The Yankees have won three games in a row, but they can’t fool us. They’re still no better than the third-best team in their division, and our Playoff Odds Report gives them a seven percent chance of reaching at least the Wild Card Game. There’s no question that this team needs to sell at the deadline, and the charade the team’s front office and ownership group are conducting through the tabloids in New York is just that. They’ll trade Carlos Beltran and Aroldis Chapman this month. It’s just a matter of time.

For my money, though, the team shouldn’t stop there. Andrew Miller is the hottest name on the trade market, but only because it’s so non-controversial to suggest that an elite relief pitcher on a bad team be traded. The Yankees should trade Miller, but they shouldn’t stop there, either. The next good Yankees team, at this moment, is three or four years away. The market is shaping up perfectly, though, to allow Brian Cashman to shorten that term of mediocrity, to push the pedal to the floor and speed his team back to the brink of contention—with an organization full of young talent, this time.

Here’s the gist of my argument:

1. The Yankees should and do have their eyes on the potential free-agent class of 2018-19. To spend freely there, though, they need to get under the luxury-tax threshold in one of the next two seasons. The current rules around the luxury tax involve significantly heavier penalties for repeat, consecutive crossers of the threshold. The rules could change under the new CBA that will take effect this winter, but they don’t figure to change direction in this regard.

2. Whatever they spend, the Yankees can’t win the AL East this season, and they won't win it next season. Beyond that, it’s impossible to say for sure what will happen, because this is baseball, but the old, broken, inflexible roster the Yankees have right now isn’t going to miraculously overcome the Red Sox and Blue Jays any time soon.

3. If the goal of the Yankee brass is to build a new dynasty, something along the lines of the Jeter-Rivera-Williams-Posada-Pettitte team, they’re going to need to tear the team down to the studs and rebuild. As I’ve written before (regarding the Cubs, who just blazed this very trail), the rule set that governs team building doesn’t permit the kind of shifting resource allocation the Red Sox used a decade ago to compete and spend big even while loading up the farm system. The path to greatness is paved with pain, and all signs point toward that becoming even more true under the coming CBA (even as league officials and media members wring their hands about teams’ responses to the rules).

In addition to Beltran, Chapman, and Miller, the Yankees have at least six valuable players with significant trade value: Dellin Betances, Brett Gardner, Didi Gregorius, Brian McCann, Michael Pineda, and Masahiro Tanaka. Betances might have more utility as a trade chip than as an actual Yankee, by the time the team is good again, but it’s too early to make that deal this summer. The same is true for Gregorius. The other four, though, are already being paid hefty salaries, and will either reach free agency or decline significantly before the Yankees are good again. That doesn’t mean the Yankees should trade them all, and it’s certainly not the case that they should trade them all this month. However, at least two of the four should change teams before the deadline.

Both Tanaka and Pineda can be free agents after 2017. (Tanaka could opt out at that point, or elect to play out the rest of his contract (for $67 million through 2020. Pineda will be a free agent based on service time.) They’re solid starting pitchers who could start a playoff game for many teams, and who would substantially increase the chances of getting to the playoffs in 2017 for whichever team they might join. In this summer’s pitching market, where buyers (Cubs, Dodgers, Rangers, Marlins, Orioles, Astros, maybe Pirates, maybe Giants, maybe Tigers, maybe Royals, maybe still Red Sox) outnumber sellers, either guy could net the Yankees some really good young talent. McCann would be the second-best catcher available (after Milwaukee’s Jonathan Lucroy), with at least a few contenders (Indians, Rangers, maybe Tigers, maybe Dodgers, maybe Mariners) looking for one. Gardner would, at the very least, draw the interest of every team with an outfield weakness, but the presence of several other outfielders on the market could soften the demand for Gardner.

Deep forays into the international free agent market have helped the Yankees put together some impact minor-league depth. They can also add a capstone or two with a high draft slot next summer. Still, they could seriously accelerate their return to the kind of team at the core of their brand by trading away some veterans, gearing up to spend bigger and more freely in a few years, and gathering up some prospect talent that would have seemed inaccessible just a year ago.

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If the Yankees could only be about building the next great team this could work. I suspect that Steinbrenner is not willing to deal with his fan base should the Yankees go from average/average-minus to bad or awful. Taking the fastest route to the next flag does not mean that all paths there are acceptable to the team as a matter of the business necessities of fan tolerance for the team.
I agree with Matthew, but I don't see Hal signing off on anything other than Schwarber for Miller, which would never happen.
I don't disagree with your logic but this sounds like a strategy approximately 20 teams in the MLB should/will have for 2019, not just the Yankees.

I agree with all but Didi, even though Tanaka trade gives me pause.