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Insider Only Latest Pirates Buzz: Should the Pirates be willing to trade Jameson Taillon as part of package for Justin Upton?

Pirates expressing interest in Upton, Quentin & Headley

Major-league sources tell the Pirates have had preliminary trade discussions regarding two power-hitting outfielders, San Diego’s Carlos Quentin and Arizona’s Justin Upton. Talent evaluators from those two clubs have scouted Pittsburgh’s minor-league affiliates in recent days, as the teams prepare preference lists of prospects they want in the potential deals.
According to the report, “It seems unlikely the Pirates would acquire both Quentin and Upton, but they have a strong desire to upgrade their lineup by landing one of them.”
As the report indicates Quentin would come at a lower prospect price, because he’s eligible for free agency after this season. Upton though is extremely intriguing but would command a larger package, since he’s under contract through 2015.
Upton, 24, is hitting .267 with 7 home runs and 36 RBIs and while he’s having a down year, Upton finished fourth in MVP voting last season and had 31 home runs and 88 RBIs in 2011, including 39 doubles and 21 stolen bases. The intrigue of the Pirates teaming up a star player next to Andrew McCutchen for the next several years is a big factor in the Pirates pursuit of Upton.
“Upton would be the bigger splash for an organization seeking to reestablish itself. Upton’s relationship with the Arizona franchise has soured recently amid criticism from owner Ken Kendrick, but he’s highly regarded within the industry. A change of scenery may be the best thing for Upton. If he lands in Pittsburgh, he would combine with McCutchen to give the Pirates their best collection of star talent since the departure of Barry Bonds, ” Jon Morosi of Fox writes.
If the Pirates want to go all in for Upton, it might come down to their willingness to move top pitching prospect Jameson Taillon as the Pirates won’t move Gerrit Cole under any circumstances. Taillon has been viewed as an untouchable but if you’re getting a star outfielder at just 24 years old, who’s already established at the Major League Level, management has to consider the possibility as Taillon is no sure thing. A package centering around Taillon in exchange for Upton would upgrade the Pirates significantly at the Major League Level for now and the future.
Look for Starling Marte’s name to also pop up if talks progress between the Pirates and Diamondbacks.
Meanwhile, Quentin, 29, is hitting .273 with 7 home runs and 17 RBIs in 32 games this season. Quentin started the season injured and didn’t make his season debut until May 28th. Quentin is making $7.025 million this season. The Pirates also have interest in Padres third baseman Chase Headley and it’s possible the team could try to land a package deal of Quentin/Headley from San Diego if the Pirates lose out on Upton. That scenario would also uprade the team significantly at the MLB level and Headley is under contract after this season.
Signed a six-year, $51.25 million contract on March 3, 2010: Made $4.25 million in 2011, followed by salaries of $6.75 million in 2012, $9.75 million in 2013, $14.25 million in 2014, and $14.5 million in 2015. Upton has Limited no-trade protection and may block deals to four clubs: Cleveland, Detroit, Kansas City and Oakland.

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William DePaoli

TIOPS Insider

William DePaoli is the President/Founder of Inside Pittsburgh Sports LLC and can be reached at

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