Trade partner No. 1: Kansas City Royals
To get Upton, the Royals would have to forfeit top prospect Wil Myers. Myers is the minor leagues' best right-handed hitting position player and projects as an impact middle-of-the-order bat. With no service time, this would save the D-backs approximately $30 million and give them more control years. Also, they have lots of young pitching in their system, so if they do deal Upton, it would make sense to get an impact bat.
Why would the Royals do this? Well, it's possible they don't want to wait for another prospect to develop and need another impact right-handed bat in their lineup. Also, Upton is signed through 2015 and will average roughly $13 million in salary the next three years, which is a figure the Royals can afford. Put Upton in that lineup and it could be the best in the AL the next three seasons.
Trade partner No. 2: Atlanta Braves
An equitable exchange for Upton would have to involve outfielder Jason Heyward. This would give the Braves better righty-lefty balance in their lineup, and again, the D-backs would save money and add control years. It also comes down to which outfielder will reach his ceiling first, as both have MVP potential. Heyward has started to heat up, so it's hard to see Atlanta dealing its homegrown, hometown kid, but it's fun to think about an old-school challenge trade like this, the kind you don't really see anymore.
Trade partner No. 3: Texas Rangers
Upton’s value could probably command a return of Jurickson Profar and Mike Olt, the Rangers’ top position player prospects. However, the only way I can see the Rangers even thinking of this deal is if they can't re-sign Josh Hamilton and need a middle-of-the-order bat to replace him. Profar is as untouchable as any Rangers farmhand there is and is the game’s best shortstop prospect, but he is currently blocked at the big league level by Elvis Andrus (just as Olt is blocked by Adrian Beltre). If the D-backs do somehow manage this deal, it could set up their left side of the infield for the next eight years. Only then would it make sense.
Trade partner No. 4: Detroit Tigers
Like the Rangers, Upton probably requires the Tigers' top two prospects in third baseman Nick Castellanos and right-hander Jacob Turner. Castellanos, who stood out at this year’s Futures Game, has a chance to be one of the AL's best third basemen someday, but he is blocked in Detroit right now. He can really hit and his power should come in time. Turner has a high ceiling as well, and to trot him out with young hurlers Trevor Bauer, Tyler Skaggs and Wade Miley would set up the D-backs’ rotation for years. For the Tigers, it would give them a third impact bat behind Miguel Cabrera and Prince Fielder and improve their defense in right field. And when Victor Martinez comes back in 2013, it would give the Tigers -- who are clearly in "win-now" mode -- arguably the best lineup in the AL.
Trade partner No. 5: Pittsburgh Pirates
Given the current parity within both leagues and the addition of another wild-card berth, there are more buyers than sellers, and even the Pirates are getting in on the act. The opportunity to acquire an MVP-caliber power hitter at such a young age is a value a team like the Pirates cannot afford to overlook. To do that, they’d have to give up former No. 1 pick Jameson Taillon and future leadoff man Starling Marte. The Pirates could afford giving up Taillon if they hold on to Gerrit Cole, the No. 1 overall pick in the 2011 draft. It would be worth it to sandwich Upton between Andrew McCutchen and Pedro Alvarez to form a very dangerous middle of the lineup. Marte would offer the D-backs the leadoff man they’ve lacked for so long, and like Turner would do, Taillon would bolster a talented, young rotation in Arizona.
Upton might be having a down year, but his trade value is based somewhere between his performance last year and his potential -- which is as a Hall of Famer. Therefore, the asking price should be sky-high. The fits are limited, leading me to believe that Upton still will be wearing a Diamondbacks uniform long after the July 31 trade deadline has come and gone. However, the mere fact that the D-backs seem to be listening on Upton suggests something could happen.
