Brian Cashman, A Tale of Perpetual Mediocrity

"Mediocrity? The Yankees haven't had a losing season since 1992." Yeah, the Yankees haven't had a losing season since the year I was born. When looking at other teams around the league, it actually seems miraculous, doesn't it? Year after year, the A's are mired in defeat (It was pointed out that they're 1056-1073 since 2010, so not terrible). The Angels continue to spend money and acquire talent, yet make all of the wrong decisions. The Diamondbacks are perpetually rebuilding. The Royals trusted the process and had one dominant year to compensate for many, many bad ones. The Yankees 30 season winning streak is something fans of other teams envy and despise. In fact, no team is particularly close, with the Cardinals currently boasting a 15 season winning streak that began in 2008. Unfortunately for them, this will be coming to an end in 2023. So what exactly makes the Yankees mediocre during Cashman's tenure? First, let's look at the beginning of Cashman's role as GM. The hyper-intelligent, blue-eyed Cashman began his career with the New York Yankees in 1986, serving as an intern whilst a student at Catholic University in DC. During his internship, he learned the administrative skills that would later be used to secure the job as Yankees GM. Upon graduating university, the Yankees hired him as a full-time baseball operations assistant. This position came with a wide range of duties, from scouting to contract negotiations. Quickly working his way up the ladder, he was promoted to assistant farm director in 1989. Clearly, the Yankees believed Cashman's approach to scouting young talent was a valuable asset. In 1991, he was promoted to Director of Minor League operations - an expansion of all of his previous duties. He was now the guy running the entire pipeline of young talent for the most storied franchise in the history of baseball. In 1993, he was promoted to assistant GM to Gene Michael. Basically an internship for becoming GM of the Yankees. We'll get back to Gene Michael in a minute. In 1996, Bob Watson replaced Gene Michael as GM of the Yankees, with Cashman retaining his role as assistant GM. Two years later in 1998, Cashman becomes GM of the New York Yankees. He's retained that role since.

Since becoming the GM in 1998, Cashman has overseen 4 World Series titles. 1998, 1999, 2000, and 2009. One would think four Championships makes Cashman one of the all-time great GMs. But let's now take a look at the players Gene Michael drafted or acquired:

• Derek Jeter, 1992, 71.3 bWAR

• Mariano Rivera, 1990, 56.3 bWAR

• Bernie Williams, 1985, 49.6 bWAR

• Jorge Posada, 1990, 42.6 bWAR

• Paul O'Neill, 1993 from CIN, 38.8 bWAR

• David Cone, 1995 from TOR, 62.3 bWAR

• Tino Martinez, 1996 from SEA, 29,0 bWAR
  

When you think of the Yankees dynasty, these are the guys you think of. And none of them were drafted or obtained by a young Brian Cashman, but rather Gene Michael. Unfortunately for Michael, the Yankees had missed the playoffs in 1994 and 1995 during his tenure as GM, and George Steinbrenner just didn't have the patience to deal with him any longer. He was an owner interested in immediate results - and can you blame him? He was throwing down ridiculous amounts of money to compete every year. Many fans wish Hal, often times perceived as stingy with his cash, inherited this trait from his late father. But in this case, George's impatience led to the firing of a GM who found, frankly, a ridiculous amount of talent through the draft, trades, and free agency. It's hard to argue there's a GM that's done a better job since, or ever. There were also rumors George was envious of the praise Michael received for drafting Posada, Rivera, and Jeter. George was just a personality larger than life, with the money and ego to back it up. So under Brian Cashman, the Yankees have won four titles, three being with rosters Gene Michael created. This didn't really matter though. George was happy to let Cashman get the perceived credit. Cashman had a tireless work ethic, was one of the first managers to embrace analytics, was young and well-spoken. and played to George's ego. He was calm, collected, and always communicated in a way that didn't encroach on George's reign. This is something Gene Michael unfortunately could not do. Let's look at Cashman's key contributions to the 2009 roster:

• Mark Texeira

• Alex Rodriguez

• Robinson Cano

• CC Sabathia

• Brett Gardner

• AJ Burnett

Cashman did a good job acquiring Texeira, A-Rod, and CC. A-Rod and CC in particular had long, successful careers in New York, with CC being particularly beloved by fans and involved in Yankees operations to this day. Mark Texeira was never able to replicate the success he found in LA, but offered a decent bat and Gold Glove defense. AJ Burnett was mediocre and unpredictable. Brett Gardner had an extremely underrated career, manning CF for a decade and compiling 44 bWAR. Robinson Cano was by far the best player Cashman drafted, but he came with his own host of problems and eventually left for Seattle because Cashman simply couldn't get the job done. Cashman did enough to win a championship, but clearly not enough to build a dynasty. At this point, he had a World Series loss to the Marlins under his belt and desperately needed this win. But remember, Gene Michael's guys still played a major role in the 2009 championship. Jeter, Posada, Rivera, and Pettite were still extremely talented players at the back-end of their careers - a testament to Gene Michael, and a gift to Cashman.

