Operation 2019: Inside the Yankees’ Plan

Finally, the Yankees’ long-term strategy is abundantly clear. Brian Cashman’s approach to the Winter Meetings proved he is serious about not spending on elite free agents at this time, and shifted his rebuild into public view. The Yankees appear to be focused on the distant future and, while it will be disconcerting to see them take a sabbatical from the major market, there’s something cathartic about The Plan being revealed.

By moving Justin Wilson for two fringe prospects, and by shopping Andrew Miller and Brett Gardner, the Yankees revealed their emphasis on the future, rather than the present. Jacob Lindgren, a 22-year old strikeout machine, will move up the bullpen depth chart, as the team continues to refresh. Meanwhile, the acquisition of Starlin Castro gives the Yankees a super-talented second baseman, but also informs of the new philosophy on River Avenue, as the Bombers work to develop a core of young, athletic players with their best years ahead of them. Castro will form an exciting double-play tandem with Didi Gregorius, another cog in the new machine, while Greg Bird, Luis Severino, Aaron Judge and Gary Sanchez also fit the mould.

Thus, the Yankees are now emphatically devoted to the idea of regeneration while large contracts come off the books. It’s almost like Cashman and Hal Steinbrenner sat down following the retirement of legends such as Mariano Rivera and Derek Jeter, and plotted a new course for the franchise. Evidently, that course includes starting over once expensive veterans like Alex Rodriguez, Mark Teixeira and CC Sabathia have left, and also places significance on building a fresh team below the luxury tax threshold of $189 million.

Accordingly, Cashman looks to be working towards the 2019 season, when the only guaranteed contracts belong to Masahiro Tanaka, Jacoby Ellsbury and Castro. At that point, the aforementioned veterans, and their albatross contracts, will have left, along with Brian McCann, Carlos Beltran, Chase Headley and others. In the winter of 2018/19, the Yankees will, at long last, have an opportunity to start from scratch and adhere to a more sustainable model fit for the changing baseball environment.

Therefore, while many of Cashman’s current moves may not make total sense, they seem to be aimed at building a young core ready for 2019 and beyond. In four years time, Severino will be 25 and the presumed ace; Bird will be 27 and ensconced at first base; while Sanchez will also be 27 and likely the starting catcher. Similarly, Judge will be 27 and playing everyday; Jorge Mateo will be 24 and pushing Gregorius; and James Kaprielian, a first-round pick this year, will be a strong 25-year old starter. Ideally, this will provide a homegrown, cost-effective structure around which to construct a team for repeated contention.

But why 2019, I hear you ask? Well, because the 2018/19 free agent class could be the greatest of all-time, and one that will coincides nicely with the Yankees’ new core reaching its prime years. It will be the ideal time to supplement those cornerstone players with external upgrades, and here’s just a few who will be available, if extensions aren’t agreed and opt-outs are exercised:

  • Bryce Harper, age 26

  • Clayton Kershaw, 30

  • Jose Fernandez, 26

  • Matt Harvey, 29

  • Manny Machado, 26

  • Andrew McCutchen, 32

  • Josh Donaldson, 33

  • Dallas Keuchel, 30

  • David Price, 33

  • Adam Jones, 33

  • Michael Brantley, 31

Even factoring in likely arbitration expenditure and the desire to get below $189 million, the Yankees may have upward of $100 million in average annual salary to spend within that market, assuming they don’t add any long-term pieces in the next three years. That would allow them to perhaps sign three or four of the marquee players mentioned, and the prospect of adding prime-age stars like Bryce Harper, Manny Machado and Jose Fernandez to a spine of potentially elite performers such as Severino, Bird, Judge and Sanchez is tantalising.

A year later, following the 2020 season, Mike Trout may become the most prized free agent in history, and Giancarlo Stanton can also opt-out of his mega-deal with Miami. Both will be just 29-years old and, presumably, in their peak years. By exercising prudence in the short-term, the Yankees may be in the strongest position of all Major League teams to pounce on those once-in-a-lifetime assets, should they become available.

But right now, the Yankees won’t tear everything down and tank like the Cubs, Astros, Braves and Phillies have in recent years. That’s just not in their DNA. Yet, the basic premise is pretty much the same: de-congest of bad contracts while generating a fresh nucleus, then look to supplement via elite free agency to create a lengthy window of contention.

Rather than punt entire seasons between now and 2019, Cashman will try to swing trades that don’t damage the Yankees’ future, while staying out of the free agent market to protect draft picks and stockpile resources. He will aim to trade players overvalued by the current trends of Major League roster construction (Wilson, Adam Warren, John Ryan Murphy, for example), and receive low-risk, high-reward pieces like Nathan Eovaldi, Gregorius and Castro in return; young assets with plenty of upside who will have an opportunity to earn a place in the team’s future plans. If an elite player of the right age becomes available via trade or the international market, Cashman may consider a bigger move, but such a deal would have to be compatible with the retooling timeline.

The stated aim will still be to compete for the playoffs every year, as the fanbase demands, but realistically, the Yankee brass may be content to land in the 85-win range during this reconstruction and hope to secure a Wildcard berth or squeeze a division title. Though many fans will find this disappointing, the Yankees are likely hoping to replicate their 2015 season in ’16, ’17 and ’18, remaining in loose contention and staying close enough to perhaps ride their luck into a deep postseason run. All the while, their main focus will be 2019, and tinkering on a future monster.

Of course, this strategy isn’t without risk. Almost every free agent class looks great four or five years in advance, but extensions get signed, especially in this age of increased revenue-sharing and huge television rights deals. Even the Nationals may be able to afford an extension for a superstar like Harper, just as the small market Marlins gave $325 million to Giancarlo Stanton. However, the Yankees have the resources to construct backup plans on the fly, so contingencies should be in place. Nevertheless, in all likelihood, some amazing talent will be available on the free agent market just as the team’s core blooms to fruition, presenting an ideal opportunity to build another dynasty.

So, the next few years may be difficult for Yankee fans, as veterans age and prospects transition to front-line roles. But, ultimately, that short-term frustration may be worth it, so long as a genuine World Series-contending team is on the field in four or five years time.


One thought on “Operation 2019: Inside the Yankees’ Plan

  1. Pingback: Yankees Reach Historic Crossroads | The Pastime

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