A Yankee fan turned Red Sox pitcher's take on MLB's most vicious rivalry ahead of Wild Card Series

Growing up in New Jersey in the 90s, it was pretty natural for a kid to be idolizing and modeling his own game from the late-90s Yankees, Derek Jeter most of all. The crazy part, and what is not natural, is years later making your Major League debut for the Red Sox against that same childhood team at Fenway.

I wrote about that night in more detail over at Business of Ball if you want the full story — the smell of the ballpark, David Ross coming out to the mound to jump my ass while telling me we were going to win that game, and striking out Jeter looking a few innings after he grounded out as my first big-league out ever. What I want to get into here is why this specific Wild Card matchup, two teams that've met in October seven times now, all since 1999, has me more excited than it has in years.

Growing up, this rivalry belonged to guys who'd already cemented their legacy inside it. Jeter at the center of the “Core Four” represented everything the Yankees stood for at the turn of the century. David Ortiz, Jon Lester and Dustin Pedroia, and that whole Red Sox generation eventually answered back with championships of their own. Every new chapter felt like it was extending something that already existed. This year (and for a little while now) feels different, because neither side has a player who's actually built upon their own signature postseason moment inside this specific rivalry yet (though Cam Schlittler's Game 3 last year could be the start of something great). Both rosters have their respective playoff experience, but neither has a legend.

Neither Yankees nor Red Sox have a postseason legend yet

Let’s look at Boston's side first. Roman Anthony is 21 years old, a $130 million extension already in hand, and about as talented as any player on either roster, but he doesn't have that signature moment attached to his name yet. Adley Rutschman was traded for these moments, and with the price tag Boston paid, he'd better perform. Payton Tolle takes the ball in Game 1 as a big, physical lefty with a loose, funny personality that makes him one of the most fun players in the game to watch, but he hasn't authored his own chapter in this rivalry either.

On the Yankees' side, Schlittler is the name I keep coming back to. He grew up in Massachusetts as a Red Sox fan, an almost perfect mirror of my own story in reverse, and now he's the Game 1 starter against the team he rooted for as a kid. He's got an edge to him on the mound that I like a lot, and pairing his personality against Tolle's more laid-back, physical presence is exactly the kind of contrast that makes days like this fun to watch as a fan of the rivalry itself, regardless of which side you're on. Max Fried takes the ball in Game 2 against Sonny Gray in a battle of two of the more polished starters in the sport and gets an opportunity to continue his Yankee legacy that has started in very promising fashion. Having Gerrit Cole as your Game 3 starter is ridiculous — Cole is one of the most decorated active pitchers, and one of the most fierce competitors — and I cannot wait to see him compete in this rivalry this October, knowing the window is closing.

And then there's Aaron Judge, whose availability is still a huge question mark. He's battled a rib injury most of the season, limiting him to 66 games, then a calf strain that kept his Wild Card status uncertain right up to game time (he's officially been ruled out about 10 hours before game time). As he readies to watch from the dugout and attempt to be ready if the Yankees survive their first challenge, his situation represents this whole series. Even the Yankees' best player, a two-time MVP and probably the best right-handed hitter ever, hasn't authored a signature Yankees-Red Sox October moment of his own yet either.

That's exactly why I can't stop thinking about this series. When I made my debut in 2014, I understood almost immediately that this rivalry isn't really about two fan bases disliking each other. It's about the responsibility that comes with putting on either uniform in games like these, whether the standings mean anything that year or not. David Ross taught me that on a random August night in a lost Red Sox season, and a couple months later I watched that same roster stop everything to honor Jeter's final game at Fenway — because respect for what came before still mattered even in defeat.

This series gives an entirely new group of players that same opportunity. Somebody on one of these rosters is going to get a hit, make a pitch, or do something that seems ordinary in the moment and ends up being exactly the kind of thing this rivalry remembers a decade from now. I have no idea who that ends up being and neither does anyone else watching the next few nights. That's what makes it worth tuning in for, whichever uniform you're rooting for.

Schlittler against Tolle in Game 1, Fried against Gray in Game 2, Cole and Suarez in Game 3. Ben Rice, Cody Bellinger, George Lombard Jr., and maybe even Anthony Volpe all seem primed for their signature Yankee moment. There is a legend still waiting to be written on either side. As a Yankees fan who ended up on the other side of this rivalry myself, I can't wait to see who steps into that role first.

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