Ron Jaworski won an NFC title, but was constantly criticized for his immobility. Randall Cunningham's physical gifts and eye-popping statistics couldn't hide his erratic play or enigmatic manner. Donovan McNabb set a slew of records but, his critics droned, too many passes landed at receivers' feet.
Now beginning what essentially is his fourth year as the Eagles starter, with the added challenges of both a new coach and a promising though raw backup in Nick Foles, Vick must try to appease a public that has tolerated but never treasured him.
Like any Eagles quarterback, Vick, who arrived here burdened with personal baggage and a reputation for inconsistency, will be constantly tested, intensely scrutinized.
"I came back to help this team win football games," he said when questioned about this season's impact on his career. "I can't worry about my future. I can only worry about now. The past is history, the future is a mystery."
Success for him will be judged on many levels.
He must prove he is durable in a Chip Kelly offense that will put him at risk more often.
He must show that he can be the passer who three years ago torched the Redskins for 333 yards and four touchdowns, not the scatter-armed quarterback who has turned up in too many games since.
And, thrust into the complexities of Kelly's go-go attack, he must convince his skeptics that he can fully grasp it.
"We don't consult with Mike on what we do," Kelly said when asked if Vick contributed to the game plan. "But we always talk to all our quarterbacks. 'What are [the opponents] like? What are they like on third down? What would you call in those situations?' A big part of what we do is what our quarterbacks feel comfortable running."
Should he comfortably run Kelly's read-option and lead the Eagles to a plus-.500 record, Vick will forestall the "We Want Nick!" chants and perhaps earn an extra year or two on a contract that will pay him at least $7 million this year.
Failure, of course, will be easier to gauge.
Should Vick, say, throw an ill-timed interception in an opening-game loss to the Redskins or misread coverage at a critical time, the howls will roar through Philadelphia like a hurricane.
Already, before he has thrown an official 2013 pass, there is carping about Vick on talk radio. In his ranking of 32 NFL quarterbacks for ESPN.com, Jaworski rated him 25th.
Even Kelly, given a chance to praise the man who will operate his offense, curiously sidestepped the opportunity.
Two hours before Vick met the media Wednesday, the new Eagles coach was asked whether the 33-year-old could be considered a "franchise quarterback," a label Vick later said he desired.
"He's the Philadelphia Eagles quarterback," Kelly cryptically replied. "And if that's a franchise, then the answer is yes."
Some teammates insist that Vick has looked more confident and relaxed this preseason.
"I see a more determined Mike," said wideout Jason Avant. "He's got a look in his eyes that says he's focused and ready to have a great season."
That comfort level could be due to Kelly's system, which seems better suited to Vick's many physical skills. But it could also be the result of what happened recently in a Virginia courthouse, where an enormous financial and mental burden was removed.
It was revealed that Vick has settled the bankruptcy issues that followed him from prison four years ago. The court has approved his plan to repay $20 million to creditors.
It's rare, his lawyers noted, for a Chapter 11 case to be settled so quickly and thoroughly.
"It was a problem life dealt me," Vick told the Norfolk Virginian-Pilot. "You can't take something from somebody and not replace it. I had obligations and responsibilities that I had to take care of."
Mental outlook aside, how well Vick does this season will depend on how healthy he remains in a sleight-of-hand system that invites quarterback contact.
"It's football. You're going to get hit," Vick said when asked about the possibility the fakes and ballhandling Kelly demands will take a toll. "If you go into a game knowing you're going to get hit, then it's easy to deal with."
Kelly said he and his staff have tried to gird Vick for the likely assault.
"We've talked to Mike about that," Kelly said. "We haven't seen anything in the preseason that would make us nervous about teams teeing off on a guy that doesn't have the ball in his hand.
"Mike understands people are going to run at him when he's carrying out fakes. But I think that's the same for any quarterback. . . . [Besides], somebody has to catch you first, right?"
If this turns out to be Vick's last stand, the timing is odd. All around the NFL, athletic young quarterbacks - like the Redskins' Robert Griffin III - are following the Vick template of strong arms and quick feet.
Ironically, last season, as he and the Eagles scuffled to a 4-12 mark, Griffin, Russell Wilson, and Colin Kaepernick were constantly compared to Vick.
"It means a lot to me," Vick said. "It means the way I've played the game has trickled down to the younger generation. It's great that you have guys who respect what you do. You want everybody to like you. You want to be that franchise guy."
Even if your coach and a city's fans need convincing that you are.
Contact Frank Fitzpatrick at email@example.com. Follow on Twitter @philafitz.