insurance firms in the country.
Former Maine Gov. John Baldacci, a longtime family friend, said that even though the company grew from the family’s kitchen table in its early years to now include more than 40 branches and 1,000 employees in eight states, the Cross family ethic remains firmly in place.
“It’s really those basics of treating people the way you want to be treated, and giving people an honest deal, and the best deal possible,” Baldacci said. “He was the kind of glue that holds a community together.”
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In a Sunday statement, U.S. Sen. Susan Collins praised Cross’ worth ethic and commitment to service.
“For nearly a century, Woodrow Cross’ career as a Maine businessman was defined by his tremendous work ethic, dedication, and integrity,” she said. “Woodrow leaves behind a powerful legacy of service and business leadership.”
Alice Dyer, vice president of operations for Cross Insurance, began her career with the company 35 years ago, when Cross hired her as a bookkeeper. She was the company’s 13th employee.
“I remember to this day how impressed I was with him and his business,” she said. “He made insurance sound exciting, and the possibilities endless. Over the course of the next few years and decades, he became my greatest mentor. He constantly amazed me with his tenacity and passion and commitment.”
Cross’ grandson, chief operating officer Jonathan Cross, has worked in the family business for 25 years. He said his grandfather was keenly aware of the need to provide for everyone — be they family members or employees.
“He spent so much time putting everybody else first. I think he had a lot of responsibility as a very young man, taking over the family business at 21, losing his father at such a young age, and ultimately serving in World War II,” the younger Cross said. “He always wanted to make sure that those around him had the opportunity to be successful.”
Jonathan Cross said that even though his grandfather did not have access to higher education as a young man — though he did eventually attend Husson University — he had an instinctive business sense, and was an excellent judge of character.
“I hear story after story from people that maybe didn’t have the strongest resume or background that would make sense for the job they wanted. But he always trusted the character of people, and would give them opportunities to grow and make their own careers,” he said.
Woodrow Cross retired as president in 1983, but did not stop coming into the office regularly until he was 99. Baldacci said Cross’ son, current president and CEO Royce Cross, took great joy in watching his father continue to work.
“He said that when his father retired, he really just started coming in a little bit later,” Baldacci said. “[Woodrow] came in at 9:30, instead of 8:30. It is hard to be both a good person and to run a good business, but he was able to do both.”
In 2017, when Woodrow Cross was awarded the Norbert X. Dowd Award by the Bangor Region Chamber of Commerce just one month after his 100th birthday, the audience at the ceremony was filled with former employees, said Deb Neuman, the chamber’s executive director.
“It was clear from speaking to them that the impact he had on their lives went far beyond providing them with a job,” Neuman said. “His humble and generous nature was evident when he stood up from his wheelchair to accept the award so he could properly thank everyone who came to honor him.”
Jonathan Cross said his grandfather was a quiet man who preferred to relish in other people’s success and happiness — especially among his family, including his five children, 14 grandchildren, 16 great-grandchildren and one great-great-granddaughter.
“He made time for everybody in the family, whether they were in the business or not,” he said. “He always believed that if you didn’t have a strong family, all your success in business didn’t matter.”
Dyer said that Woodrow Cross’ office at the company headquarters at 491 Main St. was right next door to hers, and the last time he came into the office was about nine months ago, when he was 102.
“I can’t help but glance into his office and see if he’s there, opening the day’s mail,” Dyer said.