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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.

torturedsoulv1 asks: How many relievers do you think the Yankees need? How many do you think they will actually trade for?

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They could probably use a couple, if we’re being honest, but they’ll swing for at least one. Camilo Doval has all the tools to be a quality reliever and yet has utilized them to be supremely frustrating since arriving over from San Francisco at last year’s deadline. He’s the most likely candidate to get jettisoned off the roster in a bullpen shakeup, as I just can’t see the team trusting him with late leads down the stretch and they have more effective pitchers for mopup duty. Jake Bird started off looking like a lost cause but has turned things around in May and June, so he’s got a place for now though he also has an option remaining if the team wants to stash him back down in the minors in case he runs into another stretch of looking unplayable. Tim Hill has also seemingly lost some of the magic of his lanky lefty ways, so if they could find an effective left-handed upgrade they might take it, but he’s not pitching as bad as he was during a terrible May anymore.

Up until yesterday, I would’ve said the plan was to look for said lefty as a trade acquisition and rely on Carlos Lagrange as the right-handed upgrade, but now that he’s on the IL with a shoulder injury I think that shuts the door on a 2026 debut for him even in a relief role. It’s more possible now that they push for two arms, especially given their apparent reluctance to trust Yovanny Cruz with a role in this bullpen despite his success in the few outings he’s gotten, but perhaps Cruz slots into the spot they intended for Lagrange instead once he’s allowed back up to the majors.

OLDY MOLDY asks: Will there be any real impact bats available at the trade deadline?

The most impactful one for the Yankees would be Minnesota’s Ryan Jeffers, whom the Yankees could help push towards being sellers by waking up and beating thoroughly this weekend. Though he’s only played in 37 games this season because of a hamate injury, Jeffers was posting a career-best season before he got shelved and is close to a return after hitting for consecutive days. His 164 wRC+ would blow the rest of the Yankees’ catchers out of the water, and he’s had enough success as an above-average hitter over the last three seasons to warrant belief that he’ll provide some thump to a position that has desperately needed even close to average production. Austin Wells at this point has been in the doldrums long enough to believe that his bat just isn’t going to come around, even if he does pull out of the simply miserable run he’s been on this year, and Jeffers’ defense is solid enough to warrant significant playing time down the stretch. Since he’s on his last year of arbitration as well, it shouldn’t be too costly to rent what is the ideal addition to an offense that desperately needs some help.

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The idiot that said, “Harper is coming” asks: Now that we’re more than halfway through the 2026 season, what does Jazz Chisholm Jr.’s offseason look like if his current level of play continues? He’s currently slightly below league average offensively, and by some metrics below average defensively at his best defensive position. Do the Yankees extend the qualifying offer to him? If so, does he take it?

Jazz has had a fascinating year — not a good one, but a fascinating one. It’s entirely possible that he goes on a second-half run like Gleyber Torres did in 2024 to recoup some of the value he’s lost over the first 80-plus games played, but as of right now if the qualifying offer came his way I’d have to assume he takes it and tries again on the open market with hopes of a rebound year establishing his numbers as a Yankee as the expectation for whoever signs him. Should the Yankees extend that offer to him, though?

They offered it to Trent Grisham last offseason, and by all reports were surprised when Grisham actually ended up accepting the deal. That may have led to their offseason plans changing, though with the benefit of hindsight I’m not sure if they were ever really going to be that invested in the Kyle Tucker Sweepstakes which meant that Cody Bellinger’s return was always the top goal and Grisham’s return obviously didn’t impede that. What it did mean was that their playbook was more restricted, and with Bellinger asking for more money than they thought reasonable that led to a significantly drawn-out winter. This time around I’d have to assume they’d be more aware of the possibility of Chisholm accepting, and in fact a qualifying offer might be the only way that Jazz sticks around another year in pinstripes if his asking price isn’t completely deflated.

The 2026 class of free agents don’t look to have any game-changing targets at positions of need for New York, and while there may be interest in renting Tarik Skubal’s services I doubt they’ll wade into the bidding war for his long-term contract so the money’s there to gamble on one more year with Chisholm should the team want to. Add onto that the impending lockout hanging over the sport, and a short commitment that would avoid scrambling to put together the team if/when baseball is played in 2027 doesn’t sound like a bad idea.

BetweenthePinstripes asks: Are the Yankees ever going to win again?

Eventually, friend.

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