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Signed OF-R Justin Upton to a six-year deal worth $132.75 million, with an opt-out after 2017.

Over the past week or two, as the free agencies of Justin Upton, Yoenis Cespedes and Chris Davis stretched improbably toward spring training, there were rumors that one or more of those players might end up settling for a one- or two-year deal. The theory was that, with the leverage of the ticking clock on their sides, teams might be able to convince someone (most likely Upton or Cespedes) to take a short deal aimed at reestablishing value and landing on a less crowded, less encumbered (by the ugly terms of the current CBA) free agent market not far down the road.

As it turned out, Upton was the one who took that sort of deal. He just happened to secure a four-year player option, at the end of his two-year pact with the Tigers. A four-year option is a risk, of course; it would have been nice to have more than one chance to choose between guaranteed money and the marketplace. Jason Heyward, two years Upton’s junior and with a bit more well-rounded a skill set, got two such options. Still, it’s there. Upton will be a Tiger for two years, after which time he’ll still be on the right side of 30 and should face fewer impediments to getting the full value of his skills on the market. If something goes wrong in the interim, though, he also has a handsome insurance policy in hand.

From the Tigers’ perspective, a four-year option is a hell of a thing to hand out, but it’s a risk worth taking. Upton almost assures them of surpassing the luxury-tax threshold in 2016, a first for them. Since he’s likely to come off the books after 2017, though, and since we all anticipate the threshold and the rules for luxury-tax spending to change substantially in the new CBA that will be hammered out sometime this year, that’s a fairly small concern. Also, handing out such a hefty option effectively makes the contract a six-year deal, for luxury-tax purposes. Since luxury tax calculations are done using the annual average value of multi-year deals, the Tigers will only have Upton count for $22.125 million per year against them while he’s around. If they’d given him any fewer than those four years, he’d have demanded a higher annual average, which would have (in turn) increased their luxury-tax bill and complicated any efforts to stay under the new threshold in future seasons.

We won’t know the specific calculus until the annual salary breakdowns come out, but for now, it looks like the Tigers are hoping Upton will pass up his player option, and that this will truly shake out as a two-year deal. If it does, it fits them perfectly. Justin Verlander, Victor Martinez, and Miguel Cabrera have, at most, two more good years in them. The same is probably also true of Ian Kinsler and Anibal Sanchez, both of whom will hit free agency after 2017 anyway, unless the team exercises its club options on one or both. J.D. Martinez is young enough to have plenty of good baseball left in front of him, but he’ll be a free agent after 2017, unless he signs a long-term extension first. This core has two more very good years of sunlight in which to make hay, and Upton’s two certain seasons of team control (at ages 28 and 29) could not possibly line up better with them. In fact, though it would have been nice to get the left-handed lineup balance offered by Heyward, Davis, or Alex Gordon, it’s possible that no free agent better fit the Tigers’ positional needs than did Upton.

He certainly won’t fix the Tigers’ shaky outfield defense; that’s probably Upton’s greatest weakness. On the other hand, he hits for power, controls the strike zone well enough to tap into that power very consistently, and is a good baserunner. With Upton mixing somewhere into the cluster of Kinsler, Cabrera, Martinez, and Martinez, the Tigers now have the best five-batter sequence in any AL Central lineup, and their supporting cast might be as strong as any division rival’s, too. Upton had a .294 TAv in 2015, an exact match to his career mark. The only hitters who topped that figure in 500 or more plate appearances for AL Central teams in 2015 were Cabrera, J.D. Martinez, and Lorenzo Cain.

Upton is a really nice capstone to a really nice offseason of reshaping and reloading, by a rookie GM. Al Avila has deepened Detroit’s pitching staff from top to bottom, found a solid insurance policy and platoon partner for Anthony Gose in center field, and now fattened the middle of his batting order, to boot. The Tigers really might be the AL Central favorites, at this point.

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A very nice write up.

This also helps the lineup because instead of Maybin and Gose everyday in left and center, they now platoon in Center.

Regarding the Luxury tax, projections had them right at the threshold BEFORE the deal was signed, so they're absolutely paying Lux tax on every dime of it this year, what happens after that, though, depends on what comes out of the CBA, as the author points out, and I would be surprised if the lux tax survives that negotiation, and if it does it will be drastically reduced.

Expect an extension shortly on JD Martinez... offering him $2m under MBTR projections when he's settling for said projection, after they paid a combined $2M over projection to avoid arbitration with 3 lesser players, is directly opposite from how this team does business, I suspect negotiations on said deal are already underway, delayed because Al Avila was busy negotiation the Upton deal.

Most surprising, Ilitch cracked the pizza piggy bank, not for the guy he had a history with, but the guy who, as the author points out, was a better fit.

A technical questions: is there time before "The Book" has to go to press, to include this deal in the overall analysis?
Unfortunately no, because fortunately the book is already gone and printing and should be out in not long.
Also worth pointing out that signing arguably the best free agent hitter in this year's class costs the Tigers... a 3rd round pick.
"Upton will be a Tiger for two years, after which time he’ll still be on the right side of 30 and should face fewer impediments to getting the full value of his skills on the market."

As long as you don't consider Josh Donaldson, Bryce Harper, Andrew McCutchen, and A.J. Pollack impediments. These four representing the potential free agent outfielder class of 2018, as recounted elsewhere on this site.
Donaldson is a third baseman, and a pretty good one too.
Upton would be a FA after the 2017 season if he declines the option.
"As long as you don't consider Josh Donaldson, Bryce Harper, Andrew McCutchen, and A.J. Pollack impediments"

four guys, 30 teams.

Granted not all 30 will be in the market and/or looking for OFs but I still like his odds, especially since I don't think Harper and McCutchen will be let go by their respective team.

There were a lot of previous articles pointing out the opt out clause was a "Heads I win, tails you lose" deal in the players' favor, but Trueblood points out the appeal for the teams, it allows them to game the luxury tax rules.
And if Harper or McCutcheon does move on, then their old teams will be looking to score an OF of some consequence to replace them.