How James Shields Could Now Maximize His Earnings

Well, this whole James Shields situation sure is bizarre.

Back in October, the FanGraphs Crowd collectively projected that Shields would be the fourth-highest-paid free agent of the winter, in line for something like a 5-year/$90M contract. And now, this week, Tony Blengino took a look around the league, found very few teams who both had available money and a need to add to the top of their rotation, and predicted that Shields would sign with the Giants for 4 years/$75M.

If Tony’s prediction comes to pass, Shields would be leaving more than just $15M on the table. The actual contracts received by other top-flight free agents have well outpaced the Crowd’s projections. Max Scherzer received $210M (or so) over seven years after being projected to receive $168M. Fellow mega-earners Jon Lester ($155M v. $132M), Pablo Sandoval ($95M v. $80M), and Russell Martin ($82M v. $56M) also saw very meaningful increases over their crowdsourced projections.

That’s a pretty big chunk of hypothetical money to leave on the table, for the sake of — well, I’m not totally sure: maybe Shields’ finicky pursuit of a just-right situation? While there have been rumbles here and there throughout the winter about such-and-such team being interested in pursuing Shields, we still know next to nothing about Shields’ own values and priorities for his new home, and we don’t know a lot about any concrete offers that may have been extended his way. This is the rare baseball story that has remained in near-total stasis for three-plus months.

If Shields simply wants to earn as much money as he possibly can with his next contract, it would seem that he missed his golden opportunity to do so earlier in the winter, when teams still had large chunks of their budget empty and unreserved. So here’s an idea as to what Shields might do now to earn the most money possible from his playing career. Please note that the speculations to follow are pure speculation, and have no basis on real-life news. (Which, said real-life news includes an MLBTradeRumors report that Shields could sign by the end of the week.) But this will not stop me from imagining:

What if James Shields waiting until a contending team lost a starter to Tommy John surgery in order to sign a contract? Furthermore — what if he signed a one-year contract at a significantly high per-year value and then entered the free agent market again in the winter of 2015, equipped with all the lessons learned from this winter’s awkward free agency?

It’s been established, over so many years and so many transactions, that teams who wish to trade for present-tense, veteran help must pay a significantly higher price if they trade in-season instead of during the offseason. I.e.: last July, the A’s had to give up prospect of great price Addison Russell in exchange for a year and a half of Jeff Samardzija and half a year of Jason Hammel. And then, this winter, the A’s traded away two arbitration years of Brandon Moss and received the non-blockbuster return of Joey Wendle, a sixth-round pick in 2012.

Isn’t this pre-dawn moment before Spring Training the very time in the baseball calendar when a player’s value to a proposed new team would be at its lowest? This is the one moment of the year when the best-laid plans actually still resemble best-laid plans. Offseason plans have been executed and thirty rosters sit, fully-formed, just waiting to outperform their projections.

In other words: the elbow tendons have not yet hit the fan.

Shields’ best negotiating tactic at this point may just be to use a team’s suddenly dire need to fill in a spot in the rotation against them. While speculating about individual injuries seems cruel, it would also be silly to think that the dreaded specter of T.J. won’t cast its shadow over the 2015 season — and, specifically, over the starting rotation of a contending team.

Here was the notable damage from 2014 (which is excluding star pitchers from down teams, like Matt Moore in Tampa Bay or Patrick Corbin in Arizona):

–Oakland A’s – Jarrod Parker succumbed to Tommy John on March 17 after 61 solid starts from 2012-13, his first two years in Oakland. Jesse Chavez filled in admirably, making 21 starts in 2014 after two previous starts in the whole of his big league career. Although it’s easy to automatically mentally exclude the A’s from pursuing any remotely pricey players, having a James Shields still around on the free agent market would have benefited the 2014 A’s, who paid a hard-to-quantify but undoubtedly major price for additional rotation help at the trade deadline. In hindsight, would the A’s rather have paid Shields $20M for one year and kept Russell around, or have things play out as they actually did? What if Shields cost $25M for one year?

–Miami Marlins – It would be supremely bold of Shields to wait past Spring Training and then into the season to wait to sign with a team, but the additional wait could make a desperate team even more desperate. Wunderkind Jose Fernandez pitched his last game of 2014 on May 9, and at that point, the Marlins had the third-best record in the NL (20-16), and also the third-best Pythagorean Win% (.567). In September, Mike looked at the Marlins’ performance and concluded that they very easily could have made the playoffs were Fernandez healthy. While the Marlins are, yes, the Marlins, and are unlikely to pay big for Shields in any season, their ultimately nondescript 2014 season is a real-life case tragedy in how damaging losing one’s ace can be.

–Atlanta Braves – This is probably the most instructive example for Shields, were he to try this high-risk gambit. It’s helpful to remember that the Braves of February 2014 were positioned mighty differently than these Braves of February 2015: by handing out extensions to players like Andrelton Simmons, Julio Tehran, and Freddie Freeman, it looked like the Braves were locking another NL East-dominating core into place for the foreseeable future. So, losing both Kris Medlen and Brandon Beachy to T.J. within one dark March week of each other meant a serious blow to the playoff hopes of a team that sincerely expected to make the playoffs. And thus, Ervin Santana was hastily signed, for one year and $14.1M.

This winter — his second consecutive venture into free agency — Santana signed with the Twins for 4 years/$55M (plus a $14M team option in 2019). Combine that with his Braves salary and Santana will earn $69.1M over five years. Before his first foray into free agency, the FanGraphs crowd predicted that he would receive a 3-year/$39.8M deal. At this point, following Santana’s path could be Shields’ most lucrative option.