AL East

It’s Time For The Yankees To Part With Brian Cashman

Experts and non-experts alike have had much to say about both the Rays and the Red Sox recently. Most of the talk centers on whether or not the respective approaches of each organization are the best way to succeed, and if they can succeed, to what extent.

For those of you who may only be paying attention tangentially, here’s a quick synopsis from a slightly different perspective:

For the second year in a row, Tampa Bay had both a better regular-season record than the Yankees and went further in the postseason as well. They managed to do that while trading away their best pitcher and their second-best position player (both according to bWAR) during the two-season stretch. As you likely know, they also did it using a payroll that was 26 percent of the Yankees’ payroll in 2020, and 30 percent in 2021.

By the time the 2021 season began, the Red Sox had parted ways with eight of the top 12 WAR producers from their 2018 championship team, including the franchise’s best player since Mike Yastrzemski’s grandfather was playing. Additionally, their best pitcher was only available to them for 42 innings this season. Yet, the fire sale version of the Red Sox won as many regular-season games as the Yankees in 2021 and has advanced further in the postseason too.

It’s not a stretch at all to say that the Yankees have the third-best front office within their own division – heck, looking at Toronto’s current roster, the Yankees might have the fourth best. This is a culmination of close to two and a half decades of Brian Cashman being a good GM, but not good enough – and as long as he’s sitting in the GM’s chair in the Bronx, the Yankees will be perpetually stuck playing the role of one of the bridesmaids.

Let’s review how we got to this point:

Cashman became the Yankees GM on February 2nd, 1998. He inherited a roster built by Gene Michael and Bob Watson that had won a World Series in 1996 and then improved in 1997, winning more regular-season games in a tougher division. The roster Cashman inherited was made up of good young players who were becoming great young players and veterans who had plenty of gas left in the tank. That roster made up the overwhelming majority of contributors to what would become the 1998, 1999, and 2000 champions.

The only acquisitions of Cashman’s to those teams were Chuck Knoblauch, Orlando Hernandez, Roger Clemens, and David Justice. Clemens was the best pitcher in baseball whose salary Toronto no longer wanted to pay, and everybody knew El Duque was good, so it wasn’t so much sound baseball decisions that led to the acquisitions of those two as it was the team owner’s checkbook.

Knoblauch was acquired within a few minutes of Cashman being hired. George Steinbrenner had ordered Bob Watson to trade Bernie Williams and Andy Pettitte for Knoblauch or be fired. (Watson felt quitting and laughing, in whichever order, was a better option for all involved – read Jon Pessah’s “The Game” for the full story.) After Steinbrenner calmed down, he approved a deal that sent Eric Milton to Minnesota for Knoblauch for his new GM.

Justice was acquired in July of 2000, and was a big part of the 2000 champions, both in the regular season’s second half and in the postseason. He did come at a hefty price, however, as Jake Westbrook went to Cleveland as part of the return for Justice.

All told, those four acquisitions contributed approximately 5 percent of the WAR for the championship teams of 1998, 1999, and 2000 (yes, I did the math). That is to say, Cashman’s role in those teams’ success was quite minimal. However, the impact of some of his moves would have long term consequences: Eric Milton went on to be one of the best pitchers in the American League over a three-season stretch and Jake Westbrook went on to become an All-Star and one of the AL’s best pitchers for a four-season stretch.

Remember, from 2003 to 2007 the Yankees had a powerhouse lineup with some of the best offensive teams in MLB history that gave them a legitimate chance to win every season.  They did not, in part because the pitching staff assembled by Cashman to push them over the top consisted of the acquisitions of Javier Vasquez, Kevin Brown, Jose Contreras, Jaret Wright, Kei Igawa, and Jeff Weaver.

Don’t misunderstand: I’m not saying that we wouldn’t all do the Justice trade again given the opportunity. I’m saying that in totality, Cashman’s moves had a very small imprint on the dynasty compared to the impact of his predecessors and that Eric Milton and Jake Westbrook sure would have been nice to have on those offensive heavy, light on pitching teams that soon followed. Ted Lilly would have been nice to have as well, but he was sent to Oakland in the three-team deal that had Detroit send Weaver east. (Weaver produced 1.2 WAR for the Yankees before being traded for Kevin Brown, and only 1.7 more in his career. Ted Lilly would put up 29.5 WAR and go to two All-Star games after leaving New York.)

