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Cardinals could benefit from slow outfield market: Sign Justin Upton?

Since Jason Heyward signed with the Cubs, the outfield market has moved slowly. Justin Upton is the best outfielder available. Could the Cardinals take advantage?

Jake Roth-USA TODAY Sports

Jason Heyward set the bar for outfield contracts this winter with his 8-year, $184 million contract with a first opt-out after three years that could potentially guarantee him $26 million per year during those first three seasons. Since that time, the outfield market has yet to develop. While pitchers, including Mike Leake, have flown off the board of available free agents, outfielders, and first base including Chris Davis, remain plentiful. While John Mozeliak previously ruled out a "dynamic" outfield signing, the market could be coming back to a level the Cardinals might feel more comfortable with.

Consider the following outfielders (and Davis) after Heyward, per the FanGraphs crowdsourcing project at the beginning of the offseason (median years, dollars):

  • Yoenis Cespedes: 6/$132 M, unsigned
  • Justin Upton: 6/$120 M, unsigned
  • Chris Davis: 5/$100 M, unsigned
  • Alex Gordon: 5/$90 M, signed with Royals for 4/$72 M
  • Dexter Fowler: 4/$56 M, unsigned
  • Denard Span: 3/$36 M, signed with Giants for 3/$31 M
  • Austin Jackson: 3/$30 M, unsigned
  • Gerardo Parra: 3/$24 M, unsigned
Not all of the above players make sense for the Cardinals. Right now the Cardinals project Matt Holliday for left field, Randal Grichuk and Tommy Pham in center field, and Stephen Piscotty in right field with Brandon Moss available in the outfield and at first base along with Matt Adams. In some combination, those players should be able to provide roughly average production at all four positions. For the Cardinals, that means that any player signed would have to provide a significant upgrade at some position to be of benefit.

Consider the Cardinals corner outfield and first base situation at present. There are currently 2100 plate appearances to divide between Stephen Piscotty, Matt Holliday, Brandon Moss, and Matt Adams. Let's assume no injuries and we give 600 plate appearances to Matt Holliday and 600 plate appearances to an outside acquisition. That leaves 900 plate appearances for Piscotty, Moss, and Adams. Regardless of how they divide them up, each player should have the opportunity to prove himself and no player will have his development hindered, particularly in Piscotty's case.

The Denard Span signing by the Giants looks to be a good one because he provides an upgrade over their incumbent options, but the same would not necessarily be true for the Cardinals. The same holds true for the other mid-tier options like Fowler, Jackson, and Parra. Gordon's signing with the Royals appears to be a good value, and while a deal like that might have made sense for the Cardinals, going an extra year and giving up a draft pick for a player into his 30s is a defensible position.

Chris Davis is an interesting player, but the Orioles "stand by" their seven-year $150 million offer to Davis. Davis might be shopping around for a better deal, but the Orioles preference appears to be keeping Davis, holding up any deal for an outfielder. Ultimately, Davis is likely to either get a better offer elsewhere or sign with the Orioles for an amount he not likely to be worth, keeping his market high and out of the range of the Cardinals.

As for Yoenis Cespedes and Justin Upton, I wrote last month the Cardinals should not spend just because they can, and attached dollar figures at which I would be interested:
The Cardinals have a ton of money, but that does not mean they should waste it, or spend top dollar on marginal increases. There is a dollar value where I would take Upton, Davis, Cespedes (who has expressed a willingness to play right field in the past), or Gordon (maybe $80 M for Gordon, $100 M for Davis or Cespedes, and $120 for Upton), but unless the market drops, those players are unlikely to be decent values.
We already saw Gordon go for under $80 million, and Davis is not likely to drop to $100 million, but we don't yet know where Cespedes and Upton will land. One important factor for the Cardinals is the draft pick compensation for signing a free agent. The Cardinals have three picks in the early going of the draft: their first round pick, and picks just after the first round for Jason Heyward and John Lackey. Yoenis Cespedes does not come with a pick attached due to his midseason trade, but Justin Upton does.

While the draft pick compensation is important, Upton is the better bet to provide value over a long term contract given his youth and consistency. Derrick Goold recently wrote about the possibility of a pillow contract, a one-year deal that would allow Upton to hit the free agent market at Age-29 when there will not be a glut of outfielders available and Upton could opt to go the one-year route. He discusses several scenarios, and the entire article is worth reading, but he makes a very good point about offering Upton a one-year deal, and hoping to get a draft pick for him after next year if he left for free agency.
A team could sign a QO'd player this winter to a one-year deal, slap that player with a QO next winter, and both parties bank on benefitting a year from now. The outfielder gets the multi-year windfall he couldn't in this market, and the team gets that pick back, just for 2017. This is reasonable. The subtle catch is this: The current Collective Bargaining Agreement that governs these things - the qualifying offers, the draft, the draft bonus limits - expires this year. Negotiations between Major League Baseball and the players' union are set to take place throughout this year, and one of the things that the union wants addressed is ... qualifying offers. The CBA expires on Dec. 1, 2016, so just after the deadlines for such things as qualifying offers. It would take an early agreement, one sliding into place ahead of the next offseason. But, there could be new directions in place.
Upton at six-years and $120 million might be out of the Cardinals' price range, but any lower than that, and it is a deal worth considering, if not jumping on. A five-year deal would cover ages 28-32, and while an opt-out in a longer deal would not likely be worth the risk for a solid, but not great player, an opt-out after one or two years when the money left to pay would not hamstring the organization should be a consideration. On a one-year deal, it is hard to imagine any team not wanting Upton, although given the difficult of hitting home runs in St. Louis, the Cardinals might not fit what Upton is seeking.

This could all be rendered moot by the so-called "mystery team", but right now there are a lot of outfielders and few apparent suitors. A drop in price could make a few of these outfielders fall in the Cardinals' range. Right now, it still appears unlikely that the Cardinals get involved, but Justin Upton should be an option for the Cardinals if his price really does fall.