New York Yankees Analysis: Cashman’s pitching moves since 2000, the hits and the busts

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The New York Yankees general manager Brian Cashman is the longest-tenured general manager in all of baseball. He has made some amazing acquisitions and trades over his time with the Yankees, but he has also had some terrible misses. To refresh your memory before the 2019 season, he acquired DJ LeMahieu from the Colorado Rockies for one of his best successes ever.

Cashman started with the Yankees as a humble intern in 1986, he impressed George M Steinbrenner, and six years later, he was promoted to the Assistant General Manager.  From that time, he worked hand and hand with then-manager Buck Showalter and “Stick Michael,” building the Yankee dynasty of the late ’90s. He became general manager of the Yankees in 1998. Under his leadership, the New York Yankees have won four World Series championships and six American League pennants.

Today thinking of this Yankees team’s pitching needs, we look at Cashman’s record in finding the starting pitching needs for the Yankees and how successful he was.



1998: Orlando Hernandez

One of the first moves Cashman made after being named general manager in February 1998 was signing Orlando “El Duque” Hernandez when the right-hander defected from Cuba. He was a crucial part of the 1998 team’s dominant rotation as he went 12-4 with a 3.13 ERA in 21 starts.

2000-2001: Mike Mussina

Cashman’s first great acquisition was Mike “The Moose” Mussina from the Baltimore Orioles. This one move may have been Cashman’s greatest. Mussina pitched successfully for the Yankees for eight years, racking up a 123-72 record. He also won over then games in each of those years. He ended his career with a 20 game winning season in 2008.

2001-2002: Jeff Weaver

If Mike Mussina was one of his best moves, Jeff Nelson turned out to be not so much. Nelson was okay in 2002, but in 2003, he fell apart. It all went south in 2003, though, as Weaver went 7-9 with a 5.99 ERA. He later gave up a walk-off homer in Game 4 of the World Series against the Marlins.

2002-2003: Jose Contreras

Contreras’ overall stat line in ’03 was 7-2 with a 3.30 ERA, but he had a rough postseason, allowing seven runs in eleven innings across his eight appearances. He reverted to being a full-time starter in 2004 but didn’t fare well and was traded to the White Sox. The New York Yankees also acquired Jon Lieber, but he didn’t appear in a game in 2003 as an injury that caused him not to appear for the Yankees until 2004.

2003-2004: Kevin Brown

The 2003 offseason was one of the most difficult for Cashman as he lost both Andy Pettitte and Roger Clemens to the Houston Astros. He had to make up for the loss, so he traded for Kevin Brown and Javier Vazquez. Brown pitched well in 2004, going 10-6 but only had 22 starts due to frequent injuries, including the time he punched the wall in the dugout, breaking his hand. He won ALDS Game 3 before getting lit up in games 3 and 7 of the ALCS. He went 4-7 with a 6.50 ERA in 13 starts in 2005 before retiring.

Vazquez was actually an All-Star in 2004 before struggling down the stretch, going 14-10 with a 4.91 ERA. He got the win in relief in ALCS Game 3 before allowing the soul-crushing Johnny Damon grand slam in Game 7. Vazquez would again pitch for the Yankees in 2010. That stint did not go well. Oh, and back to Lieber; he was14-8 with a 4.33 ERA for the Yanks in 2004. He gave up 3 ER over 6.2 innings in a no-decision in ALDS Game 2 against the Twins. Lieber then won ALCS Game 2 against the Sox but took the loss in Game 6. Of the three pitchers mentioned, he was probably best for the Yankees. Whatever the case, all three were gone after the 2004 season.

2004-2205: Randy Johnson

After the huge collapse of the New York Yankees in the ALCS, the Yankees cleaned house. Brown retired from baseball, and Vazquez and Lieber were sent out to dry. Cashman hired the “Big Unit” Randy Johnson, Jeret Wright, and yes, Carl Pavano. Let’s get Pavono out of the way first. He was on the injured list more than the mound and was one of the Yankee’s greatest failures starting only 26 games over five years. Wright went 15-8 with a 3.28 ERA. He would make 40 starts over his two seasons in the Bronx, going 16-12 with a 4.99 ERA. Wright didn’t make it out of the third inning in his only postseason start, allowing four runs on five hits as the Tigers eliminated the Yankees in ALDS Game 4 in 2006.



Randy Johnson was a five-time Cy Young Award-winning and led the National League in strikeouts. Johnson was not nearly as good as a Yankee, posting ERA’s of 3.79 and 5.00 in his two seasons with them. The worst part was that he was an utter postseason failure in pinstripes. He got shelled for five runs in just three innings in ALDS Game 3 in ’05, and another five in Game 3 again in ’06. Considering he was hired to be a postseason killer, he was an utter failure with the Yankees.

2007: Kei Igawa

Cashman tried to repair the team in 2007; he did that by getting both Andy Pettitte and Roger Clemens back from Houston. He also hired Igawa; rather than bore you, he was one of the worst Yankee acquisitions of all time.

