The Playoff Bound Yanks... But Can They Win It All This Time?

The Yankees are officially playoff-bound. Pop the champagne, right? 

Well… not so fast. The real prize isn’t sneaking in through the Wild Card door like some bargain-bin shopper on Black Friday. No, this is the Yankees. The bar has always been — and should always be — the American League East crown. That’s the standard.

Last night’s walk-off — courtesy of none other than José Caballero (not the shortstop or the catcher who decided to clock in at the 9th inning) — gave us one of those “finally, some life” moments. And Boone, in classic Boone fashion, celebrated with: “Don’t take that s–t for granted. We are in the playoffs, we’ve got a lot more to do, right? We’ve got a lot of bigger goals. But enjoy this, celebrate this right now and come get ’em tomorrow.”

Great speech, champ. Almost convincing. But here’s the problem: the Yankees should already have this division wrapped up. The fact that they’re clawing back in September says less about the roster and more about a manager who insists on shoving square pegs into round lineup holes. Boone’s obsession with his “golden boy” Volpe at short has been the hill he’s willing to die on. And yet — it was Caballero who delivered the knockout blow. Irony loves the Bronx.

Meanwhile, Jazz Chisholm is out here talking like a man who gets it: “I feel like I’m very proud but I feel like I’d be prouder with a ring on my finger and saying that we won the World Series.” That’s the mentality. Forget just “getting in” — the mission is rings. Period.

Now, credit where it’s due: I didn’t think this team would even make October with Boone steering the ship. That’s on me. But here’s where I stand firm: this squad is too good to be a one-and-done. The question is whether Boone is capable of leading them deep. Spoiler alert: history says no.

The game itself was equal parts maddening and thrilling. Eleven men stranded, offense snoozing for eight innings, then suddenly, the ninth-inning panic button gets smashed. Anthony Volpe tied it up by racing home on a wild pitch — and Caballero finished the job after a nine-pitch war, dropping a single into center that scored Judge and cracked the tension. An incredible finish, yes — but why does it always take until the brink of death for this team to show a pulse?

So here we are. Clinched, but not satisfied. There are five games left, and the AL East is still dangling out there. Can the Yankees actually grab it? Absolutely. Do I trust Boone to lead the parade? Absolutely not. If he somehow fumbles this postseason with this roster, the solution is simple: cut this guy loose and find someone who can.

But for now — congrats to the Yankees, congrats to the fans who’ve suffered through the ride, and congrats to José Caballero, the unlikely hero. One dramatic walk-off down, but the real work? 

That starts now.