What If the Red Sox Hit a Home Run in the First Round of Every MLB Draft From 2010 Until 2017?

Late last month, Major League Baseball and the MLB Players Association reached an agreement to cut down on spending in what will likely be a shortened 2020 season due to the COVID-19 pandemic impacting millions across the country and world.

Among the topics covered in said agreement was the 2020 amateur draft. According to Baseball America’s J.J. Cooper, this year’s draft “will be cut to no fewer than five rounds (MLB can expand it if it so chooses and several scouting departments hold out hope that it could be expanded to 10 rounds). The draft will be held as early as the current June 10 start date and as late as July 20.”

Since 2012, the draft has consisted of 40 rounds, so up to 7/8ths of this year’s draft-eligible prospects could go undrafted if the 2020 draft is indeed only five rounds.

The Red Sox have been a team that has found success in the later rounds of the draft in recent years, so this cutback only means that they will have to be more spot on with the limited picks they have this year.

That notion, as well as this recent article from The Athletic’s Jeff Howe, inspired me to look back at past drafts and ponder what could have been for the Sox if they were perfect, or nearly perfect, in the process.

For simplicity’s sake, we’ll stick with just the first round and begin with the 2010 amateur draft. Let’s get to it.


Round Pick No. Actual Pick ‘Perfect’ Pick
1 20 Kolbrin Vitek, 3B Christian Yelich, 1B
1s 36 Bryce Brentz, OF Noah Syndergaard, RHP
1s 39 Anthony Ranaudo, RHP Nick Castellanos, 3B

Analysis: Vitek never made it past Double-A, Brentz has not appeared in a major-league game since 2016, and Ranaudo has been out of professional baseball for three years.

On the flip side, Yelich, who went to the Marlins with the 23rd overall pick in 2010, has emerged as one of the best outfielders in baseball and has finished first and second in National League MVP voting the past two seasons with the Brewers. Syndergaard, who went to Toronto with the 38th overall pick, has been solid with the Mets, while Castellanos, who went to Detroit with the 44th overall pick, earned himself a four-year, $64 million contract with the Reds back in January.


Round Pick No. Actual Pick ‘Perfect’ Pick
1 19 Matt Barnes, RHP Mookie Betts, 2B
1 26 Blake Swihart, C Trevor Story, SS
1s 36 Henry Owens, LHP Blake Snell, LHP
1s 40 Jackie Bradley Jr., OF Mike Clevinger, RHP

Analysis: Barnes was far from a poor pick at No. 19 in 2011, but if Theo Epstein and Co. could do it all over again knowing what they know now, I’d assume they’d jump on the chance to take Betts early instead of waiting for the fifth round like they originally did.

Swihart and Owens, meanwhile, own career bWAR’s of -0.3 and 0.1 respectively. Since they were still on the board at the time Swihart and Owens were selected, Story, who has won Silver Slugger awards in each of the last two seasons with the Rockies, and Snell, who despite struggling last year is still a Cy Young Award winner in his own right, would have been better picks in hindsight.

As for the Sox’ last pick of the first round in 2011, Bradley Jr. was a pretty solid choice out of the University of South Carolina, but given how much the Sox have struggled to develop starting pitching, Clevinger, who posted a 2.49 FIP with the Indians last year, probably would have been the way to go.


Round Pick No. Actual Pick ‘Perfect’ Pick
1 24 Deven Marrero, SS Alex Bregman, 2B
1s 31 Brian Johnson, LHP Matt Olson, 1B
1s 37 Pat Light, RHP Joey Gallo, 3B

Analysis: Marrero was regarded as one of the best infield prospects in the 2012 draft thanks to his glove. That defensive prowess stuck with him as he rose through the ranks of the Red Sox’ farm system, but he was really never able to put it together offensively.

Johnson was another well-regarded draft prospect, but he dealt with numerous on and off the field issues before making his major-league debut in 2015 and has since been taken off the Sox’ 40-man roster. It did look like he had a solid chance to make the team out of spring training before the league shut everything down, though.

As for Light, there’s not much to say, as he owns a lifetime 11.34 ERA over 17 major-league relief appearances between the Red Sox and Twins. He is a quality follow on Twitter, though, so I’ll give him that.

