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Reviewing the first rounders of the Ben Cherington and Dave Dombrowski eras

How’d they work out?

MLB: Baltimore Orioles at Boston Red Sox Bob DeChiara-USA TODAY Sports

iThe head of the Red Sox front office, whether it was General Manager or Director of Baseball Operations or now Chief Baseball Officer, has had a lot of turnover over the last decade. Theo Epstein held the reins for a long stretch in the aughts, but the team has had three more in the position since he left at the end of the 2011 season. With this in mind, I thought it would be a good exercise to compare the first round selections for each and how those selections have (or have not) led to four championships since 2004. First, I asked the Twitter-sphere which GM they preferred and Theo got the overwhelming majority of support.

Keep in mind, the pre-2013 draft was a very different beast. During that time, free agents were put into one of three buckets: Type A (player ranked in the top 20% of players at his position, Type B (player ranked between 20% and 40% at his position), and then everyone else. Last week, I reviewed all of Theo Epstein’s picks and will now move to the Ben Cherington and Dave Dombrowski eras.

Ben Cherington had been with the Red Sox organization since 1999 when he was an area scout. He moved his way up the ranks in the front office and became co-general manager when Theo Epstein left the team for a brief time in late 2005. After Epstein’s return. Cherington became vice president of player personnel. Theo left the team for a job with the Chicago Cubs in 2011 and Cherington was back in the driver’s seat. The 2012 season was a downright disaster but Cherington pulled off the Nick Punto Trade that offloaded a great deal amount of salary, which he then used to rebuild the team with a rag-tag team filled with veterans which, as you know, won it all in 2013. Let’s look back at his first rounders first.


Devin Marrero (24th)

Brian Johnson (31st)

Pat Light (37th)

The Red Sox lost another big piece from their 2007 core when Jonathan Papelbon left for the Phillies after the 2011 season. As compensation, they received the 31st and 37th overall picks, which they used to draft Brian Johnson and Pat Light, respectively. Johnson was named an All-American during his freshman year at Florida and served as their second or third starter during his sophomore and junior years. He was a semifinalist for the John Olerud Award in 2011, when he hit .405 and had a 6-4 record in 14 starts. After being drafted, he was assigned to Lowell. His season was quickly over after being hit in the hit with a come-backer that broke orbital bones in his face. The team moved him up the ranks quickly and he made his major league debut in 2015.

By the 2012 draft, Pat Light was rated as the 53rd prospect in Baseball America’s Top 100 for the class, so seeing him come off the board with the 37th pick was a bit surprising. He struggled as a starter and was moved to the bullpen after making just 49 starts over three seasons. He did make it to Boston late in the 2016 season for only 2.2 innings and was traded that offseason to the Twins for Fernando Abad.

Deven Marrero was a hitting machine during his time at Arizona State and the on the Cape, and the Red Sox snagged him with the 24th overall pick. He made his professional debut in Lowell where he posted a .268/.358/.374 line with 24 stolen bases. He was invited to Spring Training the next year and was the first Sox position player to receive an invite following the year he was drafted since Scott Hatteberg in 1991. Things were looking up for Marrero and he finished the year in Double-A. However, it wouldn’t last as Marrero was shuttled between Triple-A and the majors where we saw his performance struggle. Ultimately, he was traded to the Arizona Diamondbacks for Josh Taylor.


Trey Ball (7th)


In a surprising move, the Red Sox drafted Trey Ball, a left-handed pitcher slash outfielder from an Indiana high school. Ball led his team to a state championship as a two-way star during his senior year and was committed to the University of Texas but after being drafted in the first round and receiving a $2.75 million signing he signed with Boston. I cannot say I blame him. Unfortunately for the Sox, Ball was never able to throw strikes and flamed out in Double-A. He tried playing the outfield this past season but after playing in just five games in the GCL, his career with the Sox was over.


Michael Chavis (26th)

Michael Kopech (33rd)

Okay. That is much better.

Cherington went to the prep ranks again and selected Michael Chavis from Georgia with their first pick on the 2014 draft. He was assigned to the GCL and struggled out of the gate but finished his first professional season with a .269 AVG and helped the team snag a Gulf Coast League championship. His pathway to the majors was riddled with injury and a PED suspension in 2018. He began the 2019 season in Triple-A and after demolishing the ball to the tune of a .357 Isolated Power, was called up to the majors in April. He split his time between first and second base and is poised to do the same when baseball starts up again.

