Of the three main figures in Thursday’s shakeup with the Calgary Flames, the man people are talking about the least may actually have the most intriguing past and brightest future.

When president of hockey operations Brian Burke opted to relieve GM Jay Feaster and his assistant John Weisbrod of their duties, talk predictably focused on the known entities with the bigger offices, Burke and Feaster. But speak to anybody who’s worked with Weisbrod and you quickly get a sense he won’t be in the unemployment line long. In fact, Weisbrod is among the candidates the Buffalo Sabres have at least considered for their vacant GM job.

As far as we know, not even The Most Interesting Man in the World can say his career has included building a Stanley Cup winner as well as trading Tracy McGrady and drafting Dwight Howard. But Weisbrod’s diverse background in pro sports includes a 14-month stint as GM of the NBA’s Orlando Magic, where he both dealt McGrady to the Houston Rockets—and received a death threat for his trouble—and ignored conventional wisdom in making the shrewd decision to select Howard out of high school in the 2004 NBA Draft.

“This is the most interesting guy who nobody knows,” said an NHL executive, who was effusive in his praise for Weisbrod.

Basically, the 45-year-old Harvard graduate—who may have cracked the NHL as a player if not for an injured shoulder—is just one of those people whose obvious smarts tend to make an impression. A longtime member of the Dallas Stars front office, Les Jackson’s history with Weisbrod dates back to the early 1990s, and he’s definitely a fan.

“Even if he didn’t go to Harvard, he’d be a smart guy,” Jackson said of the man who holds an English degree from one of North American’s most respected institutions. “He just has it.

“He can add something to whatever the conversation is.”

Jackson joined the Minnesota North Stars front office not long after the team had drafted Weisbrod 73rd overall in 1987, right before he began his four-year run at Harvard. Weisbrod was eventually part of the dispersal draft that saw a slew of North Stars form the core of the expansion San Jose Sharks in 1991, but a shoulder injury derailed the winger’s big-league dream.

At that point, the Syosset, N.Y. native decided to indulge the interest he’d always had in the management side of the sport and began working for the New Jersey Devils under GM Lou Lamoriello. He quickly became GM of the Devils’ top American Hockey League affiliate, the Albany River Rats, winning the Calder Cup in 1995, his second season on the job. In 2001, he guided the Orlando Solar Bears of the now-defunct International Hockey League to a championship and it was shortly after that his career took an interesting turn.

Both the Solar Bears and Magic were owned by Richard DeVos, and when the IHL ceased operations, Weisbrod took an administrative job with the basketball team. He was soon promoted to GM and chief operating officer of the Magic, where there was no shortage of big decisions awaiting him. Weisbrod did not believe McGrady—the face of the franchise—was truly the type of guy a team could build around, and traded him in a seven-player megadeal with the Rockets. Though the return was poor, many have since noted that Weisbrod was accurate in his assessment that McGrady wasn’t a lead horse. His instincts were also on at the ’04 NBA draft, where he opted for Howard instead of the consensus first pick, Emeka Okafor.

“That just shows the scope of his intelligence,” Jackson said. “He went in there and had to make some heavy decisions on some heavy contracts and players and situations.”

Despite asserting himself as a capable NBA executive, Weisbrod’s heart was in hockey and he jumped back into the game as a part-time pro scout with Jackson and the Stars in 2005. After one year in Texas, Weisbrod moved onto the Boston Bruins hockey operations department. There, he plied his craft beside Peter Chiarelli, the team’s GM and a former teammate at Harvard. Weisbrod’s stellar work as a college and pro scout was instrumental in helping the B’s claim the 2011 Cup. A few weeks later, he was hired as Feaster’s assistant in Calgary.

While Weisbrod and Feaster failed to find the magic tonic in Southern Alberta, Jackson is sure his former coworker will land on his feet, perhaps sooner rather than later.

“He’s not only a good player evaluator, he understands the concept of building a team,” Jackson said. “With his history in basketball, he’s good on the business side. He’d be a great guy for any organization to hire, he’s got a lot of tools to help a team.”