Why is it difficult?
He's got all the raw tools you could ever ask for in a NFL signal-caller and is loaded with elite upside. But, he's only a one-year stater, has a longer, inconsistent delivery and still has to improve his coverage-reading abilities.
That's the definition of a prospect who could go anywhere from the second to the fifth round.
After examining a variety of possibilities, I've narrowed it down to one team for the wildly intriguing quarterback prospect: the San Diego Chargers.
The fit is perfect.
Philip Rivers has been on the verge of that "elite" quarterback status for a while now, and is certainly the team's signal-caller in the foreseeable future.
Osweiler isn't ready to start this year and probably won't be in 2013, either. He'd be a Ryan Mallet-esque selection by a club with an established veteran quarterback in place. His huge arm and downfield accuracy would be ideal for the Chargers' downfield passing attack.
Under the tutelage of the 30-year-old Philip Rivers, one of the better downfield passers in the league, Osweiler can learn the nuances of the game and mold his game accordingly.
Remember, Rivers entered the league as a fiery kid with an odd, sometimes unreliable delivery, too. Osweiler will join the NFL with a stronger arm and more athleticism than Rivers had when he was picked in 2004.
No, Osweiler wouldn't be the backup in 2011. Billy Volek is one of the more reliable backups in the NFL, but he was cut and the team signed Charlie Whitehurst from the Seattle Seahawks.
Even if he's the primary second-stringer for the next two seasons, that's fine.
The former Gonzaga basketball recruit can easily acclimate himself to the warm climate of San Diego, after playing his college ball in Tempe, Arizona.
The Chargers don't have a ton of holes to address in the 2012 draft, and taking a mid-round flier on Osweiler has the potential to be one of the smarter draft decisions general manager A.J. Smith has made in a while.
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