Boston Red Sox – Threeunassisted

I Would Rather Lose to the Red Sox Than the Astros in the Playoffs

As a fan of the New York Yankees, I have always been told to hate the Boston Red Sox. Although it is virtually impossible for me to tuly hate anything, I still have a strong dislike for the Sox. That being said, to show you how little I can hate, I was actually not livid with the events of the 2004 playoffs. I had an uncle who was a lifelong Boston fan pass away shortly after the 2004 World Series ended. I was happy to know that he could leave this Earth and have seen a championship by his beloved Red Sox. After that is a different story. Boston would go on to capture World Series titles in 2007, 2013 and 2018. That is more prolific than the Yankees’ single championship in 2009 during this stretch. Let’s also not forget playoff defeats absorbed by the Yanks at the hands of the Sox in 2018 and 2021. In short, there is not much to like about our New England neighbors.

I can’t stand the Astros in the playoffs. Credit: UPI

So why do I have that wacky headline?

Let’s start by rewinding one year to last season’s Wild Card round. The Yanks beat the Red Sox in three games, snapping a three series playoff losing streak. That’s one reason. Another is that I have over 40 years of watching this rivalry with much of my formative years witnessing the Yankees coming out on top. A loss to Boston in 2026 would not nearly be stinging as it was in 2018. By my count, I still have 1978, 1999 and 2003 playoff victories to visualize, plus a bunch of World Series titles in my back pocket.

A loss to the Astros? Unacceptable.

The next time the Yankees beat the Astros in a playoff series would be their first time. The Astros have been to three World Series over the last nine years. On each occasion Houston found themselves in the Fall Classic, they ended up beating the Yankees in the ALCS. The Astros of 2026 remind no one of those teams. Yet, here they are leading the American League West after being nine games under .500 at the end of May. Jose Altuve is my age. No one named Justin Verlander and Framber Valdez are throwing strikes. George Springer is not around to swat a big home run. You have Yordan Alvarez mashing all pitchers and Josh Hader throwing darts to close out games. That’s it. How can the Yankees, even without Aaron Judge, lose another ALCS, or even a divisional round to this group?

If last week is any indication, the threat is very real. Houston won two out of three games at Yankee Stadium.

It is time for the New York Yankees to bury the Houston Astros once and for all. Erase all of the postseason demons that we can’t seem to shake. Beat this organization for the first time in five playoff tries. I feel my blood pressure rising at the very thought of having another season ended by those orange uniforms. Losing to the Red Sox is problematic. Losing to the Astros is catastrophic.

The Yankees Better Win This Series

The headline is quite obvious. Yes, the New York Yankees need to win their Wild Card series against the Boston Red Sox or else they cease playing baseball for the rest of 2025. They not only better win this series in order to continue on a quest for a championship, but they also need to do so because of the potential implications of defeat. For if the Red Sox beat the Yankees, I believe the reverberations will be felt all the way up to the front office. I like to call it an organizational earthquake.

Does Aaron Boone survive another Red Sox playoff defeat? Credt: New York Post

A loss to the Red Sox in this round in this year would be the one scenario where the jobs of Aaron Boone and Brian Cashman would be in jeopardy. To be clear, I am not calling for the dismissal for either man. Plenty of other people will do that for me. However, look at the records of both organizations over the last 20 years, beginning in 2005. Boston has won three World Series under three different managers and three different front offices. The Yankees have won the World Series just once during that time. Cashman has been the team’s chief decision maker during these last two decades. More recently, let’s compare the managers. Boone and Alex Cora each assumed the helm prior to the 2018 season. Cora’s Red Sox beat Boone’s Yankees in the divisional round on their way to winning it all. The two teams also squared off in the 2021 Wild Card game with Boston once again coming out on top. The Red Sox have been flat out better. Why do I believe a loss this year could be almost, if not more catastrophic than the 2004 meltdown?

Not only have the Sox won more recently, but they have also fallen down and gotten back up. Yes, the Yankees have been a model of consistency, with playoff appearance after playoff appearance. Cora was suspended for the 2020 season. Boston has finished last three times since 2018. The front office changed again. The Red Sox were roasted for trading Rafael Devers in May. Yet, here the Red Sox are, threatening to derail another Yankees’ postseason run. It’s bad enough they owned the Yankees during the regular season. Can you imagine Alex Cora and company once again celebrating a playoff series victory on Yankee Stadium soil? How does Yankee ownership not make wholesale changes should they lose this first round? Their arch nemesis, the one that has owned them over the last 20 years, the one that has risen, fallen and then risen again all the while the Yankees go another year without a championship is pretty humiliating.

There has to be repercussions for this specific failure. I’m afraid Boone might be the one who pays the price. If not, expect a cataclysmic meltdown from both fans and the media. If you thought last year’s World Series defeat triggered this group of people, you haven’t seen anything yet.

Can the Yankees Finally Top the Red Sox?

Wonderful. Well not really. Tonight’s New York Yankees-Boston Red Sox game is on Apple TV. Therefore, with the Yanks winning 2-0 as I write this, I have the displeasure of not viewing it. Instead, I get the non-privilege of watching the New York Mets continue their second half from hell. Yanks-Red Sox in September equals national TV broadcasts: tonight, Apple TV, tomorrow, MLB Network and Sunday, ESPN. The two teams have a storied rivalry, hence the national audiences. However, the 2025 season is anything but a rivalry as the Sox have dominated the Yanks, winning eight games out of ten.

Time for Max Fried to be the big money pitcher the Yankees pay him to be. Credit: NY Post

New York is due.

New York is primed to sweep Boston.

Boy I hope so.

I say that are ready for this because Aaron Judge is peaking at the right time. He has spent most of this last week chasing down and surpassing Yankee legends Yogi Berra and Joe DiMaggio on the career home run list. Hopefully, this momentum carries over into the playoffs and buries the narrative that he can’t perform when it counts. Look at Giancarlo Stanton. The last time his batting average was better than his current .268 this late in the season was four years ago. He has 20 home runs in 63 games. I get this feeling Max Fried will have a dominant start on Saturday like another legendary Yankee , Whitey Ford. His big Yankee moment has to come at Fenway Park. Most of all, this team is too talented to remain Boston’s punching bag for yet another three games. They need to showcase why they are the defending American League champions.

In all likelihood, these two teams will meet in the first round of the playoffs. This series, with the teams separated by a half game, will go a long way in determining who will be the host. A Yankees sweep would stop the Red Sox aura of invincibility surrounding these meetings in 2025. A Yankee series defeat will leave a ton of questions about how equipped this team is to return to the World Series.