The Red Sox system has seen it fair share of ups and downs since 2010. Most of their number one ranked prospects by Baseball America have reached the majors but once you take a step back, most of the impact players were not ranked number one. When I started this exercise, I was expecting to write about Mookie and Devers but to my surprise they never ranked number one on Baseball America’s Preseason List. Obviously, the biggest contributor to the Red Sox has been Xander Bogaerts but Yoán Moncada and Andrew Benintendi have both contributed to a World Series title, although in different ways.
2010 - Ryan Westmoreland
Ryan Westmoreland was the Gatorade Player of the Year for Rhode Island his junior and senior year of high school. He was committed to play at Vanderbilt University but the Red Sox were able to lure him away by meeting his $2 million demand in 2008. Westmoreland battled injury throughout his career. After it was discovered he had a torn labrum in his shoulder, which required surgery, he was forced to mostly DH duties during his first assignment to Lowell. In his debut, he put up an impressive .296/.401/.484 with seven home runs and 19 stolen bases. His season ended prematurely, however, has he suffered a broken collarbone after crashing into an outfield wall attempting to make a catch. Going into the 2010 season, Baseball America rated him as the 21st overall prospect and first in the Red Sox system. Sadly before the season began he began to experience overall body weakness which later was diagnosed as a cavernous malformation on his brainstem. He had brain surgery in March 2010 and attempted comebacks throughout the 2011 and 2012 seasons but had to undergo surgery again in 2012. He announced his retirement in 2013 and is currently coaching at UMass-Dartmouth. It is hard to articulate how sad to see a player with so much promise have his career end like it did.
2011 - José Iglesias
Already an accomplished player in Cuba, Iglesias along with another teammate, deflected from Cuba and established residency in the Dominican Republic. The Red Sox signed him to a four-year contract in September 2009. He was assigned to Double A- Portland to begin his career and scouts were raving about his supreme defensive abilities. He was hitting above .300 before being hit by a pitch that broke his finger. He played the majority of the 2011 and 2012 seasons at Triple-A Pawtucket but did see sometime in Fenway when Kevin Youkilis was slowed with a sore back. After Will Middlebrooks went on the DL in 2013, Iglesias was called up and went on a tear. He hit .420 to go along with an 18-game hit streak during his first 100 at-bats. Then, in a somewhat shocking move, Iglesias was moved in a three team trade to the Detroit Tigers for Jake Peavy. Peavy turned out to be a perfect addition, though, as the Red Sox went on to win the World Series. Iglesias spent the next five seasons in Detroit before moving on to Cinncinati last year. He signed a one-year deal with the Orioles this past offseason.
2012 - Will Middlebrooks
Will Middlebrooks was a two-sport star (football and baseball) during his high school days in Texas. He was drawing interest at some colleges to play either quarterback or punter. He was an also a dual threat on the diamond, playing shortstop as well as pitcher. He eventually moved to third base after the Red Sox drafted him in fifth round of the 2007 amateur draft. He was moved a level at a time and the Sox saw him improve at every level. His best season in the minors was the 2011 season in Double-A where he hit over .300 with 18 home runs and an impressive 136 wRC+. He was having another amazing season in Triple-A during the 2012 and was promoted to Fenway after the Sox placed Kevin Youkilis on the DL. Just like Iglesias, he hit the ground running by hitting 0.326 in his first 40 games. His performance lead to the trade of Youk to the White Sox for Zach Stewart and Brent Lillibridge. He struggled initially during the 2013 season and was demoted back to Triple-A to work on some adjustments at the plate. He later returned to the team and was in the infamous “obstruction” play with Craig Allen during the 2013 World Series. He never returned to the highs of the 2012 season and moved on to the San Diego Padres after the Red Sox signed Pablo Sandoval during the 2014 off-season. He played the next few seasons for the Padres, Brewers, Rangers, and Phillies before announcing his retirement in January last year.
2013 & 2014 - Xander Bogaerts
What is there really to say here. We all know Bogey. We all love Bogey.
