There's a higher likelihood that Crawford gets traded or hits the free agent market after 2010. As Nick Cafardo noted, that $10 million is too rich for the small market Rays. Crawford is a great player who will command more than $10 after this option is up. That doesn't preclude the Rays and Crawford from talking about a contract extension. Crawford seems willing to listen to what the Rays have to say. The Rays would like to keep one of their franchise players.
The deal is unlikely to happen. Signing another long-term deal would preclude Crawford from ever testing the free agent market. He's already signed away two of his free agency years. Signing another long-term deal would eat up more of Crawford's free agent time. As John Romano notes, Crawford also doesn't like the turf at Tropicana Field. A park with natural grass would help Crawford and lengthen his ability to run. Of course, there's also a business side. By the end of Crawford's deal, he'll have earned about $31 million, a sum that can best be described as a bargain for a player with Crawford's talent and abilities. If Crawford wants a Johnny Damon-like contract (4 years/$52 million), the Rays will be in trouble. As a low-revenue team, the Rays can't afford it.

The Rays have been asked about B.J. Upton, but not about Crawford. Yet. Don't expect them to part with both of them. A team that should again be part of the AL East race can't afford to get rid of two-thirds of its outfield, leaving a platoon in right field. Upton and Crawford are too important to the Rays to be traded away at the same time.

The Rays would need to be blown away by a big offer for either outfielder. Both are talented. Even with Upton's down year in 2009, each would command a nice haul of young talent. What happens with Crawford, and possibly Upton, depends on how the Rays are doing in the standings at the trade deadline. If the Rays are down, Crawford will be shopped. If they're in contention, they'll keep Crawford and let him walk when he should be a Type A free agent as opposed to a Type B. To give up on Crawford now, the Rays would need to be completely blown away by a Hot Stove trade offer for him. While Crawford could become an attractive alternative for big market clubs chasing Matt Holliday and Jason Bay, it might be more prudent for the Rays to wait. At present, Crawford's worth is diluted by the fact that outfield is the deepest position in free agency. Not many free agent outfielders have the tools Crawford possesses. But a market saturated with outfielders does not bode well for a good return for the Rays. While waiting, the Rays get a chance to negotiate and see if a deal can be brokered. With big name free agents out there, it's too early to think about dealing Crawford away.

Chances are good Crawford's final days as a Ray are approaching as he gears up for a payday from one of the bigger market franchises. We'll see how it plays out this winter.

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