Recently I have gone through the exercise of re-drafting the Yankees in the 2000s and 2010s as a fun way to discuss “What If” scenarios.
What I’ve realized however is that the Yankees have not had many players they drafted make a big impact at the major league level — especially near the top of the draft. But how have they done compared to teams of their like?
Leveling the Playing Field
It’s not fair to compare the Yankees to a team like the Rays for a few reasons. One, Tampa consistently drafted high because they were a bad team for many years, and it took them until the late-2000s to become competitive (largely thanks to their drafting). Two, Tampa doesn’t spend in free agency so they don’t lose picks — if anything they gain picks through competitive balance and compensation rounds. Overall they have a greater quantity and higher quality draft picks than the Yankees.
Instead of comparing the Yankees last 20 drafts (I’m only going back to the year 2000 for this) to the entire league, I figured it’s fair to compare them to teams in their winning and spending league over that time.
Here are the top-10 teams in terms of winning since 2000:
NYY: 94 wins/season
Of those teams, only two are in the same spending class as the Yankees — the Red Sox and Dodgers. Since the luxury tax threshold was established in 2002, here are the teams that have paid the most in tax:
Note: These figures might be incomplete because I’m combining multiple sources that have different information. But it’s about right.
The numbers above are a little misleading because teams reset the tax to reduce the total amount paid. The Red Sox are 11 time offenders but somehow have paid less than the Dodgers, who are 5 time offenders. The Yankees have gone over the tax 16 times. No other team has exceeded more than 3 times.
Surprisingly the Angels have only gone over the tax threshold once, in 2004. I think of them as a high-spending team, but they’re really more of a stupid-spending team (see: Josh Hamilton, Albert Pujols, etc.). They spend at the top of their roster, but that’s it.
So for this exercise I’m going to look at how the Yankees, Red Sox, and Dodgers — three teams in a winning and spending class of their own — have performed in the draft since 2000.
The first thing I looked at was high-impact first or supplemental round picks. These are players taken with a top-50 pick and should be the best bets to make the majors and contribute significantly.
Phil Hughes (2004, #23 overall)
Aaron Judge (2013, #32 overall)
Jacoby Ellsbury (2005, #23 overall)
Clay Buchholz (2005, #42 overall)
Jackie Bradley Jr. (2011, #40 overall)
Andrew Benintendi (2015, #7 overall)
Clayton Kershaw (2006, #7 overall)
Corey Seager (2012, #18 overall)
Walker Buehler (2015; #24 overall)
All of those players except Benintendi have been All-Stars for the team that drafted them, and Benintendi is a solid player who has yet to enter his prime at only 24-years old so I’m including him in this group of first round successes. You may not like some of these players, but if they’re good enough to make an All-Star team then they’re a successful high draft pick in my opinion.
Boston has also had 12 high draft picks reach the majors in a Red Sox uniform and the Dodgers have had 8. Both teams have had many other first round picks make the majors with a different organization, for whatever that’s worth.
In addition to Hughes and Judge, the Yankees have had just 5 players drafted in the first or supplemental round make the majors. Ian Kennedy (stunk with the Yankees before being traded), Joba Chamberlain (had his career derailed by the Yankees overbearing development team), Bronson Sardinha (bust), Andrew Brackman (one of the failed Killer Bs) and Slade Heathcott (one great moment).
The Yankees having produced just two “great” players in the past 20-years from the first round is bad. I’m putting “great” in quotes because, while Hughes was not a bad pitcher for the Yankees, he certainly wasn’t great. But he did make an All-Star team and help them win a championship pitching out of the bullpen in 2009.
Boston and LA are not that much ahead of the Yankees when you look at it in terms of stars produced. It’s also fair to put Kershaw aside because he was a top-10 pick.
The biggest difference is the number of players who reached the majors. Some of the 12 players for the Red Sox and 8 for the Dodgers turned into nothing, but they at least developed through their minor league systems enough to get a crack. The Yankees have a really low batting average when it comes to high draft picks, but hopefully that trend is changing with players like Clarke Schmidt, Anthony Seigler, and Anthony Volpe.
Over the past 20-years the mid-rounds have produced many great players. For a team like the Yankees, Red Sox and Dodgers, this is where the magic happens because they aren’t always picking at the top of the draft.
