Ranking Brian Cashman’s Draft Tenure as GM of the Yankees

brain cashmanBrian Cashman has 18 drafts under his belt as GM of the Yankees with a few gems, a few decent outcomes and a lot of bad results. While his trade history has been much more successful, Cashman has not always had a strong grasp on drafts, especially in the first half of his front office career.So which were the worst and which were the best?

First let’s start with the unquestionably lean years in the draft. The years you’d prefer to forget which are most closely associated to the Yankees’ extremely weak farm system through most of the opening decade to the 21st century.

1998-2002, 2007, 2010:

Here’s what you need to know about every player drafted in the five drafts from 1998-2002. Mark Prior was the most notable player selected and he never pitched for the Yankees. Prior was selected in the first round in 1998 as the Yankees’ second pick (43rd overall) and did not sign. Other than that, in five years, the Yankees only other notable players were: Andy Phillips (backup first baseman), Matt Smith (dealt in a package for Bobby Abreu), Shelley Duncan (an unforgettable month in the major leagues), Chase Wright (most notably remembered for giving up four consecutive home runs to the Red Sox in a game at Fenway), and Phil Coke (a failed starter for the Yankees who became a successful reliever for the Tigers for a short period of time. He was also part of the Curtis Granderson trade).

We can safely eliminate those years as the best in Cashman’s drafting tenure along with 2007 and 2010. Austin Romine, a third string catcher was drafted of note in 2007 and 2010 was Cito Culver, who never made it and was part of the aftermath of the Yankees’ losing plenty of picks for FA signings in 2009.

Next we can look at the unknown/competent but not great years:

2003, 2004, 2008, 2012 and 2015:

Tyler Clippard and Jeff Karstens were taken in 2003 with the former turning into a successful setup man (currently unsigned but part of the Mets’ 2015 playoff run) and the latter enjoying a couple of good years in Pittsburgh after a largely unsuccessful campaign in New York. Most notably, Karstens enjoyed a successful 2011 when he posted a 3.38 ERA as a starter before retiring after 2013 and a full year back in the minors.

Phil Hughes was taken in the first round of 2004 and had mixed results but was relied upon in the rotation for awhile and Mike Dunn out of the 33rd round has enjoyed some time as a successful lefty reliever for the Marlins.

In 2008, Gerrit Cole famously went unsigned as the first round pick and largely everyone else busted except David Phelps, who would be used in a trade with the Marlins last winter to acquire Nathan Eovaldi, a currently relied upon starter in the Yankees’ rotation. If Phelps were the only piece, this would rank higher.

Ty Hensley (first round) has not stayed healthy from the 2012 draft and Corey Black was traded out of the system, but there’s at least some faith Hensley can recover and become an important pitching prospect again. He will spend this season trying to bounce back from missing all of last season with Tommy John surgery.

This past year has a bunch of players who cannot properly be evaluated, but James Kaprielian seems promising if he can put together a healthy season in the minors.

So suffice it to say 12 out of 18 drafts have been largely worthless for Brian Cashman, which is noteworthy in itself but maybe not so uncommon, especially since there’s still a few lingering players who can become legitimate prospects.

Now we move into the years where Cashman can claim something tangible as a result. The drafts nobody will have a 30 for 30 on, but will remember with some level of fondness:

2005, 2011, 2014:

In 2005, Brett Gardner (3rd round) and Austin Jackson (8th round) were both selected. Gardner, as we know, has become one of the best Yankees’ position players since the core four to ever come out of the draft and remains the team’s left fielder. Jackson never played in New York, but was the centerpiece as a top prospect in the Granderson deal. While Gardner is a nice impact on the current roster and Granderson was an integral part of the team for a while, this still wasn’t an elite year.

Greg Bird and Brandon Pinder will both compete for roster spots either this year or next year. With Bird out for the season, he won’t be relevent again until 2017, but will be the favorite to take back first base given his debut in August of 2015 when he hit 11 home runs down the stretch for New York. Pinder will compete for one of the final roster spots this spring and can be a relied upon reliever in the future. They were both drafted in 2011.