2015 - Blake Swihart
Swihart was a three-sport star in high school and played shortstop and pitcher. As a pitcher, he was able to get his fastball in the mid-nineties but moved behind the dish as he preferred hitting. He played for Team USA in 2010 and flew up the draft rankings after hitting .448 during the tournament. Swihart was committed to the University of Texas but after being drafted 26th overall and receiving a $2.5 million signing bonus, he decided to sign with the Red Sox. He played six games after being drafted in the GCL and was promoted to Greenville in 2012. He moved steadily level by level and performed better each year. After a red-hot start to the season, as well as a Ryan Hanigan injury, Swihart made his debut during the 2015 season. He played in 84 games, hit .274 with a 93 wRC+ but his biggest criticism was his defense behind the dish. In 2016, after Vásquez returned from Tommy John, the Red Sox had him playing in left field. However, he season was cut short after he ran into a wall in left field and injured his ankle which required surgery.
Unfortunately for him, he was never really the same. He bounced around in the field, mostly filling in as a bat off the bench for the next couple of seasons before the Red Sox designated him for assignment April 2019. He was traded to the Diamondbacks for outfielder Marcus Wilson but Swihart never found his footing on the team and was designated for assignment again in August. He signed a minor-league contract with the Texas Rangers and looked poised to make the team before everything shut down this spring.
2016 - Yoán Moncada
After leaving Cuba in 2014, Moncada became the hottest international prospect in baseball. The Red Sox won the sweepstakes in February 2015, signing the 19-year old for a reported signing bonus of $31.5 million. With this signing, the Red Sox exceeded their bonus pool and the team had to pay 100% tax, which brought the total cost of the signing to $63 million. Also, the team was restricted from signing any international player for more than $300,000 during the next two signing periods, a move that greatly impacted the Red Sox farm system. Moncada hype was no joke as he posted never posted below a 135 wRC+ at any point in the minors. He was a September call-up in 2016 and was super aggressive at the plate, hitting .211 in a small eight-game sample. In the offseason, a “small” trade occurred and he, Michael Kopech, and Luis Alexander Basabe were off to the southside of Chicago and Chris Sale arrived in Boston. Since then, the Red Sox won the World Series and Moncada had a breakout season which led to an extension in the Windy City.
2017 - Andrew Benintendi
After playing well at the University of Arkansas, Benintendi was drafted seventh overall in 2015. He was assigned to the New York-Penn League and was promoted to Greenville after hitting .290/.408/.540 with a 175 wRC+. The Red Sox were very aggressive in promoting him and each level and he made his major league debut in August of 2016. Ever since then, he has been the everyday starter in left field and had his breakout season in 2018. He fell back down to Earth last year but he is a much better than he showed. Going forward, you can expect a player in between the 2018 and 2019 versions.
2018 - Jay Groome
Coming into the 2016 draft, Groome was thought to be the top pitching in the class but fell to the Red Sox with the twelfth overall pick due to signablilty and makeup concerns. Groome has a three-pitch mix with a fastball that sits between 92-94 MPH. However, Groome’s career has been filled with injuries and has only pitched 66 innings of baseball since 2016. He missed part of the 2017 season with an intercostal strain and forearm soreness. He started a few spring training games but was pulled from his last start. It was then reported that in May 2017, Groome had to have Tommy John Surgery. The surgery cost Groome his entire 2018 season and he did not get back on the mound until August of this past year. He needs to be added to the 40-man roster (unless MLB makes COVID-19 adjustments) or he will be eligible for the Rule 5 draft this winter.
2019 - Bobby Dalbec
Bobby Dalbec, a two-way player in college, was drafted in the fourth round of the 2016 draft. He battled a wrist injury during the 2017 season which limited him to only 85 games between the GCL and Greenville. Dalbec has great plate discipline which is key as he will have some swing and miss in his game. That being said, he cut his strikeout rate from the the high 30% to the mid 20% range while also increasing his contact% from the low 60% range to the high 70% range. Dalbec also have above average power and started to pull the ball more. We should be seeing him banging doubles off the Green Monster, if they don’t go over, very soon.