John Leonard looked across a sales contest in New York and saw a casting problem. He and John Marr, MEMIC’s senior vice president of claims, were competing against younger executives with an elaborate technology presentation. Leonard thought of Space Cowboys, the film in which veteran aviators find themselves up against a younger generation. “Do I look that old?” he wondered. It was a reasonable question for someone trying to sell experience in a room full of presentation equipment.
When their turn arrived, Leonard and Marr talked about the company’s record and the work they knew. A board member subsequently said he felt comfortable with them and believed he could trust them. MEMIC won the contract. Leonard had found a useful role for the older cast members.
The episode catches something about John T. Leonard: an executive willing to laugh at himself, but quite serious about what a customer was buying. He spent much of his career in a business that asks people to pay now for a promise that will matter later. Earning confidence was part of the product.
A company already waiting for its president
MEMIC’s origin requires a small correction to the usual founder story. Leonard did not dream up an insurer and then persuade Maine to make room for it. Maine’s legislature passed reforms in 1992 that created the framework for a private mutual insurance company. A board of incorporators did the work of establishing it. The company wrote its first policy on January 1, 1993. Leonard was hired that February.
That distinction makes his assignment more interesting. There was already a public purpose, a governing structure and an urgent demand for coverage. What remained was the daily work of turning those things into an institution people would choose to deal with. A statute could establish the company. It could hardly answer every customer’s question.
Maine’s insurance market had been coming apart. Employers faced expensive workers’ compensation coverage, and carriers were withdrawing. MEMIC became the guaranteed market for employers who needed that insurance. The new president therefore arrived at a business with customers waiting, rather than a business waiting for customers. In its early months, thousands of employers came aboard.
There was a financial complication. The company received neither state funding nor a state guarantee. Its initial resources included a $500,000 line of credit. The public had an interest in its success; the public treasury was not its starting balance.
Borrowing capacity at the start and assets near retirement are different measures. Together, they show how much institution-building lay between the two dates.
The scholarship came first
Leonard had experience with an opportunity arriving before the resources to pursue it. In September 1960, a scholarship took him to Siena College. He would become the first person in his family to earn a college degree. Years later, he credited the liberal arts education with teaching him to think critically and communicate with employees, clients and other stakeholders.
Insurance offers plenty of occasions to discover whether those skills are real. A policy can be technically sound and still leave its buyer bewildered. A business can be financially disciplined and still fail to explain why anyone should trust it. Leonard’s account of his education put thinking and communication together, which is a useful arrangement for an executive who must make promises understandable.
He graduated with Siena’s class of 1964 and joined Travelers. His career there lasted 27 years; he eventually led its commercial lines agency marketing and underwriting division. Before the small Maine company, then, came a long apprenticeship inside an established national insurer. He brought knowledge of both selling insurance and deciding which risks a company could carry.
That history also changes the picture of his 1993 move. MEMIC was a new enterprise led by someone who had already spent decades learning the trade. The second act came with a line of credit and considerable experience.
Making the mutual part matter
As a mutual company, MEMIC belonged to its policyholders. That gave the relationship between insurer and customer a financial dimension beyond the annual premium. When results and capital permitted, money could go back to the businesses that had helped build the company.
Early policyholders paid a capitalization fee. MEMIC had been allowed ten years to build adequate capital; it stopped collecting the fee after five, having collected $47 million. In 1998, it began returning that capital to eligible policyholders. Annual dividends followed in 2001. The sequence matters: customers helped finance the institution before sharing in its financial success.
By the December 2016 announcement of Leonard’s retirement, MEMIC reported more than $220 million returned to policyholders since 1998 and a surplus exceeding $400 million. Those were company figures accumulated over years, rather than a single dramatic transaction. They describe a patient kind of growth, built around renewals, reserves and repeated dealings with the same customers.
Leonard took the idea further. Looking toward retirement, he imagined dividends eventually offsetting the cost of coverage for Maine employers. It was an aspiration, not an accomplished result. Still, it reveals the direction of his thinking: success would become especially persuasive when a customer could see it in the arithmetic of running a business.
“The establishment and success of MEMIC has been a labor of love.”
