Should the Yankees be interested in any prospect extensions?

Baseball is a game of following trends and adapting to new methods. Managing the future of a team’s prospects is no different from the on-field decision making, as there are several ways to prepare for the next breakout star.

The most recent—and controversial—strategy involving top prospects was the manipulation of their service time, only calling them up to the majors after an extra year of team control was secured. While beneficial to the team’s finances, it came at the cost of potentially angering the player and damaging relations down the line. The Chicago Cubs are still dealing with the fallout from their handling of star third baseman Kris Bryant’s call-up in 2015, and may trade him before all is said and done.

The Yankees are not innocent in this regard, as they handled the call-up of Gleyber Torres in a similar matter, but had the coincidental timing of health concerns to cover it over. A new trend is emerging however, that could be seen as a compromise between teams desiring control of rookie contracts and players wanting financial stability before they enter free agency.

Clubs are beginning to sign breakout players to contract extensions before they ever don a major-league uniform. Five players have agreed to deals of this nature, four of which came in the past two years: the Phillies’ Scott Kingery, the White Sox’ Eloy Jimenez and Luis Robert, and the Mariners’ Evan White. The structure of all of these contracts are similar: the player is guaranteed a contract of six years that pays them somewhere in the range of $20-$50 million, and then includes club option years tacked on.

The deals are struck to give players that the team wants starting the year on the major-league roster an upfront pay, respective of their talent, while ensuring that they’ll be in that club’s uniforms for a long time. They avoid the messy areas of dealing with service time manipulation and arbitration talks, but also almost guarantee that the player won’t reach free agency until they’re on the other side of age 30. That’s a fair amount of risk on both sides, which explains why we haven’t seen too many of these deals yet, but they carry a large amount of upside if negotiated with significant prospects exclusively.

You’ll notice that the Yankees weren’t one of those teams to test the waters yet, and for good reason. The teams that have bet on their prospects so far have been rebuilding teams with roster space and some level of financial flexibility. The Yankees are a championship contender with a full major-league roster, and little room on the payroll to this point after agreeing to a massive deal for Gerrit Cole. There’s an opportunity for them to try it soon, however.

Several key contracts will come off of the books after 2020, including Jacoby Ellsbury’s ill-fated deal, Brett Gardner’s one-year swan song, the final year of Masahiro Tanaka’s contract and James Paxton’s final arbitration year. There is the potential for Tanaka and Paxton to return, but the option is available to spend some of the cash that’s freed up on a promising prospect.

The optimal comparison for the Yankees to the recent signees is Deivi Garcia. Garcia is the top prospect in the system (aside from Jasson Dominguez who isn’t close enough to the majors to consider yet) and flew through multiple levels of the minors last year. Garcia did struggle in Triple-A Scranton at the end of the year, but a bounce-back 2020 would all but seal his candidacy. Garcia could fill-in a spot in the rotation if the Yankees can’t manage to bring back everyone in the offseason, or complete it if Tanaka and Paxton do return.

The only complexity in this scenario is that the template so far has only been used on position players, who are easier to project into the majors if they rise through the system quickly. The same can’t be said for pitchers, so Garica might be the milestone case for 2021. The Yankees do have another ranked prospect in Estevan Florial that could fit the mold, but Florial has struggled at rising to the top of the minors like the others have. This could prove a breakout season for him, but his history may suggest that the Yankees would rely on the traditional model instead.

Dominguez, despite his age, is the type of prospect best suited to this discussion, but even with a fantastic 2020 there’s simply no feasible way that he gets close enough to the majors in one year. Afterwards, it becomes too difficult to project what the Yankees’ situation looks like financially for when he’s expected to reach the big-league club. There’s no doubt that The Martian is a big part of the Yankees’ future plans, but he’s more likely to be the beneficiary of this system succeeding already than one of it’s first trials.