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Yankees History
·7 min read

Looking back on Brian Cashman’s starting pitching moves: 2008-2015

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This is part of a series where I’m looking at every major starting pitching move that Brian Cashman has made since 2000. Part 1 ended with the Yankees missing the playoffs for the first time since 1993. The Yankees were moving across the street into their new stadium in 2009 and another lackluster finish would be unacceptable. With this in mind, Cashman set out to fix the starting rotation for good. 

2008-09 Offseason: Signed CC Sabathia & A.J. Burnett

These two moves won the Yankees the 2009 World Series, period. Sabathia is the best signing Cashman has ever made. 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.

From 2009-2012, Sabathia was exactly the dominant, overpowering pitcher the Yankees paid big bucks for. Eventually, his workload caught up to him as his production dipped from 2013-2015. He re-invented himself into a finesse pitcher, proving to be an invaluable asset to the Yanks’ clubhouse and rotation including a huge start in a series-clinching ALDS Game 5 win in 2017.

CC Sabathia Belongs in the Hall of Fame - Views from 314 Ft.

Burnett’s Yankee career was a little more interesting. He went 13-9 with a 4.04 ERA in 2009 before pitching to an ERA over 5 in the next two seasons. Cashman sent him to the Pirates ahead of the 2012 season. Despite Burnett’s underwhelming track record, in my mind his contract was worth it for one reason: the 2009 postseason.

Burnett took a trio of no decisions in his first three playoff starts in ’09. He pitched well in the first two, followed by a poor outing in Game 5 of the ALCS. His most important start would come in World Series Game 2 against the Phillies, a must-win after the Yankees were dominated by Cliff Lee (who I’ll get to later) in the opening game. With the prospect of heading to Philly down 0-2, Burnett rose to the occasion, allowing just one run over seven innings and striking out nine en route to a 3-1 win. The rest is history, as the Yankees won it all.

Was Burnett a disappointment in New York? That’s more than fair to say. But his start in World Series Game 2 makes him forever cool in my book.

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The Yankees failed to win a championship in the 2010s. The decade was more defined by the moves Cashman didn’t make than the ones he did.

2009-10 Offseason: Roy Halladay Traded to Phillies

Halladay was one of the best pitchers of his generation. He also dominated the Yankees for years when he played in Toronto. Halladay went 18-7 with a 2.98 ERA in 38 games against the Bombers. Despite Halladay’s dominance, the Blue Jays were never able to get past the Yankees or Red Sox so they began shopping him at the 2009 deadline before ultimately trading him to the Phillies that offseason. Despite trying, the Yankees were unsuccessful in their pursuit of the Hall of Famer. Imagine prime Halladay and CC 1-2 at the top of a rotation? Would have been absolutely insane.

2010 Trade Deadline & 2010-11 Offseason: Cliff Lee

Of any move on this list, I would have to argue that this one was Cashman’s biggest mistake. Lee would have been a tremendous help in getting those 2010-12 Yankee teams over the hump. He also wouldn’t have been able to dominate them in the 2010 ALCS.

The Yanks won the 2009 World Series despite losing both games Lee started. However, his 8 shutout innings in Game 3 of the 2010 ALCS swung the series in the Rangers’ favor for good. The worst part is, Lee easily could have been in the Yankees’ dugout for that series.

As Stephen so eloquently outlined last week, Cashman had a deal in place with the Mariners for Lee, planning to send Jesus Montero, David Adams, and Zach McAllister to Seattle.

Seattle got cold feet at the last minute, worried about Adams’ medicals. The Mariners requested Ivan Nova or Eduardo Nunez to replace Adams, and Cashman countered with Adam Warren. The Mariners declined, traded him to the Rangers, and the rest is history. Obviously, hindsight is 20/20, but that’s the entire point of this blog. Bottom line: if Cashman pulls the trigger on the Lee deal then the Yankees, at a minimum, play the Giants for the 2010 World Series, and have a much better chance at the pennant in 2011 and ’12 as well.

2011-12 Offseason: Signed Hiroki Kuroda & Traded for Michael Pineda

Cashman traded for Pineda after his All-Star performance as a rookie in 2011. Ironically, they finally sent Montero to Seattle after the Lee deal involving him fell through in 2010. After acquiring him, Big Mike had shoulder issues and didn’t end up appearing in a game for the Yankees until 2014. The best way to describe Pineda’s Yankee career is schizophrenic. He showed flashes of greatness, then would look lost for long periods of time. He finished 2014 with a 1.89 ERA in 13 starts after again battling injuries, and posted ERAs in the 4s each of the next three seasons before the Yankees let him walk in free agency.

Ultimately, the defining moment of Pineda’s Yankee career is the above tweet. In an April game against the Red Sox, Pineda was ejected after being caught with pine tar on his neck. Pineda always had plenty of promise, but was never able to put it together as a Yankee.

Kuroda is one of the best moves on this list. Kuroda was a consistent veteran presence in the rotation during his three seasons in New York. He threw 200+ innings with an ERA under 3.35 in his first two seasons, followed by 199 innings and a 3.71 ERA in 2014. 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. He followed that with a tough loss in ALCS Game 2 against Detroit, in which he gave up just three runs in 7.2 innings pitched. He doesn’t get enough credit because he was on bad teams, but Kuroda was a very good Yankee.

2013-14 Offseason: Signed Masahiro Tanaka

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While Sabathia is undoubtedly the best move on this list, you can make a great case that Tanaka is #2. He was just 25 when he signed a seven-year, $155 million deal out of Japan before the 2014 season to become the Yankees’ new ace. Tanaka was a dominant pitcher in Japan, and proved to be the same with the Yanks. He began the season 11-1 with a 1.99 ERA and struck out 113 batters in 99 innings en route to being selected to the All-Star team. Unfortunately, Tanaka suffered a partially torn UCL that season, and many wondered if he would get Tommy John surgery. He didn’t, and would return late in the season.

Tanaka has adapted from the power pitcher he once was. Despite his tendency to occasionally get roughed-up in the regular season, Masa has been effective every year in pinstripes. However he has shown he’s well worth the money because of his playoff performances. In eight postseason starts, Tanaka is 5-3 with a 1.76 ERA. He’s proven to be the guy the Yankees can trust the most come October. With his contract expiring after 2020, we can only hope Cashman keeps Tanaka a Yankee for life.

2014-15 Offseason: Traded for Nathan Eovaldi

Cashman acquired Eovaldi (as well as Domingo German) from the Marlins prior to the 2015 season. 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. He would never pitch for the Yankees again, but that wouldn’t be the last they would see of him.

The 2013-16 Yankees were a pathetic group of aging veterans. They made the playoffs just once in four years — a Wild Card loss to the Astros. Everyone expected Cashman to rebuild. What no one expected, however, was for that rebuild to last just half a season. Check back for the third and final installment to see how Cashman has navigated the “Baby Bombers” era.