When a 22 year old Phil Kessel came to Toronto, he was traded for uncertain picks - we knew the round, not the number. The Leafs, who finished dead last in the league in goals against the year prior, never addressed their goaltending needs. Phil Kessel bore the flak for years, as if he negotiated the trade, as if he posed a season's worth of .896 goaltending. He bought Burke more time than he deserved by masking the accountability of organizational weaknesses, and he did it without saying a word.
People wised up to organizational - rather than individual - failure and Burke was out. In came Dave Nonis, who promptly signed some of the worst contracts possible, often in the name of "character." He actively damaged the Leafs. Many of Toronto's "analysts" spent so much time critiquing pictures of Phil Kessel's chin, they couldn't even find Nonis' critics. Still no comment from Kessel or his agent.
People wised up to organizational - rather than individual - failure (again) and Nonis was out. Since then, Leiweke, Babcock, and Shanahan have all made not-so-subtle comments about the team "lacking character" to the press. Kessel must have known this was a reference to him, but never made any thing about it in public (and neither, as would've been more likely, did his agent). They didn't realize that veiled finger pointing to the press speaks more about "character" to me than first-on-/last-off-the-ice anyways.
Eventually, Phil Kessel had enough - not at the criticism levied at himself, but at his captain. Kessel came to the defense of his teammate, Dion Phaneuf, by highlighting that Phaneuf's individual failures weren't to blame for organizational failures (still), despite his dislike for talking to the media. It was framed as a "rant" without merit, of course, because the media cannot be wrong and the narrative is that Phil Kessel "doesn't stand up for his teammates."
Phil Kessel won the 2006-07 Bill Masterton award after not only recovering from testicular cancer, but coming back to play at the highest levels of hockey. Incredibly, this never gets mentioned when people are talking about what he eats for lunch. It never gets mentioned when people repeat that Phil Kessel is "soft."
He played 446 consecutive games for the Toronto Maple Leafs - the second longest such streak in franchise history, behind only Tim Horton. For this he was called "out of shape." He played the 47th most games of any Leaf, scored the 18th most goals, and 20th most points. For this, it's been said that he "wasn't the answer." Leafs' prospects looked up to him, and yet it was said he was "not a leader."
That's what's most remarkable about all this: the complaints about Phil Kessel's character are built entirely on unsubstantiated "analysis." The chattering class of doughnut-fetishists would rather ignore Kessel's words and actions to serve up lazy hit pieces. There's no story about taking a helicopter to New York, nothing about sleeping with teammates' wives, nothing about drugs or parties or any of the usual things that get attached to "low-character" guys.
His GM spoke highly of his character. His teammates spoke highly of his character. A rival player spoke up for his character. But the opinions of people in the know don't matter because the assassination of Phil Kessel's character was built on nothing but "he doesn't look like how I think an athlete should look" and "he doesn't talk as much as I think an athlete should talk." For this drivel, people like Simmons and Feschuk are paid money.
What the Leafs have to show for moving a high-character, high-skill player (at a discount!) is 30 spots in the draft, a second-line-maybe-first-line forward prospect and a third-pairing-maybe-second-pairing defensive prospect. This is the most benefit they thought they could get for Phil Kessel not just this offseason, but for every deadline and offseason over the next seven years as well. And yet somehow media personalities masquerading as hockey analysts dare to say the removal of Kessel's "character" means this trade makes the team better.
It's probably for the best: Phil Kessel deserves to be on a team that has a chance to win, rather than a team that's woefully uncompetitive at every position. He deserves a media that's capable enough to convey Kessel's character with facts instead of lazy pot-shots. He deserves a Stanley Cup. And why shouldn't he? After all, he's a nice guy. He tries hard. He loves the game.