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Thinking Through A B.J. Upton Extension

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I know, I know - just yesterday I was saying the Rays are still likely to trade B.J. Upton over this offseason, so what's this talk about an extension? But there was a great conversation in yesterday's comments and while I don't want to simply rehash the entire discussion, I think this topic deserves some fleshing out.

The Rays essentially have three options with Upton: trade him over the offseason, keep him and trade him at next year's deadline, or sign him to an extension. So what are the pros and cons of each option?

Trade Him This Offseason: The Rays likely get the best return possible for Upton, as there aren't going to be many attractive free agents center fielders on the market and he'll have a full season of team control left. This return likely won't be much different than what we were forecasting for Upton at this year's deadline, though --  -- and could just as well be smaller. It depends on how desperate other teams get for an outfielder.

Keep Him and Trade Him at the Deadline: If the Rays want to make a push for contention in 2012, they would have a better team if they kept Upton and started the year with him. They could still deal Upton at the deadline if they fall out of the race, but then they'll be getting a smaller return for Upton. And if the Rays stay in contention all season and don't trade Upton as a result, there's a decent chance that the Rays could get no compensation for him when he becomes a free agent.

Sign Upton to an Extension: The most convincing argument I've seen in favor of this option is Kevin's post from this morning on the weaknesses in the Rays' minor leagues. Up to this point, the Rays have been able to trade away players as soon as they become expensive and not miss a beat. Their minor league system was churning out prospect after prospect, so there have been a multitude of players ready to fill in whenever someone was traded.

But after Brandon Guyer gets promoted, the Rays will have no more exciting position prospects left in the high minors. It's going to be a number of years before Josh Sale and company reach the majors, meaning any holes the Rays develop in the outfield they would need to fill some other way. Keeping Upton would allow the Rays to play Jennings in left field and Guyer in right field, keeping Ben Zobrist at second base and putting Matt Joyce at 1B/DH and switching out with Guyer.

Without Upton, the Rays would need to rely on Guyer and Joyce as an everyday guys (which I think they can be), and they'd still have a hole at 1B/DH. So keeping Upton would make the Rays a stronger and deeper team, but how much would he cost? He's likely to get around $7 million this year in arbitration (guess/estimate, but it seems reasonable), so someone yesterday suggest something like a three year deal at $7/9/10.5. 

Would Upton go for something like that? It's tough to say; it really would depend on how much he wanted to stick around in Tampa Bay versus hitting the free agency market. He'd make more money by hitting the market, but he'd get to stick around in TB for a few more seasons this way while having some security. 

The Rays are going to start having some hard choices to make. Over the last few seasons, many of the moves were pretty obvious -- the Garza and Bartlett trades were both forshadowed and anticipated considerably, for example. But the Rays have a wide range of ways they can move going forward. Do they trade Shields, or do they shop Niemann/Davis instead? Do they invest in Upton, even if that means they can't invest in other players for as long? Do they make a big push to win in 2012, and if so, do they push Matt Moore toward the majors faster?

But anyway, I'm getting way ahead of myself -- it's still the regular season and we've still got lots of baseball to enjoy before having to ponder this sort of stuff more in depth.