Justin Upton TBOH Staff Pick: New York Yankees


The New York Yankees should be major players for the big contract free agency battle for big talent Justin Upton.

Any contender would be happy to add the 28-year old power-hitting outfielder who will play most of the 2016 season at that age.

However, there are two major obstacles. First, he could prove to be one of the most expensive free agents in baseball history, dollars-wise. Second, the cost to add him will include surrendering your top 2016 MLB Amateur Draft pick.

Another potential obstacle to his signing with some of the major contenders is his status as a corner outfielder, where a number of teams appear set. Of course one of the incumbents for such a team could possibly move in to first base, or if an AL club, the DH position could be split.

Upton was the first overall pick in the 2005 MLB Amateur Draft by the Arizona Diamondbacks out of Great Bridge High School in Chesapeake, Virginia. He is the brother and former teammate of Melvin Upton, who was the 2nd overall pick in the 2002 MLB Amateur Draft.

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Justin has proven the more productive brother over the long haul. He has a career .271/.352/.473 slash line with 190 home runs, 616 RBI, 694 runs scored, 234 doubles, and 115 steals across parts of nine big league seasons spent with Arizona, the Atlanta Braves, and the San Diego Padres. He is a three-time NL All-Star, including last season, and has won a pair of Silver Slugger Awards.

Upton has been the central figure in a pair of big trades in back-to-back calendar years. In January of 2013, the DBacks dealt him away to the Braves along with Chris Johnson for a five-player/prospect package that included Martin Prado, Nick Ahmed, and Randall Delgado. There he first teamed with his brother.

Then in December of 2014, Upton was traded away by Atlanta along with prospect pitcher Aaron Northcraft to the Padres for a four-prospect package that includes two, pitcher Max Fried and outfielder Mallex Smith, who are now considered among the Braves’ top 10 prospects.

There has been some speculation that Upton could go to a dark horse team, such as the Chicago White Sox, Seattle Mariners, or Cleveland Indians. The Baltimore Orioles could be a landing spot if the O’s are unable to bring back slugger Chris Davis. A pair of west coast clubs, the Los Angeles Angels and the ever-present San Francisco Giants could also move on him.

Among our staffers, only two had him going to the deep-pocketed Yankees: Ethan Witte and Ryan Gerstel. Ethan believes it will take something like a “7-years, $145 million” deal to land his services. Ryan stated that “it wouldn’t be a true MLB off-season if the Yankees weren’t involved,” and called Upton “the power from the right side of the plate that the Yankees desperately need.

Ethan could be close to right-on in his contract speculation, and has industry support for his call. Dave Cameron at Fangraphs stated  “I don’t think Upton presents a lot of risk of total failure, but at the price he’s likely to get, I don’t see him performing at a level that justifies the expenditure,” speculating that it will take that $20 million per season to gain his services.

Wallace Matthews at ESPN feels that he is indeed a Yankees option, but likes another free agent who we will spotlight here at TBOH later, Jason Heyward, a bit more: “If the Yankees are going to add a high-priced outfielder for 2016, they’re probably better off bidding hard on Heyward while reserving Upton as a more-than-acceptable second choice.

This is yet another free agent who could go almost anywhere. Besides our pair of TBOH staffers sending him to the Big Apple, we were wide-spread in our call at to his ultimate destination.

I went with the Indians, David Mosemann had him to the Orioles, Tyler DiSalle sent him to the Texas Rangers, and Alexis Girardo picked the Giants.