For a brief moment in time, the entire belief made a lot of sense. 

It was too logical not to.

Major League Baseball’s free agency and trade market had seen the predictable run on starting pitchers, and even a bunch of relievers. Then, somewhat predictably, the biggest position player on either market, Jason Heyward, signed his megadeal with the Chicago Cubs for $184 million over eight seasons.

After that, if figured to be time for the best of the rest, especially the outfielders. Among them, Justin Upton and Yoenis Cespedes were the headliners, but surprisingly, they remain on the marquee going on two weeks after news of Heyward’s agreement came to light.

While those two are still on the board, it is certainly worth examining why and how much each is worth, obviously using Heyward’s massive contract as a barometer. Neither Upton nor Cespedes should reach those heights in years or total money, but both deals stand to be significant—sooner or later.

“I don’t remember it ever being separated like that,” Cubs president of baseball operations Theo Epstein told ESPN’s Jerry Crasnick days before his team agreed to terms with Heyward. “There was just more supply and more demand for pitchers than anywhere else, and outfielders came next. Everyone is just waiting for the first one to sign.”

The first one has now, yet there is still little to no movement on the markets for Upton or Cespedes, as well as Alex Gordon, who is seen as another premier outfield option, though one who will receive a lighter contract than the other two because he will be 32 years old next season.

All three can make cases to top $100 million in the open market, but Upton and Cespedes are locks to do so.

Upton, a former No. 1 overall pick by the Arizona Diamondbacks, is going into his age-28 season and is coming off three very good seasons, all of which were played in the traditional pitcher-friendly parks of Turner Field and Petco Park. In those three seasons with the Atlanta Braves and San Diego Padres, Upton has averaged 27 home runs a year and put up a 126 OPS+.

He has been durable and consistent, a knock on him during his five seasons with the Diamondbacks, as his OPS+ totals fluctuated from as low as 107 to 141 in that time. That unpredictability, which led him to be tabbed by his first organization as an underachiever with five-tool talent, led to Upton being traded to the Braves, who flipped him to the Padres after two productive seasons in Atlanta.

Having absolutely proven he can be a middle-of-the-order bat, Upton’s market figured to be flush with suitors this offseason. But through November, the winter meetings and now headed into Christmas and the end of the year, there has been only quiet rumors regarding Upton. The Baltimore Orioles seem to be a realistic option and fit—the Orioles need an impact bat, could use an outfielder, and Upton is from bordering Virginia—but there’s been little traction there since CBS Sports’ Jon Heyman reported the team met with Upton’s agent before Heyward signed with the Cubs.

The San Francisco Giants and Los Angeles Angels have a need for a power-hitting outfielder, but the Giants took themselves out of that market after signing Johnny Cueto last week, and Angels owner Arte Moreno told reporters (per Bill Shaikin of the Los Angeles Times) his team will not pursue Upton or Cespedes. We should not completely count out either club, though.

If they truly are out on either player, it would hurt both players’ leverage. However, Upton being the youngest of the remaining options and still a premier outfielder in his prime means a huge contract is in play. Tim Dierkes of MLB Trade Rumors predicted a seven-year, $147 million contract, and that kind of deal, and maybe even a richer one, still seems plausible considering what outfielders like Matt Kemp ($160 million), Jacoby Ellsbury ($153 million) and Carl Crawford ($142 million) have received.

In the current market, Upton is worth something along the lines of a $20-23 million average annual value. Despite being older, Jeff Todd of MLB Trade Rumors predicted during the winter meetings that Cespedes would receive around the top end of that range, at $140 million over six years.

FanGraphs’ Dave Cameron predicted Cespedes would get $150 million over seven years. That total monetary value seems accurate, considering he is 30 and his recent and projected production, according to Cameron’s FanGraphs teammate Craig Edwards.

Cespedes has proven to be a power hitter with plus defensive value, and his value spiked last season during a six-week span with the New York Mets when he batted .309/.356/.691 with a 1.048 OPS, 10 doubles and 17 home runs. That red-hot stretch sparked premature MVP consideration and had Cespedes looking like he might be the best bat on the market this offseason.

Unfortunately for his stock, he cooled in the final two weeks of the regular season and was mostly unproductive in the postseason. In a free-market system prone to overreactions based on October performances, it was a bad time for Cespedes to go cold.

Now teams will value him properly, and that means $150 million, or its surrounding areas, is where Cespedes’ eventual price should end up residing, and probably for six years. That would be reasonable based on his history and projections, especially if he finds himself in an extreme hitter’s park like Baltimore’s Camden Yards—the Orioles have had recent contact with Cespedes (per Buster Olney of ESPN), but nothing serious has come of it yet:

Heyward’s contract is a decent barometer, and if more teams were involved in the Upton/Cespedes rumors, whoever signed second could use the other’s deal as more leverage—they both have qualities the other does not, which could be used in negotiations. However, the fact that the market seems small for both, and Gordon, could lead to one of them jumping on a deal, as the other is not necessarily assured to top it afterward.

While we can somewhat gauge for how much Upton and Cespedes might sign, the more intriguing part of this is which club will lock down one of them first. The outfield market has yet to truly open up, and that could end up leading to a race to the negotiating table before the money and options dry up.


All quotes, unless otherwise specified, have been acquired firsthand by Anthony Witrado. Follow Anthony on Twitter @awitrado and talk baseball here.

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