Buried Aaron Boone nugget hints he should've left Yankees four years ago

Yankees fans predisposed to spit constant venom at Aaron Boone probably won't like Ian O'Connor's preseason reflection column published Wednesday, but it's probably the most honest appraisal of his tenure you'll see.

As O'Connor notes, Boone is a good manager who veers towards "very good" on occasion, but that has been nowhere near good enough, especially as the Yankees' competitors payrolls spike and Boone's rosters continue to wilt under pressure, both literal and spiritual. He has been afforded more than enough chances, and probably should not be afforded anymore if the 2026 roster does not deliver on the promise of the franchise's premise. Tough. Not tough enough for some. But probably fair.

However, one detail stood out from the prose that took me aback at first blush.

According to O'Connor, Boone told him at the end of the 2021 season that he was ready to walk away and would've been at peace with leaving the team before the Yankees countered with a contract extension that reinforced his belief that he was supposed to stay.

Objectively, it's a healthy attitude to be confident in the work that you've done, and to be able to separate it from your life at home. But is it wrong to say that the Yankees could go for a little more dogged pursuit of perfection in Year 9? Just a little more blood, sweat and tears? Someone who's an ounce hungrier?

If you're in the "Boone is a disaster" camp, you'll never be swayed by sympathetic arguments. But if, like O'Connor, you're more in the "Boone is good, not great, and probably never will be" department, doesn't it sound like it's time for him to follow his own advice and prioritize his life as a father and husband?

Yankees manager Aaron Boone could've walked away happy after 2021 season (and probably should've?)

If the lack of a title really is eating at him, some additional urgency should be shown. Otherwise, it feels like his departure is past due.

It was actually after 2022 when the environment felt safest to cut bait on Boone. The Yankees had spent April, May and June playing at an historic pace, only to barely hold on to a 15+ game lead and be swept away by the Astros, minutes after Boone tried to motivate the team with clips of the Yankees' 2004 collapse at the hands of the Red Sox. It was the type of catastrophic ending that usually results in heads rolling (and felt like it would send Aaron Judge to San Francisco).

But the Yankees of the modern era prefer patience, and they definitely would rather a manager/coach/executive's contract expire into nothingness rather than be severed. No, 2021 was the time, when Gerrit Cole limped off the Fenway Park mound in a season defined by "They can't really lose that, can they? Wow, they just did" losses.

Boone ended that season content with his resumé and ready to return to family life — until the Yankees reinforced their faith in him, a gesture he couldn't say no to. But he should've.