Many of Cashman’s defenders will cite that despite the flaws, the teams from 2002-2008 won better than 90 games and reached the postseason six of those seven seasons. Again, allow me to push back a little on giving the GM credit for that run.

The offensive juggernaut of that stretch was comprised of players that were inherited from the previous regime (Jeter, Posada) acquired in salary dumps from other teams (Alex Rodriguez, Bobby Abreu) or simply purchased as free agents (Hideki Matsui, Gary Sheffield, Jason Giambi, Robinson Cano). There were no draft picks that panned out or stealthy trades that led to the relative success of that era – it was all either inherited talent or due (once again) to the owner’s checkbook, not the GM’s baseball acumen.

Let’s move forward to the 2009 Championship team, the Yankees only one in the past 20 seasons. If there is something for which Cashman doesn’t get enough credit, it’s the trade that landed, Nick Swisher in the Bronx. A high OBP, switch hitter with power who played three positions in exchange for nobody who’d ever be missed was a heist. That said, nobody would argue Swisher was the difference maker that turned the tide for the Yankees.

I think we’d all agree it was the free-agent signings of CC Sabathia, Mark Teixeira, and to a lesser extent, A.J. Burnett that pushed the Yankees over the top. I think we’d also agree that there wasn’t a GM in the offseason of 2008-2009 who wasn’t fully aware that CC and Teixeira were monsters and that Burnett was very good – but only one of them had the go-ahead to spend nearly a half a billion dollars on the three.

Then after going through another stretch of being good but not good enough from 2009-2012, the Yankees morphed into a team that won 80 something games each year from 2013-2016, despite being in the top five in payroll each season. That’s when Cashman’s defenders love to point to the roster fire sale “rebuild” that resulted in very good teams from 2017-2020. Finally, a stretch where some good trades were made and some players coming up through the organization panned out. Still, even Cashman’s staunchest supporters would agree, crediting him for the re-build is like crediting the arsonist for grabbing the fire extinguisher.

Despite the rebuild, Brian Cashman’s plan coming into the 2021 season was to have a total of zero shortstops on the 40-man roster who had proven they could play the position on the big league level, and exactly one reliable starting pitcher. This past season wasn’t a question of not meeting expectations as much as it was why were the expectations so high in the first place?

Also to be clear, since the turnaround in 2017, both Boston and Tampa Bay have two division titles each – the Yankees have one. The Red Sox have won a World Series and Tampa Bay has appeared in one (that would be zero, and zero for the Yankees if you’re scoring at home). The turnaround has only been another five-season stretch of good, but not good enough.

The end result is that over the past 20 seasons, the Yankees have won as many Championships as the Diamondbacks, the Angels, and the Marlins. Since the Yankees’ last World Series title 12 years ago, they have one fewer title and two fewer World Series appearances than the Kansas City Royals. (The Kansas City Royals.) Heck, even the Mets have been in the World Series more recently than the Yankees.

Don’t let the relative success of the Yankees under Brian Cashman fool you: It’s relative to the Pirates, Rockies, and Twins. The Yankees have been in a perpetual state of “good”, but not “good enough” for 12 years, and they’re going to stay that way until Hal Steinbrenner changes his feelings about Brian Cashman. Nobody is expecting that to happen of course, as Cashman did manage to put a team with a Pythagorean W/L of 86-76 on the field while staying under the luxury tax threshold this season, and those flags fly forever, baby.

If you’re a Cashman defender who wants to say there need to be changes with the coaching staff or manager, I wouldn’t argue too much. Yet to me, that would be what Yankees’ announcer David Cone refers to as “eyewash”. Cleaning house with the coaches is only treating the symptom – there needs to be an upgrade at the GM position if the Yankees are ever going to be great again.

As far as who Cashman should be replaced with, that’s a conversation for another day. However, I will point out that the Red Sox have changed GMs four times this century and all four have outperformed Cashman, so finding an upgrade can’t be that difficult.

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