MLB Draft: Examining Cherington's Boston classes

The 2020 MLB Draft will be held on June 10, and even though it is significantly shortened to just five rounds, it will provide general manager Ben Cherington his first real opportunity to restock the Pirates' farm system.

This isn't Cherington's first turn as a general manager, as he served as the Red Sox's GM from 2012-2015. He left Boston one of the strongest farm systems in baseball in 2015. How many of those top prospects came from the draft?

FIRST ROUND PICKS

2012, Pick 24: SS Deven Marrero

2012, Pick 31: LHP Brian Johnson

2012, Pick 37: RHP Pat Light

Marrero was considered a potential top-10 pick heading into his junior year, flashing solid field, throw and run tools. The bat was the only concern, and he ended up slumping in his junior year at Arizona State. The Red Sox still drafted him 24th overall, and Marrero did eventually make the majors and play parts of three seasons with them. He just was never able to hit Major League pitching and has bounced around as a replacement-level backup the last couple years. The Red Sox were able to trade him for lefty reliever Josh Taylor, who turned in a quality season in 2019.

The Red Sox also had two compensation first-round picks this draft after losing Jonathan Papelbon and Jacoby Ellsbury in free agency. Johnson was one of the best players for some good Florida Gators teams and was considered one of the best collegiate lefties in the draft. He battled injuries and anxiety in his professional career but has finally become a part of the Red Sox's pitching staff, providing middle relief and the occasional spot start.

Light was a bit of a stretch at 37th overall, with most draft experts pegging him to be about a third-round pick. That stretch was understandable though since the Red Sox had to sign three first rounders. Light had the frame and a mid-90s fastball, but he was never able to consistently repeat his mechanics and left too many pitches over the plate. Still, his stuff was good enough for him to reach the majors in 2016, and the Red Sox ended up trading him for bullpen help. Light drifted through the minors for a few years -- including passing through the Pirates organization in 2017 -- before hanging it up.

2013, Pick 7: LHP Trey Ball

Ball was one of the most-hyped high-schoolers in the 2013 draft, showing a plus fastball and breaking pitch. He was the type of projectable pitcher scouts go for, so few were surprised when the Red Sox took him seventh overall. Ball never had much success in professional ball though, struggling with his delivery and control. His pedigree got him to AA, but that's as far as his first-round promise could take him. There was a brief experiment to turn him into a two-way player in 2019, but the writing is on the wall for his career.

2014, Pick 26: SS Michael Chavis

2014, Pick 33: RHP Michael Kopech

Chavis was the only high school position player the Red Sox selected in the first round under Cherington. He struggled for the first two and a half years in the minors, not really finding a groove until he reached A+ ball. It looked like he might be a bust for a while, but he was finally able to start to translate some of that raw power into game situations. He clubbed 18 home runs in his rookie season last year, and now he is being considered as the future long-term second baseman for the Red Sox.

Kopech was another projectable high school arm like Ball, but he panned out. He was traded to the White Sox as part of the Chris Sale trade after the 2016 season, and he has become one of the top pitching prospects in the game. MLB Pipeline has him ranked as the 20th best prospect in baseball. Kopech really broke out in the White Sox's system, and even after missing 2019 recovering from Tommy John surgery, he has one of the most dynamic fastballs for any starting pitcher prospect.

2015, Pick 7: OF Andrew Benintendi

The Red Sox signed Hanley Ramirez and Pablo Sandoval the previous offseason, losing picks in the process, so they needed to nail their first-round selection. They did, getting arguably the best collegiate player in the draft with the seventh overall pick. While Cherington's successor, Dave Dombrowski, traded most of the prospects he inherited, Benintendi was the one he was not willing to trade. So far, Benintendi has justified that faith, posting 10 career WAR and finishing second for the 2017 Rookie of the Year vote. His 2019 breakout did not go as planned, but he has another gear.  If he finds it, he will be one of the game's best left fielders.



OTHER NOTABLE PICKS

2012: RHP Ty Buttrey, 4th round; RHP J.B. Wendelken, 13th round

While Buttrey and Wendelken have become good MLB relievers, neither suited up for the Red Sox. Wendelken was traded to the White Sox in 2013 as part of the Jake Peavy trade, and Buttrey went to the Angels in 2018 for Ian Kinsler. The Red Sox won the World Series both of those years, so the trades are easy to justify.

The Red Sox drafted and signed four other players who reached the majors briefly: Second-round RHP Jamie Callahan, third-round RHP Austin Maddox, sixth-round RHP Justin Haley, and ninth-round SS Mike Miller. It's also worth mentioning the Red Sox selected RHP Carson Fullmer and 3B Alex Bregman in the later rounds too but did not sign either.

2013: SS Carlos Asuaje, 11th round

This is clearly Cherington's worst draft with Boston. They drafted and signed just four future Major Leaguers this year, and only one, ninth-round pick RHP Kyle Martin, ever played for the Red Sox. Even then, he pitched just 2.1 innings for them.

Asuaje was sent to the Padres as part of the deal for closer Craig Kimbrel during the 2015 offseason. Their 19th-round pick, LHP Gabe Speier, went to the Tigers as part of the Yoenis Cespedes, Rick Porcello deal, and 26th-round SS Mauricio Dubon was traded alongside Travis Shaw to the Brewers for Tyler Thornburg.

2014: 1B Sam Travis, 2nd round; LHP Jalen Beeks, 12th round

The Red Sox did their best work this year in the first round with Chavis and Kopech. At one point it looked like Travis was going to be the Red Sox's first baseman of the future, but he never got a hold of Major League pitching. He was designated for assignment this offseason and was later traded to the Rangers.

Beeks was traded to the Rays in 2018 for eventual postseason hero Nathan Eovaldi. He should be a reliever going forward. RHP Chandler Shepherd, a 13th round pick, was claimed off waivers twice last year and finally made his MLB debut with the Orioles.

2015: LHP Logan Allen, 8th round; LHP Bobby Poyner, 14th round

The real winning pick was Benintendi in the first round, but Allen is a close second, even though he barely spent time in the Red Sox's farm system. He was part of the package for Kimbrel, and the Padres developed the high school lefty into a top-100 prospect before trading him to the Indians. He was roughed up a bit in his first year in the majors, but that's hardly a cause for alarm.

Poyner had a down year in 2019, but still looks to be a part of the Red Sox's future bullpen plans. Three other right-handed pitchers -- sixth-round pick Travis Larkins, seventh-round pick Ben Taylor and 36th rounder Trevor Kelley -- have also made it to the majors.

TAKEAWAYS

It would have been interesting to see what would have come of some of these draft picks if Dombrowski been patient with some of these prospects. The Red Sox are currently thin in the rotation, so a young stud like Kopech or Allen could have gone a long way.

The only truly poor draft out of these is the 2013 one. None of their top eight picks even made it to the majors, and the players they dealt were more auxiliary parts than centerpieces. While there wasn't a future All-Star in their 2012 draft class, they did draft and sign nine future Major League Players, two of whom were traded for key players on World Series-winning teams. It would be hard to call that a bad draft

Cherington went 3-3 with his first-rounders the last two seasons. Kopech and Benintendi might end up being two of the best at their respective positions in a year or two, Chavis will be at least a good utilityman.

Cherington left the Red Sox one of the best farm systems in the game upon his departure in 2015. A large percentage of those highly-rated prospects came from the draft, but they also found success in the international market and making trades. He will need to do the same to build up the Pirates' farm system.