Everyone knows the details of his first contract which he signed with the Atlanta Falcons before eventually landing in prison and bankruptcy.
This time around, the Eagles feel that they have made a smarter investment in a player that they will look to carry their offense over the coming years.
However, was it really prudent to give a 31-year-old quarterback with questionable durability such a lucrative deal?
Vick's new deal undoubtedly helps the team in the short term, as he has freed up two million dollars from this season's cap that could go towards bringing in a veteran linebacker such as Lofa Tatupu.
The Eagles are a smart organization, however, and will not sacrifice long-term efficiency for one good season. With Andy Reid at the helm, you will always expect the team to make prudent moves, and many people will see locking up the face of the franchise as a prudent move.
No matter how you look at this particular move however, there are a lot of risks and seemingly more questions than answers.
In Vick, the team gets a player that has had one season of being an elite quarterback and another of being an elite playmaker.
Vick will never be able to repeat his feat of 2006, when he ran for over 1,000 yards as well as throwing for 20 touchdowns. Even if he does still find a way to put up those rushing numbers, he would need to drastically improve on his 75.6 quarterback rating from that season.
That leaves the Eagles with last season as the only real way to judge Vick. He was stellar. There is no doubting that he was the second best quarterback in the league in the regular season.
It was the first season in which Vick had a quarterback rating of over 100 and still put up over 600 yards rushing. However, once again, 2006 remains the only season when Vick completed a full 16-game schedule.
Even if you include the first game of the year when Clay Matthews took Kevin Kolb out, Vick still only played 12 games last year and missed the rest through injury. That would be fine except for the fact that Vick has had these issues even during his younger years. As Peyton Manning is finding out, injury issues don't get any less serious when you get older.
This is why it seems foolish to invest so much money in Vick at this stage in his career.
Eagles fans won't like to hear it, but the truth is there is still a chance that Vick is a one-season wonder. He never showed the type of accuracy and good decision-making he showed last year. While fans are hoping that that is a result of his maturity and the influence of Reid, it may not be.
Vick is not a proven passer over the years in the sense of a Tom Brady or Peyton Manning. He won't be able to simply sit still in the pocket and dissect the opposing defense on every play for the next six years.
He has to rely on his athletic ability, and as such, he will get hit, in turn leading to more injuries.
The Colts took a huge risk in rewarding Peyton Manning with his huge deal at his age, and that was before his neck injury. Even though Manning had never missed a start and was crucial to the team and franchise, he is coming to the end of his career. While it is always difficult to let the greats go, it is something that always must be done.
Vick is a huge player for the Eagles for the coming season; it is safe to say that the Eagles season hinges on how far he can take them, but does anyone really think we will still be saying that in six years time?
Or even five? Four? Three?
A 34 years old, Vick doesn't figure to be anywhere near as effective as a 34-year-old Manning or Brady, but he will now be earning just as much as them.
For all those people that defend Vince Young and believe that he is such a talented quarterback, why aren't the Eagles investing in him when he would be the much better long-term option?
Would it not have made more sense to invest in Young at a cheaper rate without waving Vick's illustrious deal in front of DeSean Jackson and essentially taunting him? The truth is it is going to be nearly impossible to re-sign Jackson now.
Jackson wanted a new deal before this season and after seeing the team grossly overpay Vick, he will demand similar treatment. How does the team do that having already gotten some huge contracts on its books?
Is Jackson the kind of guy to offer out a hometown discount? I'll leave you to make your own assumptions there, but I doubt it.
Personally, I believe the Eagles had to re-sign Vick, as Young isn't going to carry any team to the Super Bowl, but six years and $40 million guaranteed is way above his market value.
The amount of money per season is perfectly fine, but the length of the contract can't be any longer than three to four years, unless they have sculpted it so he can be cut or released without causing too much cap concern later on.
If the Eagles expect to get 13 regular season games out of Vick behind that mismatch of offensive linemen this season, they will be lucky.
If they expect him to still be a star at 35, 36 or 37 years of age, they'll be dreaming.