The Value of the “Pillow Contract” for Justin Upton

In an offseason in which spending has been huge, perhaps even at an all time high, there hasn’t been much talk of money being an issue. However, as it pertains to a couple of players, the market appears to be drying up, or at the very least, quieter than expected.

For no player is that more true than Justin Upton. Going into the offseason, after another strong season playing for the San Diego Padres, the sky appeared to be the limit for Upton’s next contract. It was unclear if Upton could garner the same sort of contract as a player like Jason Heyward, but Upton was still a solid, above average player entering the prime of his career in a contract year. At the beginning of the offseason, there was talks of a six- or seven-year contract exceeding $150 million.

Already ten days into January, those predictions seem like they came ages ago. Apparently, with the market appearing quiet, the Chicago White Sox and Los Angeles Angels have already offered Upton cheaper, short-term contracts. At this point, it seems unlikely that Upton will get the big-money contract that was discussed earlier in the offseason. With that being said, would Justin Upton be willing to take a one-year “pillow contract?”

First off, for those who do not know, the phrase “pillow contract” refers to a short-term, usually one-year, “show me” contract for a veteran player between longer term deals. This has been used in the past for players who had a down year, and signed a lesser contract to prove themselves on a one year deal before trying again for a long-term deal. This type of contract could also come into play in the scenario with Justin Upton. However, there is one issue with Justin Upton signing this sort of one-year “pillow contract.”

According to Upton’s own agent Larry Reynolds, they are not considering shorter term deals at this time, and appear to still be waiting it out for a longer term deal. With the market seemingly drying up, it may be prudent for Upton to take a shorter term deal. Taking a one year deal could be a good decision for Upton and his representation for a variety of reasons.

This takes us back to the value of a pillow contract, as the title says. For Upton, if he agrees to take a one-year deal rather than a big, long-term contract, he can probably demand somewhere in the $20-25 million range for a one year deal. With such a weak free-agent market after next season, with Colby Rasmus, Carlos Gomez and Jose Bautista being the best outfielders on the market, Upton could get the long-term contract he desires next offseason, when he will still only be 29 years old. He will clearly be the youngest option, and also the most successful of any of the free agents available.

So Upton can take a one-year contract, take home a not insignificant sum of money for next season, and then once again enter the market and get his long-term deal. As good as it sounds, this strategy does come with its downsides.

First off, Upton could get injured next season, torpedoing his value to a new low. Going off of that, Upton could have a down year next year, which would probably get him less money next offseason than he could get this offseason. Finally, it may be unclear what team is willing to give up their first round draft pick for a player who will only be with the team for one year. However, next offseason that team can offer Upton a qualifying offer, thus garnering the team a pick as compensation. Therefore the team would lose a pick in this year’s draft but potentially gain that pick back a year later. One caveat to this argument is that one of the top potential suitors for Upton, the Chicago White Sox, have a protected first round pick and thus would only have to give up their second round pick for Upton. If Upton is going to go the route of the pillow contract, he needs to put himself in the right setting. The White Sox offer a smallish ballpark and a division filled with middling pitching staffs. Same goes for the Baltimore Orioles. Signing with the Angels would give Upton the chance to produce with very little pressure.

As it pertains to the free agency of Justin Upton, there are pros and cons for him taking a one year “pillow contract.” The contract definitely has some value, with the weak free agent market of next offseason. However, the contract does come with some risk, if Upton performs poorly or gets injured next season. It may be unlikely, but it is not something that Upton and his representation should write off so quickly. A one-year contract could be the best deal for Upton this offseason.

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