Brian Cashman’s Fatal Flaw Might Hold Yankees Back

The 2019 MLB trade deadline has come and gone and from a Yankee fan perspective, it was rather quiet. Going into the trade deadline, the Yankees had one goal and one goal only; improve their suspect starting pitching rotation. Unfortunately for Yankees fans, general manager Brian Cashman and company failed to do just that.

They missed out on Toronto Blue Jays right-handed pitcher Marcus Stroman, who was traded to the New York Mets, as well as Cleveland Indians ace Trevor Bauer, who was traded to the Cincinnati Reds as part of a three team deal with the San Diego Padres. The only move the Yankees made was trading right-handed relief pitcher Joe Harvey to the Colorado Rockies for left-handed minor league pitcher Alredo Garcia.

To add insult to injury, the team they will possibly battle for the American League pennate, the Houston Astros, arguably made the biggest trade of the deadline, acquiring former AL Cy Young award winner Zack Greinke from the Arizona Diamondbacks. Meaning in order to make it to the Fall Classic, the Yankees will have to get past an Astros starting rotation featuring Justin Verlander, Gerrit Cole, and Zack Greinke.

This will be a very daunting task for the Yankees indeed, as their starting pitching has been a problem. Yankee starting pitching has pitched to a 4.77 ERA this season, 17th in all of Major League Baseball. Masahiro Tanaka has struggled to pitch a consistent splitter. J.A. Happ and CC Sabathia have shown their age. James Paxton, the Yankees big starter pitching acquisition this past offseason, has struggled majorly, pitching to a 4.72 ERA. Most of all, Yankees ace Luis Severino has yet to take the mound in the 2019 season. He has been on the 60 day IL dealing with a lat strain.

James Paxton 1st Inning MLB Ranks:

11.00 ERA – highest (min. 10 starts)
10 HR – 2nd most
22 Runs – 2nd most

— Katie Sharp (@ktsharp) July 26, 2019

For the Yankees to make it to and win the World Series, several things need to go their way. Severino needs to come back healthy and look like the Luis Severino of 2017 and the first half of 2018. At least two of their struggling starters need to figure it out as well. That’s a lot of things that need to go your way for you to realistically make a title run.

It’s time for us to ask the question of the day? How did the Yankees find themselves in this situation? How did their starting rotation become this big of an issue? As painful as this is to admit, we may have finally learned the weakness of Yankees general manager Brian Cashman. Cashman has without a doubt been a excellent general manager for the Yankees. Back in 2016, he rebuilt the team basically overnight. He solidified a new homegrown core of Aaron Judge, Gleyber Torres, Luis Severino, and Gary Sanchez. He’s found diamonds in the rough in Didi Gregorius, Aaron Hicks, Luke Voit, and Gio Urshela. He acquired a NL MVP in Giancarlo Stanton for pennies on the dollars. There’s no taking away from what Brian Cashman has meant from the New York Yankees.

Unfortunately, everyone has their strengths and their weaknesses. And based on his history, we can safely say that Brian Cashman has one big weakness as a baseball general manager. That is starting pitching and building a championship caliber rotation. While he’s excellent scouting position players, finding diamonds in the rough, and relief pitching, starting pitching has and continues to haunt the Yankees General Manager.

Brian Cashman explains why the #Yankees didn't make a big trade at the deadline.#YANKSonYES pic.twitter.com/tu3oLarm6v

— YES Network (@YESNetwork) July 31, 2019

When you look at Cashman’s recent accusations of starting pitchers, few of them have worked out. Back at the 2017 trade deadline, he traded for Oakland A’s right-hander Sonny Gray. Gray would go on to be one of the Yankees biggest busts as he couldn’t handle the pressure of pitching in New York. He would end up being traded this past offseason to the Cincinnati Reds. After acquiring J.A. Happ at the 2018 trade deadline, he re-signed with the Yankees in the offseason. Happ has regressed significantly from where he was down the stretch in 2018. Last but not least, Cashman acquired hard-throwing left-hander James Paxton from the Seattle Mariners. As we mentioned previously, Paxton has failed to live up to the hype as a New York Yankee.

