What is Wrong With the New York Yankees?

Before I get started, I want to be completely transparent here: for the last few years, I’ve begun typing season retrospectives much like this one, and each year, they end up not getting published and are left to rot here in my drafts bin. The reason for this is because as I go back to proofread these things, I don’t necessarily like the way I come off in these pieces. I’ve always hated the notion that Yankees fans are entitled crybabies who need to be humbled. But the truth of the matter is that the team’s last owner, George M. Steinbrenner, III, instilled in fans of his team that to the Yankees organization, any season that doesn’t end with a World Series Championship is a failure.

Let that sink in a minute…the team can have a 100+ win season, go 7 games in the World Series and lose the final game in the 9th inning on a bloop single, and that entire effort is considered a failure! That’s some high expectations, but considering everything the man put into his team year after year, I get it. It may not be right, but who doesn’t want that kind of commitment from ownership? George had been quoted as saying, “You show me a good loser, and I’ll show you a loser.” And, I have to admit…truth be told, in years where the team failed to accomplish the lofty objective, as a fan, I couldn’t wait to see George’s kneejerk reaction in the offseason! Those were often even more entertaining than anything that came before it! But one thing was always for certain….”The Boss” as he was often affectionately called, was dedicated to winning!

So here we are, it’s 2022, George is long gone since passing away back in 2010 just after his team last accomplished it’s singular objective in 2009, and his team hasn’t even been back to the World Series! Gone are the Derek Jeters, the Jorge Posadas, Andy Pettittes & Mariano Riveras. Even the last player tying the new generation of “Baby Bombers” to that “Core Four” group, Brett Gardner was not brought back this past year and remained a free agent all season, effectively being “retired”.

In George’s place now is his youngest son, Hal Steinbrenner, and still slotted in as the General Manager is Brian Cashman. Now Cashman gets a lot of praise throughout Major League Baseball circles as he’s kept the Yankees competitive for decades now, by constantly fielding playoff teams. However, due to the edict set forth decades ago by George, simply being a playoff team just isn’t good enough if you’re a New York Yankee. I understand that Hal would prefer the payroll stay under MLB’s luxury tax cap, but now you’ve got other teams in the league that are outspending the Yankees and for the most part, they’re reaping the benefits. Not to mention direct competition from the Mets & their new billionaire owner, Steve Cohen, should be lighting a fire under the Yankees’ asses to not be outdone by their crosstown little brother. So now we have Brian Cashman making trades and doing his best to sign the best players, but sometimes now, the Yankees don’t always get the top available players anymore. We don’t always win the bidding wars for players as the Dodgers, Mets, Red Sox, Phillies, Giants & Padres have now come to battle for the big names. Hell…even the Texas Rangers & Astros have emerged as teams willing to pay big for top players. So now, Brian Cashman is often settling for players he maybe wasn’t initially in on due to Hal’s refusal to push the payroll. So instead of Carlos Correa, Trevor Story or Corey Seager, the Yankees dealt catcher Gary Sanchez & 3rd baseman Gio Urchella to Minnesota for shortstop Isaiah Kiner-Falefa, catcher Ben Rortvedt & 3rd baseman Josh Donaldson. Rortvedt, I don’t think ever played a game for the Yankees all season long, IKF, while I like his propensity for getting on base as a contact hitter, his stats don’t compare to those shortstops I listed first, and Josh Donaldson was certainly a downgrade from Gio Urchella, while his contract (which he earned during his MVP year in 2015) says otherwise. Instead, now the Yankees are stuck paying him $25M per year — money that could better be spent elsewhere.

It’s plain and simple, Hal Steinbrenner needs to loosen up his grasp on the Yankees’ checkbook and Brian Cashman needs to go. Cashman can be linked to numerous bad deals for the Yankees. Here’s just a few of the bad moves he’s made over the years: Carl Pavano, Kevin Brown, Jacoby Ellsbury, Kei Igawa, Jaret Wright, Kevin Youkilis, Jose Contreras, Joey Gallo & Aaron Hicks…just to name a few. Now that’s not to say that Brian Cashman hasn’t been linked to a number of good Yankees acquisitions like CC Sabathia, Mark Texiera, Orlando Hernandez & Hideki Matsui, but his time as GM for the Yankees, in my opinion should be coming to an end — however unlikely that may be.

The last few seasons have been such a mixed bag of emotions. From long winning streaks to long losing streaks that make you think you’re watching the baseball version of Dr. Jeckyll & Mr. Hyde, to Corey Kluber throwing a no-hitter last season against the Texas Rangers, only to have his season ended when he went on the IL after his next start. Then there was the exciting news that the Yankees had won the Gerrit Cole free agent bidding frenzy, only for his aura to come crashing down when MLB cracked down on pitchers using SpiderTac and other substances to give them unfair advantages. Following that investigation was his disappointing lack of answers he had for the media at his press conference. It’s really just been one thing after another with this team for a good 20 years now. Anyone remember Jason Giambi’s half-assed apology following admission to using steroids in front of a federal grand jury? His apology was about as apathetic as you could possibly get…especially since he never actually stated what he was sorry for! And while we’re on the subject of steroids, I don’t know how Alex Rodriguez doesn’t get a mention here, with his 211-game suspension, which kept him out of an ENTIRE season!

