It wouldn’t be hard to envision Ron Cain sitting on a wooden bench in a hockey rink, lacing up a pair of skates while talking trash before a men’s league game.

Until a few years ago, that’s exactly where the new majority owner and CEO of the Portland Pirates could be found, playing the game he learned while growing up outside of Boston.

An affable guy with a burly build and a touch of bravado, Cain has become the face of Portland’s American Hockey League franchise since the recent departure of longtime Pirates CEO Brian Petrovek. But the 50-year-old Kennebunk resident prefers to keep a low profile.

“He’s like one of the boys when he comes to the rink,” said Kent Hulst, who played for the Pirates in the 1990s and now works for Cain in Saco as a coach and administrator with the Junior Pirates. “He’s very humble, soft-spoken.”

Cain is a self-made entrepreneur who worked his way up in a blue-collar industry to become chairman and CEO of a supply-chain and logistics business called Legacy Holding, which he expects will gross $383 million this year.

He’s already proven to be a sharp negotiator. Cain helped to break a months-long impasse in negotiations with trustees of the Cumberland County Civic Center that led to a new five-year agreement to keep the team in Portland.


Now he faces another challenge – turning around a franchise coming off a season in which the Pirates finished with the league’s worst record and lowest attendance while playing all their home games in Lewiston.

Still, this much is obvious: There’s nowhere to go but up.

“When he sets his mind to something, he finds a way to get it done,” said Mark Anthoine Sr., a partner with Cain in the Maine Hockey Group, which owns the Junior Pirates. “He surrounds himself with very skilled people and supports those people to help them become successful.”

Cain places an emphasis on community service at Legacy Holding, and vows to do the same with the Pirates.

“I feel very confident that people will see a change within the community and how things are run,” Hulst said.

Associates praise him for his charitable contributions, though Cain is reluctant to offer many details about his philanthropy.


As with his charity work, other details about Cain’s background are difficult to pin down. Information offered on the Pirates’ website and by Cain himself were inconsistent with college records and other documents researched by the Maine Sunday Telegram.


Cain grew up the oldest of four children in Billerica, Massachusetts. His father, Ronald Sr., worked his way up from truck driver to vice president of operations for a grocery wholesaler. So logistics – the movement of product from source material all the way through finished goods and delivery to final use – was dinner-table conversation.

While still in college, Cain found himself supervising Local 170 Teamsters in Worcester, Massachusetts.

“My dad ran the business and I was the kid on the floor,” he said. “You learn real fast how to manage people, how to treat people, when to push and when not to push.”

Brimming with confidence and ambition, Cain approached the owner of a grocery wholesaler in Dracut, just north of Lowell, to apply for director of operations. The owner was skeptical about hiring someone so young. Cain pointed to his experience and offered a proposition.


“I said I’ll work for free until you feel like you can pay me, or that you want to pay me, until I’ve earned the job,” he said. “So the guy brought me in and I worked three weeks for free, and then I got the job.”

Other work in supply-chain management followed, including a three-year stint with the now-defunct Associated Grocers of Maine, based in Gardiner. Cain and his wife, Terry, lived first in Scarborough and then in South Portland and were in the process of starting a family.

“When we left (Maine), we knew it was one of those major life mistakes, that we really didn’t want to leave,” Cain said. “But we took a promotion and ended up back in Massachusetts. From that point on, I was always trying to figure out, OK, what business can I buy into or get back into to get back to Maine?”

The seeds of that opportunity took root in 1999, when John Van Tomme sought a meeting with Cain. Five years earlier, Van Tomme had started his own logistics company called TMSi, based in Florida.

“We met because I heard about Ron in the marketplace,” said Van Tomme, now retired and living in Denver. “Sharp, competitive, a team player, though. Good with his people. People really liked him. I decided he was an important guy to get to know.”

Over dinner at a steakhouse, Van Tomme made a pitch, telling him he’d like to buy a business venture that Cain was planning.


“I hadn’t even named it,” Cain said. “I hadn’t even started anything yet. I said, ‘Well, I want to buy yours.’ Now, I didn’t have two cents. We had no money, had young kids. We were (living) week to week.”

When Van Tomme inquired about Cain’s financial resources, Cain responded with a deal similar to the one that worked in Dracut.

“I said, ‘I don’t have anything, but I’ll guarantee you I’ll bring in $10 million in business within two years. And if I don’t do it, then I’ll give you back the 40 percent,’ ” Cain said. “I ended up doing it within a year, so I got 40 percent of the business by bringing that in.”

Gradually, the company grew and TMSi had become Legacy Holding by the time a Canadian company came into the fold last year, adding an office in Toronto. The core business includes 64 warehouses in the United States and Canada, about 3,700 employees, and does imports and exports with Europe and Asia in addition to its North American supply-chain service.


Cain’s business acumen was honed at a young age. So was his passion for hockey.


“I played a lot of team sports, but hockey is more near and dear because the coaches have more of a direct impact on the kids,” he said. “At least, that’s my perception. My best friends came from the game.”

Hockey, Cain said, taught him how to build a team, how to be a role player, how to be a leader.

During an interview in May, Cain said he played in high school and “a little bit in college.”

When asked where, he said Northeastern University, and reiterated that it was “just a little bit there.”

Cain’s name is absent from Northeastern’s varsity rosters from the 1980s and the school’s sports information office found no mention of his name. In a subsequent phone conversation, Cain spoke of being “hurt most of the time.” Questioned again in a follow-up interview, he cleared up the confusion.

“That’s my fault for leaving that impression,” he said. “At Northeastern I played club hockey, which I think you can refer to as JV. I tried to walk on (to the varsity program), but I just couldn’t do it. I had no scholarship. I had to pay for my own stuff.”