Along with whiffing on the pitchers he’s acquired, he’s also missed out on trade acquisitions as well. Back in the 2017 offseason, the Yankees were heavily in the mix to land Pittsburgh Pirates righty Gerrit Cole. Ultimately, the Yankees didn’t want to part with both Clint Frazier and Miguel Andujar and Cole was traded to the Astros instead. Cole blossomed into an ace in Houston and is now one of the scariest threats in their rotation.

In the 2018 offseason, the Yankees were heavily targeting free agent Patrick Corbin, electric lefty from the Arizona Diamondbacks. However, when they found out that Corbin would receive a contract worth much more than the Yankees price tag of five years, $100 million, Cashman pulled out of the Corbin sweepstakes. Corbin then signed with the Washington Nationals and has picked up right where he left off in 2018. Signing J.A. Happ instead of Patrick Corbin could go down as one of Brian Cashman’s biggest mistakes.

However, that mistake doesn’t hold a candle to the mistake Cashman made back in 2017. The Yankees had an opportunity to acquire former AL Cy Young award winner Justin Verlander from the Detroit Tigers. Verlander was considered to have regressed from the dominant ace he used to be. Ultimately at the 2017 waiver trade deadline, Verlander was traded to the Houston Astros. Justin Verlander experienced on of the biggest turnarounds of any starting pitcher we’ve seen in recent memory, taking over the role as the ace of the Astros pitching staff. Verlander also haunted the Yankees in the 2017 ALCS, as he allowed just one run in his two starts in the series as the Astros went on to defeat the Yankees and go on to win the 2017 World Series over the Los Angeles Dodgers.

For the sake of argument, let’s play the “what if” game. Imagine if the Yankees had acquired Justin Verlander at the waver deadline instead of the Astros. In all likelihood, New York would’ve defeated the Astros in the ALCS and could’ve easily gone on the defeat the Dodgers in the World Series. Now imagine if the Yankees then gave Patrick Corbin the six year contract he got from the Nationals. The Yankees would have a rotation of Justin Verlander, Luis Severino, Patrick Corbin, Masahiro Tanaka, and CC Sabathia. That would’ve been a true championship caliber rotation.

Cashman said he understands that buyers have to overpay, but said he considered the prices were far too excessive. #Yankees

— Gary Phillips (@GaryHPhillips) July 31, 2019

Unfortunately, Brian Cashman missed out, which could be a big problem for the Yankees moving forward. We’ve all heard the phrase “pitching wins championships”, and there’s definitely truth to that phrase. It’s questionable at best whether or not the Yankees have good enough starting pitching to win the World Series. The reason for that is because Brian Cashman and the front office have been scared to overpay, whether in prospect, players, or money, to get the top end starters they need. Instead, they’ve acquired starters at their price that haven’t panned out, leaving the rotation in the state it is in currently.

Now we have to consider the worst case scenario, in that Cashman continues on this path, not willing to overpay for the starting pitching the team needs and instead settling on cheeper options. The Yankees rotation will continue to be a weakness, which will make it that much more difficult for them to win a World Series.

The scary part is when you consider the length of the Yankees championship window. Aaron Judge is 27 years old and in the middle of his prime. The same can be said for catcher Gary Sanchez, who is 26 years old. Giancarlo Stanton is 29 and will be 30 in November. New York’s roster is right in the middle of their prime. Meaning every year that Cashman fails to improve the Yankees starting pitching rotation is another year wasted of the prime of Judge, Stanton, Sanchez, and others. And the longer Cashman waits, the more the Yankees championship window will shorten.

Brian Cashman has always preached his philosophy of wanting to win championships, not just a championship. While that’s an admirable goal to have, the fact remains that you have to win one championship first before you start dreaming about multiple. Meaning that Cashman will eventually have to get out of his comfort zone and pay the price needed to get the Yankees the top end of the rotation starter(s) they need. Because if he doesn’t, the Yankees championship window just might close on him.