Red Sox: Best and Worst MLB Drafts of this century

Apr 18, 2017; Toronto, Ontario, CAN; Boston Red Sox catcher Christian Vazquez (7) shows the umpire the ball after a play at the plate in the first inning against the Toronto Blue Jays at the Rogers Centre. Mandatory Credit: John E. Sokolowski-USA TODAY Sports
Apr 18, 2017; Toronto, Ontario, CAN; Boston Red Sox catcher Christian Vazquez (7) shows the umpire the ball after a play at the plate in the first inning against the Toronto Blue Jays at the Rogers Centre. Mandatory Credit: John E. Sokolowski-USA TODAY Sports
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Since 2000, the Boston Red Sox have had some great drafts, and some that hope to be forgotten. Here are some highlights and lowlights.

May 24, 2017; Boston, MA, USA; A general view of Fenway Park as the sun sets during the fourth inning of the game between the Boston Red Sox and the Texas Rangers. Mandatory Credit: Greg M. Cooper-USA TODAY Sports
May 24, 2017; Boston, MA, USA; A general view of Fenway Park as the sun sets during the fourth inning of the game between the Boston Red Sox and the Texas Rangers. Mandatory Credit: Greg M. Cooper-USA TODAY Sports /

Over the last 17 years, the Boston Red Sox have been blessed with four of the game’s best General Managers. Dan Duquette, Theo Epstein, Ben Cherington, and Dave Dombrowski have all molded this franchise in their likeness.

Their collective ideas have brought three World Series titles to Boston, and have helped to redefine the culture and stigma of the Red Sox. One major way they did that was through the use of the MLB Draft.

The MLB Draft is inherently unlike the other sports of the “Big 4”. It takes years for players to break into the majors, and it might take years after that for them to reach their peak. It is very different from the NBA, where top draft picks sometimes turn into a top 10 player in the league in their rookie year.

Perfect example: the best draft since 2000 took over five years to really show the value of that draft. For the sake of this post, no draft past 2014 will be able to make the list. It is just too early to decide if that was a great or horrible draft. Sorry, Andrew Benintendi.

While there was a clear cut best and worst draft since 2000, there were some honorable mentions on both sides. To start, let us look at the two drafts that finished just behind the best draft.

Oct 10, 2013; Boston, MA, USA; Boston Red Sox general manager Ben Cherington watches the team during a workout in preparation for the American League Championship Series at Fenway Park. Mandatory Credit: Greg M. Cooper-USA TODAY Sports
Oct 10, 2013; Boston, MA, USA; Boston Red Sox general manager Ben Cherington watches the team during a workout in preparation for the American League Championship Series at Fenway Park. Mandatory Credit: Greg M. Cooper-USA TODAY Sports /

Best Honorable Mentions

Judging the success of a draft years after it happens is a little unfair, but so are many other things in professional sports. In baseball especially, one or two big drafts and you can change the direction of your franchise. Both positive and negative, who you choose in the draft can be very important.

Since 2000, the Red Sox have had some very good drafts. One that comes to mind is 2014. The final draft that was spearheaded by former GM Ben Cherington, the 2014 draft has already reaped some rewards for Boston. Three of the top 10 prospects in the system were drafted just three years ago.

Michael Chavis, who is having a breakout season in Salem, was Boston’s first pick. Josh Ockimey, a first baseman who is continuing his 2016 success, was taken in the 5th round. Finally, this draft has seen a player make a major league impact, as Sam Travis (2nd round pick) looked great in his two week long stint in Boston. And that is without mentioning a key piece to the Chris Sale trade, first round pick Michael Kopech.

The 2005 Draft was not too shabby, either. Jacoby Ellsbury was the 1st pick by the Red Sox, and he proved to be a valuable member of two championship teams. Clay Buchholz was someone who was marred by inconsistency in Boston, but was a very solid draft pick. Jed Lowrie, while not having the best career, has been an everyday player for multiple years in the majors. Having to progress through many levels of professional baseball, Lowrie has served as a solid veteran.

But, these drafts pale in comparison to what has been the best Red Sox draft in recent memory. When you look to the mastermind behind it, it is no surprise.

May 30, 2017; Chicago, IL, USA; Boston Red Sox right fielder Mookie Betts (50) celebrates his home run in the dugout in the second inning against the Chicago White Sox at Guaranteed Rate Field. Mandatory Credit: Patrick Gorski-USA TODAY Sports
May 30, 2017; Chicago, IL, USA; Boston Red Sox right fielder Mookie Betts (50) celebrates his home run in the dugout in the second inning against the Chicago White Sox at Guaranteed Rate Field. Mandatory Credit: Patrick Gorski-USA TODAY Sports /

2011 Draft

Ah, the 2011 Draft. It has become almost commonplace to know how amazing this draft is, as it is mentioned at least once a week on the broadcast. Why is that? For one, it was the final draft made by the greatest GM in the history of baseball. That would be none other than Theo Epstein, otherwise known as “The Curse-Breaker.”

Let’s look at some of these picks. We cannot start the discussion about the 2011 Draft without mentioning the 172nd pick. Mookie Betts somehow was a 5th round pick, and all he has done is been one of the best young players in all of baseball. Just five years after being selected in the 5th round, Betts was the runner-up for the AL MVP award.