Jacob Lindgren was the only pick or relevance in 2014 (unless Jacob Montgomery can emerge) and remains highly touted, very likely to claim a roster spot this spring as a lefty reliever.

So that leaves us with the contenders:

2006, 2009, 2013:

In 2006, the Yankees easily produced the most major league talent since the mid 90’s out of one draft. Ian Kennedy (1st round, 21st overall), Joba Chamberlain (first round, 41st overall), Zach McAllister (3rd round), Colin Curtis (4th round), George Kontos (5th round), Dellin Betances (8th round), Mark Melancon (9th round), Daniel Mccutchen (13th round), David Robertson (17th round) and Kevin Russo (20th round) all played in the majors at some point. At face value, it seems like an incredible haul and it was certainly above average.

But we can eliminate, McAllister, Curtis, Mccutchen and Russo, none of whom amounted to anything particularly substantial and you don’t get bonus points for producing fringe MLB players for other teams.

Chamberlain was certainly a vital part of the team in 2007 and 2008 and enjoyed seven years in the Bronx, but never reached his ceiling as a starter or reliever after a magical run in 2007. Even in Detroit and Kansas City, Chamberlain never regained setup man or closer talent.

Kontos threw six innings for the Yankees but has enjoyed the past four years as a successful Giants’ reliever, winning two titles in the process. He was traded for Chris Stewart when Romine went down with a back injury and has no impact on the current roster. Melancon has become a successful closer and setup man but never made it big in New York and was part of a Lance Berkman trade with no current impact on the roster.

The crown jewel and the only direct impact from the 2006 draft was Dellin Betances, who remains one of now a trio of monsters at the back of the Yankees’ rotation. Betances will spend at least six years in New York as one of the elite relievers in the game.

2013 is still loaded with promise and direct impacts. Eric Jagielo (1st round) was part of the Aroldis Chapman trade to form a second of the three headed monster in the back of the bullpen, Aaron Judge (1st round) is the top Yankees’ prospect and Ian Clarkin (1st round) has not stayed healthy but is still largely touted as a pitching prospect. Nick Rumbelow (7th round) will compete for a spot in the bullpen this year. This draft can potentially produce three major leaguers on the team in 2016 and 2017 and a fourth if Clarkin stays healthy.

But the best draft ever for Cashman happens to be the same year he had his best free agency shopping spree and the last time he won a title.

In 2009, the Yankees drafted Slade Heathcott (1st round), John Ryan Murphy (2nd round), Adam Warren (4th round), Caleb Cotham (5th round) and Bryan Mitchell (16th round).

Heathcott will likely never reach his ceiling but has reached the majors and shown promise. Injuries have derailed his career but he still has time to make it as a major league outfielder and is still under control by the Yankees, likely to be the first man called up in case of outfield injury. Murphy was recently traded this winter for Aaron Hicks, who ironically is the fourth outfielder on the team with a ceiling of being an everyday outfielder, insurance in case Judge doesn’t pan out or if Gardner is traded or anybody gets injured.

Warren and Cotham were also traded this winter in a strange coincidence. Warren was the center piece of the Starlin Castro deal and Cotham was the other somewhat notable prospect of the Chapman deal. Warren enjoyed time on the Yankees’ roster as a successful spot starter and reliever before being traded.

This all means that the 2009 winter produced: Sabathia and Teixeira (through free agency) and pieces to acquire: Castro, Chapman, Hicks and Mitchell, all of whom are likely to be on the roster in 2016.

Six of the Yankees’ 25 man roster in 2016 can be traced back to the 2009 winter, four of whom from the draft, all playing reasonably important roles making it the most impactful one in Brian Cashman’s career, past or present.

Best Trades by Brian Cashman

Worst Trades by Brian Cashman


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