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Yankees Mailbag: Early extensions, Judge’s historic comparisons, and the bullpen

The mailbag is back to answer more of your thoughts on the team’s future and Aaron Judge’s masterpiece season.

Boston Red Sox v New York Yankees Photo by Sarah Stier/Getty Images

Good afternoon everyone, it’s time for another edition of the mailbag. Remember to send in your questions for our weekly call by e-mail to pinstripealleyblog [at] gmail [dot] com.

Darth_Lazarus asks: Seeing more teams starting to lock up young stars right away (Acuña, Franco, etc) is there any reason why the Yankees don’t? Financially speaking, given inflation and demand, contracts only get more expensive. For example, they could’ve offered judge a 10 year after 2017 and it would likely cost less than the offer he just rejected AND would’ve ended around his 36-37 years.

It’s not that the Yankees don’t do this, but that they tried to and managed to pick the worst possible extensions. Luis Severino and Aaron Hicks both received long-term extensions within short succession of each other, but immediately injuries (and in Hicks’ case, lack of production as well) sunk those contracts. From there, with the understanding that the team wanted to play around the luxury tax as much as possible with intentional resets coming every few years, it became harder to envision those long-term deals, especially when the Yankees needed an ace and paid top dollar for Gerrit Cole.

It also takes a willingness from the player to take the sure thing rather than betting on himself, like Judge did this season — Atlanta has been fortunate to sign some immensely team-favorable deals that everyone in the industry knew would favor them the moment they were signed, so while they’re the most aggressive team in terms of extending their players they’re also not exactly a model that can be followed. The Yankees have a young group of top prospects rising through the system that they seem to be betting on immediately plugging into the team once they’re ready, so we’ll see if they approach players like Volpe and Domínguez with these types of offers if/when they make it to the show.

The idiot that said, “Harper is coming” asks: How will this season rank among all-time great offensive seasons if Judge completes the triple crown AND hits number 62? Overall offense is down this year, and he’s hit 20 more home runs than the next closest batter. It has to be up there in the top three or four seasons.

We talked about this in a Spaces conversation earlier in the week, but for many of us this is the greatest offensive season we’ve ever witnessed live, and it will certainly rank up there with some of the greats. There’s a very real chance that when the final numbers come in, you could argue that Judge is playing one of, if not the greatest non-Bonds seasons a hitter has completed. There’s not much else to compare to what he’s doing right now, and it’s something to marvel at even as we’ve watched close to 150 games of it already.

Neil S. asks: The Yankees have a lot of guys in the bullpen who could theoretically make the postseason roster. Who makes it? Who is left off the roster? Among those who make it, who is in the high leverage tier, the middle relief tier, the low leverage tier, or whatever tiers you guys have for organizing the bullpen?

When I ran through the likely playoff roster a month ago, we laid out a lot of the groundwork for the bullpen here. A bit has changed since then with the position players making a bit of a shuffle thanks to injuries and the emergence of Oswaldo Cabrera, but on the pitching side not much has changed in terms of who should make it. In terms of who is in the circle of trust, however, a lot has happened.

On the positive side, Jonathan Loáisiga has made me a believer again and Zack Britton indeed has gotten healthy enough to make it back to the team with a couple of weeks to spare. On the other hand, Clay Holmes has not gotten into enough of a groove to completely trust him, Aroldis Chapman missed a bunch of time due to a foolish mistake, Scott Effross also got hurt and was shut down for a while, and Wandy Peralta just went down as Britton returned. The bullpen is in a massive state of flux, with no clear top end and bottom end at the moment — Holmes has defaulted back to the closer’s role, but the confidence isn’t the same as All-Star break Holmes, and the core veteran relievers that could back him up haven’t been in game-shape for long. These last two weeks will be crucial to figuring out who are the names Aaron Boone can pull out in a jam when a single game can decide your entire season.

DFAHickinstead asks: When will the Astros return to being a team that tanks to replenish their system? Or are those days gone for good? Shouldn’t their window eventually close? And who do you see taking over as the Yanks’ No. 1 thorn in their side? Toronto?

I don’t think the Astros will be that bad again for a long while, as they’ve shown a solid ability to bolster their core and replenish it even with some of their original centerpieces leaving in free agency. Even though George Springer has still been excellent in Toronto and Carlos Correa left for a short-term deal in Minnesota, Houston’s offense has still been one of the best in the league. Jeremy Peña has been a suitable replacement at shortstop, and even though the Astros don’t have quite as good of an answer for center field the rest of the lineup more than covers that.

Even looking back to when the Astros watched Gerrit Cole leave in free agency, they’ve been buoyed by Justin Verlander’s continued excellence when healthy. Even when they didn’t have him due to Tommy John surgery the last two years, the rotation featured two solid arms in Lance McCullers Jr. and Framber Valdez, so Father Time won’t decimate them when Verlander finally realizes his age. The Astros have made it to five consecutive ALCS and three of the last five World Series — that isn’t fleeting success or luck, that’s a franchise that is loaded with talent. The Yankees have known for quite some time that they’d have to exorcise their demons if they want to make it far this year, but it also remains true for being contenders into the future as well.