When Cain took over majority control of the Pirates, the team added a brief biography of him on its website. The bio, identical to one found on Legacy’s website, stated that he holds a bachelor’s degree from Northeastern and an executive master of business administration degree from Harvard University.

Harvard Business School does not grant such a degree. Neither it nor Harvard Extension School could find a record of Cain attending. And according to the registrar’s office at Northeastern, Cain enrolled in September 1982 and withdrew in January 1987 without fulfilling requirements for an undergraduate degree.

After Cain was questioned about those inconsistencies, biographies on both sites have been changed to say he attended Northeastern and completed Harvard’s executive management program.

“Those things were purely mistakes,” Cain said. “They were not something that was crafted for a benefit. It wasn’t anything that I did, but it’s my fault that I didn’t recognize it earlier and take it down.”

Rick Dempsey, vice president of marketing for Legacy, said that an outside agency was contracted to write bios of Cain and other Legacy executives and that the agency had pulled information from a variety of sources. Dempsey also said the rush to prepare the bios for the launch of a new website earlier this year may have contributed to the mistakes. He took the blame for not insisting that Legacy execs sign off on their bios.

However, a previous version of the Legacy website, shown on the Internet Archive as being from April 2013, also includes a bio stating that Cain holds a bachelor’s degree from Northeastern and a master’s degree from Harvard Business School.



Cain and his family returned to Maine in 2002, settling in Kennebunk. His oldest son, Cam, became involved with youth hockey and Ron volunteered as a coach. That’s when Ron Cain met Mark Anthoine Sr., a managing partner in an employee benefits, insurance and investment firm with offices in Auburn and Portland.

“I didn’t know Ron other than that he was coaching (my son),” said Anthoine. “There came a time when the Maine Hockey Group, which owns the Portland Junior Pirates, was looking for some financial backing when they were going through some challenging times. Ron and I stepped in as parents trying to help support the program.”

Cain and Anthoine became partners with MHG founders Sean O’Brien and Jay Pecora and eventually took over the program, expanding it from one junior team playing out of a rink in Biddeford to its current roster of 16 youth teams – four of them for girls – and two junior teams, based in both Saco and Lewiston.

Included in that expansion was the MHG Ice Centre in Saco, an old warehouse converted into a hockey rink, training facility and offices for Orthopaedic Associates (which owns 40 percent of the facility to Cain’s 60 percent) and Octagon sports marketers.

In 2010, the owners of the Portland Pirates were looking for more investors and approached Cain with a proposal in which both professional and junior hockey players could share training space in Saco.


Brian Petrovek and Lyman Bullard, college roommates who had played hockey together at Harvard in the mid-1970s, put together an investment group that bought the Pirates in 2000. They quickly took a liking to Cain, first because of his genuine love of the game, said Petrovek, then because of his acumen as a businessman and his commitment to giving back to the community.

“You might think it’s a bunch of marketing speak,” Petrovek said, “but it makes people on his staff come to tears when it comes to the commitment his company makes, in terms of time and treasure, in giving back to the community.”

As an example of “giving back,” the Pirates will be hosting a charity golf tournament Saturday in Old Orchard Beach featuring members of the team’s 1994 Calder Cup Champions. The event will raise money for Camp Sunshine, a Casco-based nonprofit that assists families with children who have life-threatening illnesses.


What initially began as a 40 percent interest in the Portland Pirates for Cain grew to a little more than half by last December. It gives him controlling interest in a franchise that, if the 2011 sale of another AHL franchise is a good barometer, is valued in the neighborhood of $4.5 million.

When the Pirates announced Cain had become the majority owner, the most interested observer may have been Neal Pratt, chairman of the civic center board of trustees, who hoped to end the lengthy impasse between the team and the arena.


“When I read in the paper some pretty conciliatory quotes attributed to Ron,” Pratt said, “I saw them as an opportunity to at least have a cup of coffee to see if their position had changed.”

Turns out Cain was thinking along similar lines. He wrote a letter to Pratt that arrived the day after Pratt placed a call to Cain. Shortly thereafter, they met in Portsmouth in Cain’s office, outside of which is a framed Red Wings jersey autographed by Gordie Howe, who is also known as Mr. Hockey.

“He’s very cordial,” Pratt said of Cain, “very personable.”

The two men hit it off. They talked parameters of the lease proposal. When negotiations had broken down in late summer, about a dozen issues remained in dispute, Pratt said.

Both men clearly wanted a resolution because, as Cain put it, they were dance partners who needed to dance together.

“When you get into any negotiation, it can get emotional,” Cain said. “I don’t care who it’s with, whenever it is. And time needs to pass for that emotion to dissipate. By December, that had happened. I’m not saying I’m better at negotiating than anybody else, but the time had passed and I wasn’t emotional with it. Nor was Neal.”


The day after their conversation over coffee, the Pirates dismissed their lawsuit against the civic center, a significant step that paved the way for a five-year agreement signed in early February that is similar to a proposal the Pirates refused the previous summer.

“When we took a look at the issues again, ours made sense and theirs made sense and it was a give and take,” Cain said. “If you leave a negotiation and everybody’s satisfied – maybe not completely happy, but satisfied – then it’s a good negotiation.”

As a lawyer, Pratt appreciates Cain’s ability to get to the nub of an issue without a lot of wasted time. As a businessman, Pratt appreciates Cain’s accomplishments and the importance he places on community service.

What also became clear was Cain’s passion for hockey.

“I think that’s one of his driving motivations,” Pratt said. “And that’s a good thing. Because people who love the sport want to do the right thing for the sport. That encouraged me in my dealings with him.”

“He’s certainly a good businessman, but he’s in it for more than the money, as far as I can tell. He’s not just an owner, he’s a fan.”

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