After the Yankees signed Jacoby Ellsbury, the Red Sox used their compensation pick to draft Michael Kopech. He was assigned to the Gulf Coast League for eight games before being shit down for the year. He moved to the South Atlantic League in 2015 where he was pitching well before being suspended for a banned substance. Then during the next spring training he broke his right hand during an altercation with a teammate. Even with the off the field issues, Kopech was an amazing talent on the mound. He had some of the highest velocity reading in the minors when he was with the Sox. His biggest contribution to the team, though, was being a part of the Chris Sale deal with the White Sox. He made his major league debut in 2018 but had to undergo Tommy John Surgery and was suppose to start games again this year.


Andrew Benintendi (7th)

MLB: New York Yankees at Boston Red Sox Bob DeChiara-USA TODAY Sports

After another last place finish the division in 2014, the Red Sox picked seventh in the draft the following summer. This time, however, they did not drop the ball (no pun intended) and selected Andrew Benintendi, an outfielder from University of Arkansas. He has always been a great hitter and he won the College Player of the Year and the Golden Spikes Award while at school. He made his debut at Lowell after being drafted and hit .290 in 35 games and moved up to Greenville where in he hit 0.351 in 19 games. Due to his advanced hitting skills, Benintendi moved quickly through the Red Sox system and made his debut with the club at the end of 2016.

After the Detroit Tigers released Dave Dombrowski in early August, he was named President of Baseball Operations in Boston later that month. Also during the press conference it was announced that Ben Cherington would step down as General Manager. With the Red Sox hiring him, it became quite clear that ownership was ready to win, and soon. Dombrowski was (and is) known for trading away younger talent for the chance to win it all. He did not waste time making that big trade when he acquired Craig Kimbrel from the San Diego Padres. Rather than that aspect of his career in Boston, though, we will look back at his drafts.


Jay Groome (12th)

Earlier in the spring of 2016, Groome was projected to be one of the first picks but fell to the Red Sox due to signabilty concerns and some off the field issues. After the two came to terms with a $3.65 million signing bonus, Groome was sent to the GCL where he threw four innings and then was sent to Lowell where he threw another 2.2 innings before being shut down. During Spring Training, he strained his intercostal muscle which caused his first full professional season to be delayed. After returning, he split his time between Lowell and Greenville, where he began to lose a little bit of his control and his walks stared to pile up. His season was over by August with the dreaded forearm soreness. He tried to ramp it back up the following year but had to undergo TJS in May 2018. He did not get back into a professional game until late last season and this year, in whatever form it may or may not come, will be a big test for Groome.


Tanner Houck (24th)

During his time with the Tigers, Dombrowski was known for taking high upside pitchers so seeing the Red Sox take a pitcher in the first round for the second year in a row was no big surprise. Houck had an amazing performance during Team USA competition and pitched well at Missouri. However, the team started to change his delivery and pitch mix soon after being drafted, but after the changes did not work he moved back to his college delivery. The team then transitioned him to the bullpen in 2019 for a possible call up to the majors but the Red Sox scuffled down the stretch and he was not called upon. During the Arizona Fall League, he moved back into a starters role and it was reported he was going to stay a starter during the 2020 season.


Triston Casas (26th)

With the 26th overall pick, the Red Sox selected Triston Casas, a prep corner infielder from Florida. Casas was impressive during his last year at American Heritage hitting .414 in 53 games and actually graduated a year early so he could be available during the draft. He only played in two games after bring drafted as he tore a ligament in his right thumb while playing third base. He was assigned to Greenville where he hit .254 but smacked 19 balls out of the park. He was slated to begin the year in Salem but a call up to Double-A was not out of the question this year. Casas is looking like the first baseman of the future for the Red Sox.



After surpassing the luxury tax threshold, the Red Sox did not have a first round pick during the 2019 season. Cameron Cannon and Matthew Lugo were their two selections in the second round.

After reviewing all three general managers first round selections, I feel the Dombrowski era lacks the love it deserves. All three players should make it to the majors at some point, with the only wild card in that picture being Groome. That is based on health and not lack of talent, though. There were some questionable picks during the Cherington era and later half of the Epstein era that, to my surprise, led me to think Dombrowski had the best first round selections, though obviously time will tell on that. What do you think?