Before you ask, yes I wrote this while on vacation. I’m at the tail end of a 14 day trip to Europe, taking me from Spain to Italy. I’ve had almost no time to write from my cruise ship so thanks to Tyler and Mike for keep on the content coming. You may be saying “Nick, relax, take some time off,” but playoff baseball in the Bronx is once again ready to begin, with first pitch Wednesday night at the Stadium. But I had an hour van ride from the port of Civitavecchia to Rome and my family was asleep, so what else am I supposed to do?

Now playoff baseball is already intense, but it will be ratcheted up as the Yankees will face a familiar foe in the opening Wild Card round. Losing the division to the Blue Jays on the final day, though if we’re being honest it was lost early on the year with blown games galore, means a date with the rival Red Sox. A dream matchup for neutrals and even fans of both teams who revel in the matchups history.

That long and storied postseason history began in 1978 with Bucky Dents heroics in the winner take all game 163. The Yankees beating the Sox carried into the ALCS in 1999 and 2003, with dramatic moments seemingly following both series around. The Sox were talented underdogs until 2004, when it all changed. Since that fateful series that reversed the curse, the Yankees have failed to beat Boston in the postseason in 2018 and 2021, the most recent of which saw Gerrit Cole leave the Fenway Park mound embarrassed by Boston’s sluggers.

That word “embarrassed” has crept into the lexicon of this rivalry all too often on the Yankees side of things since 2004. The 2018 loss to Boston in the ALDS saw the Sox win both games in the Bronx, including a 16-1 beatdown in game three. Meanwhile the aforementioned single Wild Card game elimination was never close, while being marked by Yankee base-running blunders. Really when you think about it, it has gone beyond Boston, as the Yankees have been humiliated by every team that’s not an AL Central team in the playoffs since 09. And so I begin our preview by saying enough is enough, yes the Yankees won the pennant last year, but this road will challenge them much more, and it is time they answered the bell!

In the regular season, the Yankees struggled against Boston, going 4-9 with a lot of ugly losses in there. It’s funny looking back as on June 13th the Bombers arrived on Lansdowne street looking to bury Boston in the standings. That weekend the Sox swept them, traded Rafael Devers, and managed to improve the rest of the way. Their youthful mix of players, led by Roman Anthony and Ceddanne Rafaela, changed the vibe of their clubhouse…thankfully for the Yankees Anthony will miss this series with an injury.

The issues the Yankees have against Boston are the same ones they have against other good teams. They struggle to execute the basic fundamentals of the game and Boston takes full advantage of that. That manifested itself the most on the bases, where the Sox ran wild as they did all year, having stolen hags at a near 80% clip as a team. This is magnified by the Yankees defensive issues behind the plate, with Austin Wells and Ben Rice unable to control runners.

Ultimately this series will boil down to the Yankees playing sound baseball in all phases. While that may sound oversimplified, anyone who watches this team knows that doing the basics isn’t this team’s best trait and we all know what it cost them last year. All the additions the Yankees made this year though have gone a long way towards to improving this area of weakness. Cody Bellinger, Paul Goldschmidt, Ryan McMahon, Ahmed Rosario and Jose Caballero have all played a major part in this improvement. They have combined to correct the problems in the field, while also put the ball in play more, and run the bags better and more aggressively. Ya know…playing baseball.

Those improvements manifested themselves the last time the Yankees faced Boston, as they won two of three with all the players I mentioned above playing key roles in the set. It went deeper than that though improved pitching helped handle Boston as well, with the rejuvenated pen performed well. The most important members of the unit that still gives Yankee fans a heart attack are Luke Weaver, and David Bednar. Weaver despite some ups and downs this year performed well once again and will likely be leaned on to get multiple outs in games. Bednar meanwhile, has been fantastic since being acquired from the Pirates, taking the closers role from Devin Williams and nailing down the ninth. He has never pitched in a postseason game before though, and will have all eyes on him as he makes his October debut, especially as he must out pitch former Yankee and current Red Sox closer Aroldis Chapman, as well as set up man Garrett Whitlock who have been brilliant this year.

The rest of the pen outside of Tim Hill is bit like a game of Russian roulette. Devin Williams could have fastball command…or he could implode. Camilo Doval could embarrass hitters…or they could embarrass him. Fernando Cruz could strike people out…yeah no actually he’ll just strike people out. The point is Bednar, Weaver, and Hill will regularly feature along with some mix of the names I just mentioned and more. I would not surprised, especially in this series to see them backed up by a host of starters. Luis Gil and Will Warren are both candidates to be in the pen against Boston, which brings us to our next area of importance, the rotation.

