Trading Justin Upton: There's Not A Deal For Every Player

As part of SB Nation United, you're going to be seeing some new voices at AZ Snake Pit, SBN featured site contributors writing about issues both local and national. Think of them as guests in the community. We're beginning this week with Michael Bates, better known as one of the minds behind The Platoon Advantage.

I keep hearing about how little Kevin Towers and Ken Kendrick think of Justin Upton, and how Upton's bound to be playing elsewhere come next April. That may happen, but I'm having a harder and harder time seeing how the Diamondbacks come out of any deal looking like a winner. We like to think that if a general manager is savvy enough, any player is tradable for a good return, but sometimes holding on is not only the best option, it's the only option.

Upton is a former first-overall pick who hit 31 homers last year at age 23, with an OPS+ of 140, but who has slumped to .277/.354/.426 and just 15 homers in 2012. Despite his struggles, the price to acquire a player with Upton's ability should be ridiculously, and probably prohibitively, high. Aside from their general rarity, there's a reason that we don't see 24-year-old, vaguely disappointing, almost-superstars change teams very often: it's incredibly hard to get an acceptable value for them.

This is especially true when they come with too many question marks, as Upton does, for other teams to break their banks for them (especially if the player's owner and general manager have publicly slagged him). Given that disincentive for the buyers, it creates one for the sellers, who can have no interest in letting a putative star go cheaply only to watch him put up a 6- or 7-win season somewhere else.

Reports this summer had Arizona seeking major-league talent in return for Upton, and while that kind of trade is certainly more achievable in the offseason than during the pennant race, in recent years we've seen relatively few straight-up baseball trades that involved major-league veterans on both sides that weren't motivated by money. It's tempting, of course, for frustrated Diamondbacks fans to put their faith in Towers, who has been a successful GM in the past, and assume that any deal he makes to unload Upton will bring back enough value to offset the loss.

Indeed, as my colleague Mark Smith pointed out last year, we generally don't give team executives enough credit for being as smart as they are. That said, we also don't take into account how human they are as well. General managers are subject to emotional weakness just like the rest of us, and are fully capable of acting out of fear, frustration, or desperation-or simply because they feel obligated.

I followed the Twins as former GM Bill Smith tried to trade Johan Santana in the winter after the 2007 season. Smith tried desperately to get major-league-ready position prospects out of the Red Sox and Yankees to fill holes in the starting rotation and center field. At one point, Boston had reportedly offered Jed Lowrie, Jacoby Ellsbury, and Justin Masterson or Jon Lester, Coco Crisp, Lowrie, and Masterson for the Twins' ace. The Yankees had offered Phil Hughes, Melky Cabrera, and Ian Kennedy. The Twins overreached, drove both clubs away, and ended up with just one bidder left, the New York Mets.

The Mets didn't match up well with the Twins. They had extremely raw center-field prospect Carlos Gomez, and three pitching prospects. one of whom was just 19 and the other two were projected as mid-rotation starters at best. The Twins should have walked away. With Santana in their rotation, they would have easily beat out the Chicago White Sox for the AL Central title and recouped two draft choices after Santana left as a free agent that offseason.

Instead, having made the only deal left to them, they finished tied with Chicago, lost a one-game playoff, and wound up with a center fielder who couldn't get on base (Gomez had a .293 OBP in 963 plate appearances as a Twin), two total disappointments in Phil Humber and Kevin Mulvey, and one young pitcher who stalled in the system and is still trying (and failing) to make it as a reliever. Smith and the Twins had become too invested in the idea that they had to trade Santana before 2008 started, and had too much institutional momentum to stop themselves.

The truth is that there isn't an acceptable deal out there for every player, and no matter how frustrating that player can be, entering any offseason believing that a deal is necessary and inevitable is dangerous. The Diamondbacks will have just as much of a shot at the 2013 NL West as those 2008 Twins did in their own division, and to throw away a chance at that division title over frustration, or spite, or a mistaken belief that it's easy to replace a potential superstar is just as foolish.