Now make no mistake, Brian Cashman was a good choice and still won a championship. His focus on combining analytics and modern stats with scouting was ahead of its time. His combination of old-school scouting and a focus on the numbers did help him build fairly well-balanced teams, and he was one of the first GMs to form an official analytics department. With this being essential in modern baseball, it's no wonder he's lasted as long as he has. He was ahead of his time. But being ahead of his time doesn't make him the best at what he does, and that's the problem. Cashman has simply been surpassed at his own game. Nobody is going to argue Cashman is better than Erik Neander or Mike Hazen. It's not like Cashman's Yankees are bad. The mid 2010s have been fairly successful for the Yankees, if you consider ALCS appearances and regular season records a success. The Yankees reached the ALCS in 2017, 2019 and 2022. That's one series away from the World Series. Many clubs would consider this a success, but for a club with such high expectations, a storied history, and a seemingly limitless budget, it could only be considered mediocrity. So why exactly couldn't the Baby Bombers take that final step? Well, two reasons. The first reason was a reliance on stop-gaps. A 2017 lineup that features Greg Bird, Starlin Castro, and Chase Headley is simply not going to accomplish anything. And beyond that, Jacoby Ellsbury's horrible contract sunk any possibility of replacing these guys in free agency. In all honesty, Cashman was lucky he even got the production he did from Didi Gregorious, who quickly fell off in 2019 and is now out of the league. Aaron Judge, much as he does today, covered too many of the lineups flaws. So what did Cashman do to fix this? He traded for Giancarlo Stanton, which, at this point, may be the worst contract in all of baseball. In 2023, Stanton has regressed significantly, hitting .202 with a .723 OPS. And since 2018, Stanton has appeared in only 238 games for the Yankees. He appeared in 158 for the Marlins in 2018. Stanton has been unreliable, consistent, and most importantly, eating away at the Yankees salary. Worst yet, he's under contract until 2028. Disastrous. Especially when you consider this prevented them from signing Bryce Harper or Manny Machado.

The Second reason? The existence of the Houston Astros and GM Jeff Lunhow. Lunhow was simply a better a GM than Brian Cashman, building a roster that has stonewalled the Yankees in all three ALCS series since 2017. We can speculate whether the Yankees would have defeated the Astros had they not cheated, and then would have proceed to defeat the Dodgers in the World Series. It's a fair question. But the reality is, Lunhow was a better GM than Brian Cashman, and that's all there is to it. Lunhow built a talented, complete roster working with significantly less money - meaning less room for mistakes and more pressure to hit on draft picks. And somehow, he vastly outperformed Cashman with far fewer resources.

Now here we are in 2023, and the Yankees are on the verge of their first losing season since 1991. Let's examine why this current roster is failing.

1. The Giancarlo Stanton contract, as previously mentioned, is destroying this team. Beyond financial flexibility being destroyed, building a lineup around Stanton is nothing short of a riddle. His legs are completely shot making him a liability in the OF, and being relegated to DH is hurting the Yankees lineup. He's simply not producing in a spot where it's easiest to find a guy that can produce. The DH spot should make building a lineup easier, not more difficult. He's a .200 hitting ground-ball machine that can barely run the bases.
   

2. Trading Gio Urshela and Gary Sanchez for Josh Donaldson and and Kiner-Filefa was a mistake. Gary Sanchez, once thought to be on pace to be one of the greatest power-hitting Catchers of all time, found himself slumping at the plate and struggling as a backstop. The Yankees decided to move on. At first, it appeared to be a good decision, as he didn't look good for the Twins at any point. But fast forward to 2023 and Gary Sanchez has 2.3 bWAR to go 17 HRs in only 215 ABs. That's more production than Higashioka, Trevino, and Rortvedt combined. The Catcher position has been a blackhole in the Yankees lineup and a main culprit for why the offense is so miserable. Not only is Gary Sanchez swinging a hot bat, but he currently owns a 61st percentile Framing ranking according to Statcast. He has 9 defensive runs saved, according to Frangraphs. That's right, Gary Sanchez is no longer a defensive liability, and is once again a slugger. Then there's Urshela, who was traded for and replaced by Josh Donaldson. Just beginning with intangibles, Gio Urshela was a beloved underdog among the fanbase who smiled often and backed up the charm with smooth play. His 2019 breakout was a huge part of the Yankees success. He was also extremely cheap, earning less than $9 million per year. So when Cashman traded the well-liked Urshela for the hated, controversial, aging Josh Donaldson, fans were left scratching their heads. Cashman claimed the Statcast numbers indicated Donaldson was primed for a bounce-back year, but this never came to fruition. It's understandable to believe in the analytics, but unfortunately Cashman hasn't learned this doesn't apply to aging players approaching 40. Donaldson's defense has been gold glove caliber at the corner and has allowed him to compile positive WAR, somehow, yet none of us can be convinced that Donaldson at $21 million possesses more value than Urshela, who is hitting .300 for the Angels this season. He may lack power and a high OBP, but a player hitting .30o can at least drive in runs. Something the Yankees desperately need.
   