I’m calling rounds 2 through 14 the “mid-rounds.” I’m distinguishing the 1st and 2nd rounds because so much emphasis is put on a team’s first pick. The spotlight falls-off after that.
Brett Gardner (2005, 3rd round)
Dellin Betances (2006, 8th round)
Both of those picks turned out excellent for the Yankees, but two players is not a lot.
They have also obtained a number of quality players (and countless frustrating middle relievers) that have helped win ball games over the years, including Tyler Clippard, Austin Jackson, Austin Romine, John Ryan Murphy, and Adam Warren.
Those players have provided depth and/or been traded for quality players, like Jackson for Curtis Granderson, Murphy for Aaron Hicks, and Warren for Starlin Castro.
If Jordan Montgomery (2014, 4th round) turns into the starting pitcher we all hope, that will be a great pick.
Some other notables include Kyle Higashioka, Tyler Wade, Jonathan Holder, and Greg Bird… kidding.
Everything considered that’s not bad, until you compare it to the Red Sox and Dodgers.
Kevin Youkilis (2001, 8th round)
Jon Lester (2002, 2nd round)
Jonathan Papelbon (2003, 4th round)
Mookie Betts (2011, 5th round)
The Red Sox have not had as many mid-rounders contribute but they have gotten far greater impact. They don’t win championships in 2007, ’13, and ’18 without those players.
Mookie is probably the one that stands out seeing as how he’s a consensus top-5 player in baseball, but Youkilis, Lester and Papelbon were all at the center of the Red Sox’s success in the mid-to-late 2000s.
Other lesser players Boston has developed from the mid-rounds include Justin Masterson, Christian Vazquez, Brandon Workman and Travis Shaw.
Los Angeles falls somewhere between the Yankees and Red Sox on mid-round success. They’ve had more successful players than the Yankees but have not produced the All-Star level players of Betts, Lester, Papelbon and Youk.
Matt Kemp (2003, 6th round)
Joc Pederson (2010, 11th round)
Alex Verdugo (2014, 2nd round)
Cody Bellinger (2013, 4th round)
So the Dodgers are kind of the mid-round outfielder whisperers. Kemp was on track to being a superstar but injuries derailed him once he signed a big contract. Pederson and Verdugo have been useful outfielders, the latter net Mookie Betts this off-season in a trade, ironically.
The big name on their list is Bellinger. Some people already consider him a top-5 player in the league. I’m not saying they’re wrong; he won Rookie of the Year and MVP in his first three seasons. In a way, they got a Mookie Betts equivalent in Bellinger out of the mid-rounds. The Yankees have not produced a player close to that level.
Cody Bellinger saves Ryu’s no hitter on Mother’s Day last year pic.twitter.com/eL9bvAAWDK
— Dodgers Nostalgia (@RetroDodgers) May 10, 2020
LA has also produced Edwin Jackson (almost every team in baseball can thank them), Dee Gordon, Jonathan Broxton, Matt Beaty and old friend/foe Nathan Eovaldi.
The MLB draft can be a crap-shoot, but sometimes crap hits. Once the 15th round comes, hundreds of players have been selected. If you hit on a player this late in the draft it’s a combination of luck and good developmental work.
It’s a pretty short list for each team, and the Yankees actually have had the most success in the late rounds.
Phil Coke (2002, 26th round)
David Robertson (2006, 17th round)
Shane Greene (2009, 15th round)
Josh Reddick (2006, 17th round)
Russell Martin (2002, 17th round)
It’s safe to say the Yankees are best at drafting relievers. In many cases they are failed starters, but either way Cashman has been able to get bullpen value over the years from the draft.
I understand this may be an imperfect way to measure draft success, but the draft is not an exact science. Another way you could do this is to add-up all the WAR drafted/produced and see where the Yankees rank (Guess what? I’m not going to do that.) Comparing the Yankees to the Red Sox and Dodgers makes sense to me, and when I look at the recognizable names drafted over the past 20-years, there’s no denying the Yankees are in a clear third place among these teams.
The Yankees are getting better however. They routinely get more value from international signings than the draft, but many of their recent high draft picks have exciting potential. And who knows what will come out of the mid-to-late rounds? Perhaps the’ll find their Mookie Betts or Cody Bellinger in the 5th round too.
Here are some names to keep an eye on for the 2020 draft, which will be unlike any other year.