2008-2009: CC Sabathia and A.J. Burnett

This is like the tale of two cities, one of the best and one of the worst. Burnett never adjusted to playing for the Yankees in the big spotlight. In his first year, he went 13-9 with a 4.04 ERA in 2009 before pitching to an ERA over 5 in the next two seasons. He was rewarded by being sent to the Pittsburgh Pirates.

Outside of Mike Mussina, CC Sabathia was Cashmans best Yankee signing. He went 3-1 with a 1.99 ERA in five starts in the 2009 postseason, during which he was named ALCS MVP. He went on to pitch 11 seasons for the Yankees, making three All-Star teams, leading the league in wins twice, and pitching to an 8-4 record in the postseason. Sabathia was a huge Yankee favorite. In his later years, although not as good, he battled each and every time he hit the mound for the Yankees before retiring last year.

2011-2012: Hiroki Kuroda

After an amazing postseason performance, Cashman signed Michael Pineda was at best a wild story with the New York Yankees, being both brilliant but at the same time horrible. He would have tremendous performances followed by long stretches of misery. He started with a shoulder injury that prevented him from pitching until 2014. Upon his return, he had a 1.89 ERA in 13 games. He never pitched that well again, and the Yankees let him walk in 2018.

Hiroki Kuroda was a consistent veteran presence in the rotation during his three seasons in New York. Kuroda also fared well in the 2012 playoffs, taking a no-decision after firing 8.1 innings of two-run ball in Game 3 of the ALDS against the Orioles. Kuroda was a much better pitcher than the Yankees give him credit for. He played during the years the had some pretty stinky teams.

December 2011 also saw Cashman sign international free agent Luis Severino. The verdict is out of Severino as he recovers from Tommy John surgery. In 2018 he went 19-8 before the surgery. Severino could still be a Yankee great when he returns this season.

2013-2014: Masahiro Tanaka

If there is a toss-up as to the best pitchers on this list between Mussina and Sabathia, Masahiro Tanaka surely has to come in third place. Even with an almost immediate partially torn UCL, Tanaka has been one of the most dependable Yankee pitchers even though he was not the ace they thought they were getting. Up until the last two years, Tanaka and CC were the backbones of the Yankee rotation. Tanaka has not been the same pitcher in the past two years and doesn’t go deep into games. At the end of the 2020 season, the New York Yankees did not give him a qualifying offer to remain a Yankee. He isn’t worth near the $23 million he earned last season. That being said, he was good enough that the Yankee might be willing to take him back short term on a much-discounted contract.

2014-2015: Nathan Eovaldi/Domingo German

This could have been the biggest blockbuster move of Brian Cashman’s career, but two things went wrong. Eovaldi was a solid Yankee, going 14-3 with a 4.20 ERA in 2015 and 9-8 with a 4.76 ERA in 2016 before undergoing his second Tommy John surgery in August. The Yankees let him walk. After his recovery, he would continue an excellent career.

German is a different story. German would go on to be the best Yankee pitcher in 2019. He went 18-4 but was caught slapping his wife in public, breaking the MLB domestic violence protocol, and ended getting suspended for the remainder of the season while the MLB investigatory body looked at his case. He could have gotten over 20 wins and been a big asset in the postseason. Instead, he was suspended for 81 games, including the entire 2020 season.

2017 Trade deadline: sonny Gray

After being traded from the Oakland A’s, Gray was an immediate disaster under the bright lights of Yankee Stadium and a demanding Yankee fan base. In the remainder of the season, he went 4-7. He failed to make it out of the fourth inning in ALDS Game 1 in Cleveland. When Gray was available, so was aging Justin Verlander; the fact they went after Gray and not Verlander may haunt them forever.

Gray went with the Cincinnati Red where he was back with his old Vanderbilt coach. Out of the bright lights of New York, Gray blossomed. In the past two years, he has gone 16-11 with a 3.07 ERA. Some industry experts are predicting the Yankees may kick that tire again. Possibly under a new coach, Matt Blake, he could be a difference-maker.

2018-2019: Gerrit Cole

Shortly before Christmas 2018, a New York Yankee foursome of Cashman, Boone, Blake, and Andy Pettitte traveled to California bearing gifts. They came out of meetings with Gerrit Cole and his wife with one of the best pitching pickups of the decade. Gerrit Cole was a New York Yankee. In this first shortened season with the Yankees, he pitched well. However, for Cole, a season doesn’t make a career. He was signed for nine years; how that pans out only the future will tell.

2018: J.A. Happ and James Paxton

Let’s end the article here and not talk about them at all.

If you are trying to measure Brian Cashman’s performance, you have to remember it is not based on starting pitching alone. Cashman has also acquired Robinson Cano, Hideki Matsui, Giancarlo Stanton, Starlin Castro, Chad Green, Tommy Kahnle, Zack Britton, Nick Swisher, Bobby Abreu, Curtis Granderson, Didi Gregorius, DJ LeMahieu, among many others. The bottom like for Yankee fans is that the Yankees have not had a dominant starting rotation since 2009, the last time they won a World Series. This writer believes that if the don’t have a dominant pitching rotation they can not win in the postseason.