3. On July 29th, 2021, the Yankees traded Ezeqial Duran, Trevor Hauer, Glenn Otto, and Josh Smith to Texas for Joey Gallo. This trade has turned out to be a complete disaster. Joey Gallo was nothing short of terrible for the Yankees in his brief stint in NY, and Ezeqial Duran has been noting short of incredible in his rookie campaign for the playoff-contending Rangers.

Duran has been nothing short of productive during his rookie campaign, slashing .287 with an .806 OPS. His defense has fallen off later into the season, but with a 99th percentile arm strength and 91st percentile sprint speed, he clearly possesses the athleticism to excel in the infield. He's on his way to becoming a complete player with tremendous upside. And even at the current moment, he'd be the second best hitter on the Yankees behind Judge. Maybe even more importantly, having Duran would have given the Yankees the ability to trade Peraza or Volpe to bolster the lineup at the trade deadline, a lineup that would have already been much more competitive due to Duran's presence. This deal already looks terrible for the Yankees, but if even one of the other prospects involved in the deal becomes a decent MLB player, it looks like a disaster.

4. On August 1st, 2022, the Yankees traded JP. Sears, Ken Waldichuk, Luis Medina, and Cooper Bowman for Frankie Montas and Lou Trivino. This deal became an unmitigated disaster when Montas proceeded to compile a 6.35 ERA and 1-3 record with the Yankees. Then it was learned he had an injury before he was traded, and has essentially been non-existent for the club since he was shut down. He has not pitched in 2023. Lou Trivino was fairly decent out of the pen in 2022, but he wasn't the centerpiece of the trade. They were counting on Montas to be a genuinely good starter. Luis Medina has been extremely inconsistent for the A's, but has shown flashes of good stuff. He had a stretch of dominant starts from June 20th to the end of July. Here's an article from frangraphs detailing his brief period of dominance. https://blogs.fangraphs.com/luis-medina-is-dealing/ JP Sears may or may not become a complete pitcher, but his 1.6 WAR and 1.23 WHIP indicates he's serviceable at the moment. Maybe the worst part of this trade, though, was counting on Montas to become a rotational piece left the team's pitching extremely vulnerable. Rodon playing poorly, German entering rehab, and Nestor being injured and unable to go deep into games has only compounded this failed acquisition. Which brings me to my final trade. 5. Jordan Montgomery for Harrison Bader. This one may be a little controversial because Bader is well-liked, personable, and unquestionably smooth in the field. But make no mistake, the Yankees need Jordan Montgomery much more than they need Harrison Bader. Jordan Montgomery has compiled 3.1 bWAR this year to go with a 3.12 ERA this season, which would make him the Yankees second best pitcher. Harrison Bader currently has 1.1 bWAR on the campaign and has missed a substantial amount of games, which should have been predictable considering he was often injured in St. Louis and actually came over injured. Now, with Everson Pereira called up, Jason Dominguez knocking on the door, Harrison Bader entering free agency, and the Yankees desperate for a starting pitcher....yeah, this trade was a loss.

I'd also be remiss to not mention the Sonny Gray trade, only because Sonny Gray has been excellent since leaving the Yankees, which naturally has fans questioning Cashman and the Yankee's organizational approach towards pitchers. This may have been remedied with he acquisition of Matt Blake, who has been impressive, but it doesn't change the fact that Sonny Gray and even Lance Lynn failed in a Yankees uniform under Cashman's watch. Even now, Sonny Gray has racked up an incredible 4.3 fWAR in 2023, which is good for 19th in all of baseball. How the Yankees were unable to allow an aged 27 Gray to excel is a question worth asking. Simply put, Cashman has been mediocre as Yankees GM when you consider the resources he has at his disposal and the talent he inherited when he first accepted the position in 1998. When you consider the Yankees failures over the past decade and what another GM may have been able to do with the Yankees resources, it's easy to come to the conclusion Cashman should have run out of good will by this point. It's understandable that Hal may have become complacent, accepting winning season after winning season and a steady stream of revenue. Being a playoff contender every year has to be comfortable, and the unknown is always uncomfortable. Hal grew up alongside Cashman, and he's basically all he knows. Cashman is a remnant of his father's legacy. Maybe to Hal, Brian Cashman is like a warm, worn-out blanket that used to keep him comfortable hen he was a child, and just can't let go. It's time to let go.