Everyone knows how great Betts is, but who else makes this draft great? Two teammates of Betts were taken in the 1st round in 2011. Matt Barnes, the former UConn standout, has been a solid piece of the bullpen this year. Also, Jackie Bradley was another 1st round selection. Being one of the best defensive outfielders in baseball, it is safe to say Epstein made the right selection.

What truly makes this draft amazing is the multitude of talent. The Red Sox ended up having four first round picks as compensation for losing Victor Martinez and Adrian Beltre in free agency. Blake Swihart was yet another first round selection by Boston, and has been blocked from being a part of the Boston Red Sox.

Also, Epstein found even more value in the 9th round. Travis Shaw was taken out of Kent State University, and turned into being a good major league player. Currently a member of the Milwaukee Brewers, he is having a career year. At the very least, he contributed stability at the hot corner last year for Boston, and having one of the best nicknames of all time.

Apr 18, 2017; Toronto, Ontario, CAN; Boston Red Sox catcher Christian Vazquez (7) shows the umpire the ball after a play at the plate in the first inning against the Toronto Blue Jays at the Rogers Centre. Mandatory Credit: John E. Sokolowski-USA TODAY Sports
Apr 18, 2017; Toronto, Ontario, CAN; Boston Red Sox catcher Christian Vazquez (7) shows the umpire the ball after a play at the plate in the first inning against the Toronto Blue Jays at the Rogers Centre. Mandatory Credit: John E. Sokolowski-USA TODAY Sports /

Worst Honorable Mentions

While there have been some great drafts for the Red Sox, some have been not so pleasant. In general, player development is one of the hardest jobs to do in professional sports. Not every draft is going to have the next Ken Griffey Jr. or Mike Trout.

The 2001 draft was the last draft of former GM Dan Duquette. While Duquette laid the groundwork for what became the 2004 World Series Championship team, he whiffed on this draft. The only player of relevance was Kevin Youkilis. While Youk was great at getting on base, he was average for most of his career. The first pick by Boston was Kelly Shoppach, who was a below average catcher at best.

The 2nd pick was Matt Chico, a high school pitcher out of California. If you have never heard that name, it is because he never signed with Boston. He made appearances for the Nationals, but barely had a cup of coffee in the majors. Also, four of the next five picks made by Boston did not ever make the majors. The one that did? He didn’t sign with Boston.

Also, the 2008 Draft was not one for the record books. The only reason this did not make the worst draft since 2000 is because of one player: Christian Vazquez. Other than him, this draft is filled with “what could have been”.

Casey Kelly and Ryan Lavarnway were two highly touted prospects who never amounted to their expectations at the MLB level. Both players were seen as impact players one day, but never developed into that. Also, an outside force derailed another player’s career.

Ryan Westmoreland, a Rhode Island native, was drafted out of high school because he has all the tools of a major league player. After seeing some success in the low levels of the minors, a brain tumor sidelined him for the rest of a season. The tumors kept coming back, and Westmoreland was forced to retire from professional baseball. In a class act, the Boston Red Sox promised to help Westmoreland with his medical expenses.

But, there is one more draft that was something to forget for the Boston Red Sox.

May 28, 2017; Boston, MA, USA; A general view of Fenway Park from inside of the green monster score board prior to a game against the Seattle Mariners at Fenway Park. Mandatory Credit: Bob DeChiara-USA TODAY Sports
May 28, 2017; Boston, MA, USA; A general view of Fenway Park from inside of the green monster score board prior to a game against the Seattle Mariners at Fenway Park. Mandatory Credit: Bob DeChiara-USA TODAY Sports /

2009 Draft

After reading about the 2008 Draft, it does not seem possible that a draft could get worse. But, only one year later, the Red Sox had one of the worst drafts in their history.

What made the 2009 Draft so terrible was just like the draft one year prior: a lack of talent. Yes, the 2009 Draft had Stephen Strasburg, AJ Pollock, and Mike Trout. But by the time the Red Sox picked at pick 28, the talent was all gone.

Their first selection was Rey Fuentes, who never played a game for the Boston Red Sox. While he still had value, he was dealt with Casey Kelly and Anthony Rizzo to San Diego for Adrian Gonzalez.

Fuentes has played in only 55 games over three seasons in the majors. And while hindsight is 20/20, the Red Sox passed up on James Paxton and Garrett Richards.

Jeremy Hazelbaker is another prospect who never lived up to any hype he had. Hazelbaker was a college player who was drafted in ’09, but did not make his MLB debut until last year. And hitting .235 in over 100 games, he has not fared well in his small sample size.

Sadly, he was the 2nd best player the Red Sox drafted. The first? Alex Wilson, current reliever for the Detroit Tigers. You know, the Tigers, the team that has been notorious for having a well below average bullpen.

Next: Who will Red Sox draft in the first round?

Wilson’s career ERA is 2.86, and that is factoring in a year where he had a 1.91 ERA. For a reliever, his ERA is pretty high, especially for someone in high leverage situations. While Theo Epstein hit on most of the drafts during his time in Boston, this was the backend of a two-year stretch where he guessed wrong on many prospects.

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