John T. Leonard, December 2016
Experience travels
The company’s Maine beginnings did not keep Leonard’s ambitions inside the state. In 2000, MEMIC formed a New Hampshire subsidiary, MEMIC Indemnity Company. A second subsidiary followed through a 2012 acquisition. By the time he announced his departure, the group wrote more workers’ compensation premium outside Maine than inside it.
The geography was changing while the specialty remained familiar. Offices extended down the East Coast. Leonard was taking an insurance business developed in one particular market into places where its reputation had to be earned again. The New York sales encounter with Marr belongs in that larger story: experience could open a conversation, but the next customer still had to be convinced.
His industry work also carried him beyond MEMIC. He chaired ACORD, the organization concerned with insurance data standards, in 2001 and again in 2008. In 2010, he became chair of the National Council on Compensation Insurance, after serving on its board in the 1990s and returning in 2007. Running one carrier and working on the industry’s shared machinery were parallel parts of his career.
Those appointments involved the less theatrical side of business influence: committees, standards and the information on which insurance decisions depend. A memorable sales pitch might win a contract. Much of an insurance executive’s working life proceeds without an audience.
Leaving someone ready to take over
Leonard announced his retirement in December 2016, giving the board time to choose a successor. Its search considered internal and external candidates. In May 2017, the company announced that Michael Bourque would take the job. Nearly 400 employees gathered for the announcement.
Bourque had joined MEMIC in 1995 as a communications specialist and worked his way through management roles to senior vice president of external affairs. He had spent almost 22 years inside the company when he was selected. The next chief executive had learned the business alongside the first.
Leonard emphasized integrity and the ability to give other people confidence when discussing what mattered in a successor. Bourque, in turn, spoke of the mentorship he had received and the importance of continuing that practice. There is a practical test hidden in those remarks. An organization that has learned from its leader should eventually have people capable of leading it.
Bourque became president and CEO in September 2017. Leonard’s retirement therefore had an observable outcome beyond a farewell: responsibility moved to someone who had developed within the institution over two decades. The company’s story acquired another principal character.
A different sort of retirement present
MEMIC’s board chose education as a way to recognize its departing leader. In August 2017, the University of Southern Maine announced the MEMIC John T. Leonard Endowed Chair in Risk Management and Insurance. The company committed $1.5 million over five years and sought matching gifts toward a $3 million endowment.
The arrangement had a business purpose as well as a commemorative one. USM’s risk management and insurance program had begun in 2008 with industry collaboration, including MEMIC. By 2017, its graduates had found work at roughly 40 insurance organizations, including positions at MEMIC. Expanding the program meant preparing people for work the region already needed done.
Leonard had made a related decision at Siena. For his 50th reunion, he arranged an estate gift to endow a scholarship. “It was just natural to ‘pay it forward’ as someone had done for me,” he said. The student who had received help in 1960 had kept the transaction in mind for half a century.
On October 17, 2018, the Maine State Chamber honored him with its Alton “Chuck” Cianchette Business Hall of Fame Award. The recognition joined a career that had reached into insurance organizations and Maine’s educational institutions. An award offers a moment at a lectern; a funded scholarship or teaching position has a longer working schedule.
Seven continents, one familiar hotel preference
Retirement took Leonard to Sarasota, Florida. He continued serving on corporate boards and investing, while making room for travel. He visited all seven continents and estimated that he spent more than 90 days a year at sea. His family also remembered his fondness for a good Marriott, a pleasingly specific preference for someone with such a large travel map.
There were sporting loyalties, too: the Patriots and Celtics, with an enduring affection for the New York Giants. He invested in the Maine Red Claws and took grandchildren to Sea Dogs games. He completed two New York City marathons. The person behind the insurance titles had found several ways to spend an afternoon without discussing underwriting.
Leonard died on November 3, 2025, aged 82. His life connected an Albany childhood, a scholarship in New York, a long career at Travelers and nearly a quarter century building MEMIC. The scholarship he funded and the chair bearing his name give that history a continuing use. Someone else can enter a classroom, learn the trade, and eventually take a turn across the table.