Brady, Bird, Orr? Who Is The Greatest Leader In Boston Sports History?

Fortune magazine raised some eyebrows Thursday with a subjective, arbitrary and annual list of the world’s greatest leaders.

The list included the usual suspects — the Pope, Jeff Bezos, Angela Merkel — but the real surprise was who occupied the top spot: Chicago Cubs president of baseball operations Theo Epstein.

Even Epstein was surprised by the “honor,” instead giving credit to the rest of the organization. But given Epstein’s ranking on the list and his ties to Boston, and given the relative sports inactivity associated with late March, we figured we’d try to pinpoint the best leader in Boston sports history.

And the nominees are …

Bill Belichick, Patriots head coach
The résumé alone speaks for itself. Belichick has five Super Bowl rings since taking over in Foxboro, and he’s poised to add at least one more before riding off into the Nantucket sunset. That success didn’t come solely from being the smartest football guy in the room, though. Belichick has an innate ability to get the most out of his team by stressing the greater good of the club while not (outwardly, at least) placing too much credit or blame on one player. He’s got arguably the best quarterback of all time at his disposal, but he’s not afraid to berate him in front of the football team. Which brings us to our next choice …

Tom Brady, Patriots quarterback
We all know Brady fell to the sixth round of the 2000 NFL Draft in large part because of questions about his on-field ability. Even then, however, folks marveled at his leadership. Brady obviously turned himself into an all-time great, and he’s also turned himself into an all-time leader. He clearly speaks with authority and is able to inspire teammates that way, but no one prepares better than he does allowing him also to lead by example. You also don’t erase a 25-point lead late in the third quarter of the Super Bowl without an ability to lead.

Red Auerbach, Celtics coach/executive
We’ll keep this short and sweet: Auerbach was part of 16 NBA titles in 29 years. That’s absurd. He’s also considered the cornerstone of arguably the most successful franchise in American sports history. They build statues of you for those kinds of accomplishments.

Bill Russell, Celtics center/coach
Alongside Auerbach, Russell reached unparalleled levels of success with the Celtics. He won 11 NBA titles, and he won two of those rings as a player-coach, no less. He did all of that as a black man in the 1950s and ’60s in Boston, a city with a complicated history when it comes to race relations.

Larry Bird, Celtics forward
“Leadership is diving for a loose ball, getting the crowd involved, getting other players involved,” Bird once said. “It’s being able to take it as well as dish it out. That’s the only way you’re going to get respect from the players.”

Check, check, and check.

Oh, and also the three NBA championships in a golden era of the NBA. Can’t forget about those, either.

Kevin Garnett, Celtics forward
Garnett’s time in Boston was relatively brief, but when Boston acquired him from Minnesota, he instantly changed the culture. He held every teammate, coach, fan — you name it — accountable. He was the vocal leader, and he led with his play. And despite being the most talented player on a team filled with talented players, no one worked harder than Garnett.

David Ortiz, Red Sox designated hitter
When the Red Sox acquired Ortiz in 2003, the move came with little fanfare. Hardly anyone even noticed. But when he retired in 2016, Ortiz got a league-wide goodbye tour. In between, Ortiz redefined the Red Sox, driving an evolution from perennial losers to perennial World Series contenders. His clutch play was the on-field backbone of those teams, surpassed perhaps only by what he did in the clubhouse where teammates swore by his leadership.

Terry Francona, Red Sox manager
That there have been 45 managers in Red Sox history tells you all you need to know about the difficulties of the job. Only one manager won more games than Francona, and he’ll forever be remembered as the manager who helped lead Boston to its first world title in 86 years, adding another three years later. He led the Red Sox for nearly a decade and did so when there was more popularity, attention and controversy than perhaps any other time in team history. And he did so while managing some larger-than-life (and often times difficult) characters.

Jason Varitek, Red Sox catcher
The Red Sox valued Varitek’s leadership so much, they named him captain after the 2004 season, the team’s first captain in nearly 15 years. He quietly went about his business but wasn’t afraid to speak up when it was needed.

Bobby Orr, Bruins defenseman
Orr makes any list of “Boston’s best ____” and this is no different. He’s the best player in franchise history, and his list of accomplishments would be even longer had his knees cooperated. But this quote from Ken Dryden, a longtime rival, says it all about Orr.

“He brought others with him; he wanted them involved, That’s what made him so different: It felt like a five-player stampede moving toward you — and at his pace. He pushed his teammates, [because] you’re playing with the best player in the league and he’s giving you the puck and you just can’t mess it up. You had to be better than you’d ever been.”

Thumbnail photo via Bob Donnan/USA TODAY Sports Images

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