The Yankees rotation was good all year long, a real testament to its members, as it could have been even more special. Imagine a world Max Fried and Carlos Rodon, who combined for 37 wins were joined by Gerrit Cole and a healthy Clarke Schmidt. But instead we lived in a world where they were backed up by Ryan Yarbrough, Will Warren, Luis Gil, and Cam Schlittler, all of whom performed admirably. Schlittler in fact did enough as a rookie to seemingly earn the start in a potential game three of this series.

But enough about them, let’s talk about the two aces. Max Fried was as advertised going 19-5 with a 2.86 ERA, and this is far from his first playoff rodeo…time to deliver Max. Meanwhile Rodon has come full circle in pinstripes, having earned the respect of Yankee fans going from good last year, to an 18-9 2025 with a 3.09 ERA. Rodon had an eventful yet solid postseason in 2024, but needs to be a bit more consistent this time around. The team’s postseason fate will rest on their left arms, and they’ll draw a tough assignment in round one not just against the Boston lineup, but against their opposite numbers. The Sox will send Yankee killer Brayan Bello to the bump in this series, but will more importantly match 18 game winner Garrett Crochet against Fried. Bello is 5-4 lifetime against New York, having pitched to a 2.35 ERA in those starts, while Crochet is 3-0 with a 2.90 ERA against the Bombers. This series could be very well pitched…something out of character for the rivalry.

Now to the bats…something this rivalry is known for. You could always define the history of this rivalry by its offensive stars. From Ruth, to Williams, to Mantle, to Yaz, to Reggie, to Rice, to Jeter, to Nomar, to A Rod, to Papi, to Judge to Betts…we could be here all day. These teams have always boasted loaded lineups, which has often led to their infamous four and a half hour 13-12 July games. But this series does not feature as many names like that, and in fact most of them are in pinstripes.

The Red Sox offensive stars are not to be discounted, particularly the aforementioned Rafaela and fellow outfielders Jarren Duran and Wilyer Abreu, and don’t forget about Trevor Story and Yankee killer Alex Bregman. With that said the Yankee lineup is deeper. Cody Bellinger has been a fabulous addition, a healthy Giancarlo Stanton has been dominant since his return, while Trent Grisham, Ben Rice, and a host of others have been great at the plate. Amongst that group of others is someone who in my opinion has to be great this postseason, that is second baseman Jazz Chisholm. Very few players have as much talent as Jazz, but the talent sometimes slips due to complacency. He had a strong year offensively when healthy and has been solid enough at second. Perhaps more importantly for this series, Jazz is hitting .271, with six homers and 19 RBI’s in 27 games against Boston in his career. If Jazz is a potential x-factor…then let’s talk about the guy who has to have a BIG postseason.

I love Aaron Judge, all Yankee fans do. He’s a superstar and a wonderful ambassador for the organization and the sport. But there is no denying that October baseball has become a black mark on his amazing resume. Despite having some big moments in his first two playoffs, in 2017 and 2018, the career numbers have fallen apart. While he had 16 homers and 34 RBI’s in 58 playoff games, he’s hitting just .205 and is still living down last year’s debacle in center field in the World Series. There have been too many strikeouts, too many AB’s that end with no productivity. The heart of the order is strong and deeper than years past, it may be good enough to carry him through a series, but number 99 needs to do the heavy lifting if he wants his first ring.

The last part of this preview brings us to the managers, perhaps the area with the biggest gap between two departments in this matchup. Aaron Boone in short, isn’t nearly as good a manager as Alex Cora. Cora is a master at pushing the Yankees buttons, starting runners, putting action on and making the Yankees play baseball…which as we said they don’t do well. Boone and his staff seem to be in the lab cooking a lineup to counter act Crochet’s quality, by sending out all righties in game one…a rumored lineup I’m very uneasy about. I don’t have a lot of faith in Boone as this team’s skipper, but like Judge this playoff run could determine his legacy.

Time to make a prediction, though I’m sure you could imagine where I’m going with this. I’ll take the Yankees, in three games over the Red Sox. I think this series will be hard fought, the games will keep people on the edge of their seats, but I think Yanks have just a little bit more to outlast Boston. This could turn into another classic moment in this rivalries history, so buckle up everyone. Now I just have to figure out how the hell I’m gonna watch it at 12 AM in Sorrento Italy. Until next time, “Andiamo Yankees,” (“Let’s Go Yankees” in Italian) all the way from Rome!

On twitter you can find Mike @Mike_Sheerin, Tyler @TMon_19 and Sean @SeanMartinNFL. Subscribe to the site by hitting the follow button in the bottom right corner and entering your email address. Check out our Instagram feed @thebroadwaybreakdownsports for special gameday and promotional content. Our podcasts are available on Spotify. Visit the Rangers Ed Shop by clicking the link on our homepage. Check out our mailbag page to join the conversation here on the site and on our partners show, The Rangers Ed Podcast! We’ll be back with more soon.