It seems like Eli Manning is always following in big brother Peyton’s footsteps.  He chose to play quarterback, he chose to play in the SEC (following Peyton’s offensive coordinator at Tennessee to Ole Miss), and he was drafted into the NFL with the first overall pick in his class.

In 2008, just one year after Peyton led his Colts to a Super Bowl victory, nabbing the MVP trophy for his efforts, Eli led the Giants to Super Bowl glory–and nabbed an MVP trophy for his trophy case as well, making them the first (and so far only) brothers to play quarterback in the Super Bowl and win Super Bowl MVP awards.

Along the way, like brother Peyton, Eli has managed to whore himself for numerous products, even working with Peyton on spots for Oreo and ESPN–although at $5 million in endorsements, he still has a way to go to catch Peyton’s $13 million.

And now, as the 2009 season approaches, Eli looks to be following in Peyton’s footsteps again, as his rookie contract is set to close out–by requesting a potentially team crippling contract from the team that has turned him into a star.

In March of 2004, Peyton signed a then record seven-year, $99.2 million contract, which included a $34.5 million signing bonus.  The deal was supposedly done to be somewhat cap friendly, accounting for roughly 10% of the salary cap each season–but in the end, Manning had to restructure the deal in 2007 to free up cap space for the team–and coming into 2009, he was still carrying a cap number of $21.2 million.

Along the way, despite winning the one Super Bowl, the Colts struggled at times to put together a solid defense, were unable to keep their Super Bowl winning offensive line intact, and were forced (before the Super Bowl win) to let star RB Edgerrin James leave via free agency.

Now, brother Eli is looking to cash in, with his rookie contract expiring–supposedly asking for a salary in the $20 million/year range, and his agents pushing for him to be the highest-paid player in the game.

While many executives estimate Manning will end up in the $15 million/year range, the total contract could be worth as much as $120 million, with more than $40 million guaranteed.

While less of a risk than giving unproven rookie Matthew Stafford a guarantee of $42 million, one has to wonder if in the long run, signing Eli to that big of a deal will mean the Giants might be merely a decent team, rather than potentially a great one.

So far, the only quarterback that I can think of that has essentially turned down more money to make sure that his team could remain competitive–and with his three Super Bowl wins, two Super Bowl MVPs, an NFL MVP, $9 million in endorsements, and Gisele Bundchen waiting for him at home, I don’t think anyone would say that Tom Brady made the wrong call.