Yankees Mailbag: The stretch run and Tucker's free agency

Yahoo

2 days ago

Good afternoon everyone, it's time to dive back into the mailbag and answer some of your questions. Remember to send in your questions for our weekly call by e-mail to pinstripealleyblog [at] gmail [dot] com.
ReadingYankee asks: I, for one am shocked by the Blue Jays current run of success. I did NOT see them even having a winning record this season. Based on the remaining schedule, can you give us an idea of the Yankees path to clinch a playoff spot, whether it is the unlikely path of clawing back the division, or sneaking in as the (current position) third Wild Card. And who would be most likely to falter in front of them to open up that path?
I've been shocked by their ascension as well — if there was a team I thought would challenge the Yankees this year it was the revamped Red Sox, but the Jays being above both of them has been a surprise. The Yankees have blown through every metric that could've pointed them towards a rebound, and look every bit the part of a team destined for a first-round exit at best. Their hold on the final Wild Card spot is narrow, sitting just a half-game above the Guardians entering today, and they're staring at a 6.5 game deficit in the division. The difference between the first and third Wild Card is a negligible 2.5 games, so if they ever decide to finally pull out of the tailspin they've been on for months now they could easily get into more comfortable positioning, but that requires them flipping the switch in a major way from how they've been playing.
A series win against the Twins is a decent start considering where they've been, but they need a lot more consistency before we can count that as anything other than clearing the lowest bar imaginable. The rest of their August is actually very favorable for them — matchups against St. Louis, Tampa Bay, Washington, and the White Sox could all boost them back into the black for this month, and a crucial matchup against the Red Sox lies sandwiched between them. They need to hit their stride here, because the first half of September will make or break them — they face a gauntlet run against the Astros, Blue Jays, Tigers, and Red Sox back-to-back-to-back-t0-back. If they're in decent shape for that stretch than anything's possible, but if they continue to float down before they even get there I'd say they're more likely to miss the dance outright than not.
jmack175 asks: I'm a big fan of the '08 offseason strategy that brought in CC/Tex/Burnett as opposed to the lower tier more budget approach signed to longer contracts to bring the AAV down… having said that, I am clamoring for Tucker next year, but hear a lot of fans saying that we should resign Grisham instead to a five-year deal for $17 million per year or so. This seems like the type of mediocrity move that Cashman would pull — a guy has a career year who has never had one before and Cash overpays him for the next 6 year or 7 years (see LeMahieu, DJ, and Hicks, Aaron).
It's a bit of wishful thinking to plan for an '08-09 offseason-saving free agency class to come around again — the Yankees had everything they needed fall into place then and had no reservations about dropping the money necessary to get it, which are two circumstances that rarely come up anymore let alone together. To compare situations, New York would need to pull off a Tucker/Bregman/Framber Valdez or Dylan Cease type of haul to land a similar remodeling, and aside from the fact that landing even one of those names would be big news these days there's just no way that Hal Steinbrenner and company will go that far. Tucker is the jewel of the class though, and the Yankees have interest just like most of the league does, so let's focus in on him and the current Yankee outfield.
The Yankees obviously have Aaron Judge penciled in for right field in 2026 and beyond, and currently deploy a trio of Jasson Domínguez, Cody Bellinger, and Trent Grisham for the remaining two spots. Domínguez is a mainstay assuming that the team doesn't involve him in offseason trade talks, which they've been adamant about avoiding up until this point, which leaves Bellinger and Grisham left for us to discuss when we break down how the outfield could evolve. Bellinger has been one of the team's best bats this year, looking closer to the All-Star caliber player he once was with the Dodgers even if he doesn't have his 2019 MVP form anymore. He'd be great to keep around, and his versatility with first base means that they could shift him there next year with Paul Goldschmidt's contract expiring should Bellinger opt-in to his 2026 player option or re-sign with the team.
Grisham meanwhile, has been enjoying a career year unlocked with more regular playing time covering every spot in the outfield grass whenever Aaron Boone wants to play him in a particular matchup or give his starters a rest day. He's been incredibly valuable to the team and deserving of a raise from the $5 million he's earning in his final arbitration year, but the question becomes how much will he earn and with who. If he's getting a deal around $17 million per year as suggested, much as I've liked him in pinstripes I don't think the Yankees should lock him down for that, especially not while Tucker is still on the market. If they lose out and pay him as a Plan B, I could at least see the reasoning there, but if he doesn't get too much traction I'd love to see a world where the Yankees swing for both: get Tucker as your offseason capstone, and keep Grisham around as the super outfielder providing depth and keeping the starters well-rested. It's highly unlikely that they want to spend the money for both, but there's plenty of reason to believe it would work if they did.