Turning to the ‘perfect’ picks, Bregman himself said he would have signed with the Sox if they took him with the 24th overall pick in 2012, but they didn’t. Instead, Boston took Bregman in the 29th round, and since he had already committed to LSU, the New Mexico native went the college route instead.

Olson and Gallo, meanwhile, were not taken off the board until the former was taken by the Athletics with the 47th overall pick and the latter was taken by the Rangers with the 39th overall pick.


Round Pick No. Actual Pick ‘Perfect’ Pick
1 7 Trey Ball, LHP Aaron Judge, OF

Analysis: Trey Ball, man. Oof. The first left-handed pitcher taken off the board in 2013 never made it past Double-A and even tried to resurrect his career as an outfielder before his minor-league contract expired at the conclusion of last season.

Besides the Cubs’ Kris Bryant, the best player taken in the first round of this draft to this point in time has been none other than Yankees slugger Aaron Judge, who has mashed 110 home runs in his first 396 games in the majors. Would have been nice.


Round Pick No. Actual Pick ‘Perfect’ Pick
1 26 Michael Chavis, SS Jack Flaherty, RHP
1 33 Michael Kopech, RHP Brian Anderson, 3B

Analysis: Chavis just made his major-league debut last April, while Kopech was a key piece in the blockbuster trade that sent Chris Sale to Boston back in 2017. It’s still too early to say where those two stand in terms of their paths to big-league relevancy. But, Flaherty emerged as a legitimate ace during the latter half of the 2019 campaign with the Cardinals and is still just 24 years old. Anderson, meanwhile, slashed .261/.342/.468 over 126 games with the Marlins last year.


Round Pick No. Actual Pick ‘Perfect’ Pick
1 7 Andrew Benintendi, OF Walker Buehler, RHP

Analysis: As big of an Andrew Benintendi guy as I am, it’s pretty crazy that Walker Buehler was not off the board until the Dodgers took him with the 24th overall pick in 2015. It just goes to show how good Los Angeles is at drafting and developing their own talent.


Round Pick No. Actual Pick ‘Perfect’ Pick
1 12 Jay Groome, LHP Pete Alonso, 1B

Analysis: Groome has pitched in just 20 professional games since signing with the Red Sox in July 2016. He missed the entire 2018 season due to Tommy John surgery and he appeared in three games between the GCL Red Sox and short-season Lowell before last year’s minor-league campaign came to a close. He is still just 21 years old though, and is still ranked by MLB Pipeline as the Sox’ No. 7 overall prospect.

That is certainly encouraging, but after the season rookie first baseman Pete Alonso just put together for the Mets, where he crushed a record-setting 53 home runs and drove in 120 runs over 161 games last year, that certainly appears to have been the pick to make.


Round Pick No. Actual Pick Perfect’ Pick
1 24 Tanner Houck, RHP Nate Pearson, RHP

Analysis: Houck is developing at a solid pace and it looks like he’ll open the 2020 minor-league season, if there is one, as a member of the PawSox’ starting rotation.

Pearson, however, was taken by the Blue Jays shortly after the Sox selected Houck and has emerged as one of the brightest pitching prospects in all of baseball thanks in part to having a 100+ MPH fastball at his disposal.

Neither Houck or Pearson have made it to the majors yet, but as far as projections go, those seem to be favoring the 23-year-old Pearson rather than the 23-year-old Houck.

Pitchers: Noah Syndergaard, Blake Snell, Mike Clevinger, Jack Flaherty, Walker Buehler, Nate Pearson

Catchers: None

Infielders: Trevor Story, Alex Bregman, Matt Olson, Brian Anderson, Pete Alonso

Outfielders: Christian Yelich, Nick Castellanos, Mookie Betts, Joey Gallo, Aaron Judge

16 players total, 10 All-Stars, two MVP Award winners, one Cy Young Award winner, one top pitching prospect, and no catchers.

It’s far from a complete roster, but it’s certainly a great place to start in terms of building through the draft.

Of course, the MLB draft is regularly regarded as a lottery, so it’s virtually impossible for any club to draft this well in a single year. This isn’t to say that this is how I expect the Red Sox to draft under chief baseball officer Chaim Bloom in the future, I just thought it would be fun to look back and go back in time to a certain extent. And you know what? It was fun.

Author: Brendan Campbell

Blogging about the Boston Red Sox since April '17. Also support Tottenham Hotspur.

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