Is it really too much to ask for players to not be trying to cheat their way to victory? Or maybe just a bit of morality be shown by some of these supposed superstars of the game who should be acting as role models that kids look up to. At least in the case of Aaron Judge, it appears that his 62-home run season appears to be a legit record set by a player who wasn’t on any sort of performance enhancing drugs! But he’s the next here on my list for this offseason. Last offseason, he accepted a one-year deal with the Yankees in arbitration, granting him $19M and bet on himself. Now it can be said that he won that bet by a long shot, but I can’t help but think of how many of those games he played in, had he had a long-term contract, if he had a little soreness in his elbow or shoulder, would he have taken himself out of the lineup as he had in previous years? Also, batting leadoff for a good majority of the games this season granted him more at-bats than he would have had, had he batted in his typical third or fourth spot. So don’t get me wrong, it’s an impressive feat of hitting mastery, but you need to also consider everything he did have going for him. But here’s the kicker though…just as in previous years, as September turned to October & the MLB Postseason was upon us, and Aaron Judge started seeing only the best pitchers on the best teams, his bat once again, went silent. Now for most baseball fans, 62 home runs in a season, the possibility of winning the Triple Crown, the League MVP…those are all awesome achievements, but he’s playing for the New York Yankees, and every Yankees fan knows that it’s not what you do during the regular season that makes you a legend in New York, it’s the postseason heroics. It’s Derek Jeter, the shortstop being the cutoff man on a throw from right field to home plate, being on the foul side of the first baseline and getting Jeremy Giambi out at home that get you into Monument Park. It’s coming off the bench in extra innings and hitting a walk-off home run against Boston in the 11th inning of the 7th game of the ALCS, or hitting a 3-run homer off Mark Wohlers to tie Game 4 of the World Series on the road in Atlanta. I’m not saying he’s the reason the Yankees haven’t been to the World Series since 2009, but he’s certainly not been the guy who’s getting them there. Also, with all the talk about a possible new contract with the Yankees, the possibility of him being named the next team captain (the first since Derek Jeter retired following the 2014 season) he needs to be that guy who pushes the team by example to step up to get back to the World Series, and I just haven’t seen that from him yet.

Would I like him to come back to the Yankees next year, absolutely. For the entire march to his 62nd home run, he kept saying the right stuff: that he’s more concerned about winning games, that it’s a team sport and he just wants to do his best to push the team forward. But if he’s unable to continue to do that when the weather turns cold in October, then all the lip service in the world isn’t going to offset his lack of production when it matters the most.

Another area of weakness for the Yankees would appear to be their analytics department, or rather their execution of said information. Michael Kay hit this topic right on the head during the postgame show on the YES Network following the Yankees’ Game 3 loss to the Astros. In the 6th inning, with the team already down two games to none, with bases loaded and Gerrit Cole on the mound, already losing the game 2-0, with the back end of the lineup coming up, Boone’s information told him that in that spot, Lou Trivino was his guy to go to instead of his best bullpen arm who is far more used to pitching in high-pressure situations, Jonathan Loaisiga. And while I’d like to think that given his time as a player and even his tenure as Manager of the New York Yankees, that his gut would have told him this as well, but instead, he relied on his graphs and spreadsheets, which earned him yet another loss at the hands of the Houston Astros. Unfortunately, I know that Aaron Boone is just doing the job that Brian Cashman wants him to do. He’s the yes-man Cashman wants as a manager for the team instead of a Buck Showalter type who can take all the information given to him and make his own educated decision on his own using both the analytics and his own intuition from his past experiences. So once again, Brian Cashman’s system does not work and he needs to go. At the very least, the people he’s hired to interpret the spreadsheets and graphs need to get better at it along with Cashman/Boone’s decision making in the heat of the moment.

I’m sure that by now, you’ve gathered that I’m not happy with a number of aspects with this team. In my perfect world, Brian Cashman is gone along with Aaron Boone. To replace Cashman, I’d make a serious push for Billy Beane from Oakland. I know he’s not their General Manager anymore, but what he managed to do with the tight budget he had out there, I’d love to see what sort of team he would field in New York with the payroll he’d be able to work with here. He’d be like a kid in a candy shop. As far as Aaron Boone is concerned, I think he generally handles the media here in New York pretty well, considering the pressure cooker he operates in, so I’d consider keeping him while also keeping a watchful eye on other options coming available around the league because, as I said…his decision making in high-pressure situations sometimes leaves a bit to be desired.

As far as players are concerned, at the top of my list to unload this offseason is Josh Donaldson. He makes far too much and produces far too little offensively. Defensively, he’s good, but I think that can be found in a more affordable alternative. I’d also like to see Aaron Hicks in another uniform next season as well. As for free agents, Aroldis Chapman is not welcome back. I’ve seen more than enough shaky innings from him over the last couple years. He’s lost his edge and needs to go stink it up somewhere else. I’d like to see Anthony Rizzo back, he’s been a a good fit at first base for us and was one of the few players who didn’t constantly strike out in the ALCS. Sadly, he and Harrison Bader were really the only two threatening hitters in that series for the Yankees. I’d also like to see Jameson Taillon back, he was a fairly reliable starter all year for us & when the ALDS games got postponed due to bad weather in New York, he stepped in to start Game 1 of the ALCS and did an admirable job. As a fan, I felt far more confident with him on the mound than I did having Frankie Montas on the mound in relief that same game. Also, while I’m on the topic of Frankie Montas…he’s a guy I’d like to see in another uniform next season as well. Cashman made a trade for him at the trade deadline to be another starter in the playoffs, but just as a number of other players have found in the past, he’s just not cut out to play in New York. Pitching in Oakland for the Athletics is an entirely different thing than pitching for the Yankees in New York. Nothing against him, but he’s just another in a long line of pitchers like Sonny Gray, Jeff Weaver & Félix Heredia who just can’t do it here. I’d also like to see them make a play for Andrew Benintendi since we didn’t get to see a whole lot out of him before he went down injured after trading for him.

So that’s my initial feelings about this offseason for the Yankees, I’m sure I’ll have some comments & thoughts on the next moves the team does, at which time, I’ll be right back here to share.

Thanks for reading!