A couple of weeks ago, I was poking around Sox Prospects, as one does. The catalyst for this, if I am remembering correctly, was to look at how Aníbal Sánchez ranked among Red Sox prospects before he was traded. This post is not about that, though. As I was moving around the site, I found a page I don’t believe I had ever seen before: A list of unsigned Red Sox draftees. Anyone who follows the draft knows unsigned picks are not at all uncommon, and it is just how the process works. High school players who are not taken early are typically very likely to opt for college instead of signing for a relatively low signing bonus. As such, there are a players every year who go unsigned but end up becoming great players. The Red Sox are no exception here. With that in mind, I decided it would be fun to create a lineup of the best players who the Red Sox have drafted over the years that did not end up signing. Note that these date back to 2003.
The Red Sox drafted Yasmani Grandal out of Miami Springs High School in the 27th round back in 2007. The catcher was committed to the University of Miami and decided to forgo signing with the Red Sox and instead went to play for The U. He was later drafted in the first round by the Reds in 2010. He ended up being a consensus top-100 prospect heading into the 2012 season, and has since turned into one of the best catchers in baseball. Grandal regularly ranks among the top pitch framers behind the plate and has developed into a very good hitter as well. The two-time All-Star has never had a major-league season with a below-average OPS+.
Belt was actually a realistic signee, as he was drafted in the 11th round in 2006 out of Hudson High School in Texas. That is the round in which teams often use money saved in the first ten rounds to sign a high-upside high school player. Belt decided to attend the University of Texas, though, and turned himself into a fifth round pick by the Giants in 2009. The first baseman ended up as a top-25 prospect in baseball by both Baseball America and Baseball Prospectus prior to the 2011 season and has turned into a very solid player for San Francisco. Playing in the hitter’s hell out there hasn’t helped his raw numbers, but he has been an above-average hitter after adjusting for park effects in every season besides this past one. Over his first five full seasons in the majors, he posted a 130 OPS+ and he earned himself his lone All-Star bid in 2016.
I’m taking some liberty here in the positioning, but I’m the manager so who’s going to argue with me?! Shaw was a 32nd round pick in 2008 by the Red Sox out of Washington Senior High School in Ohio. He ended up going to Kent State instead of signing with Boston, but of course ended up in the organization anyway. Shaw was drafted again by the Red Sox in 2011, this time in the ninth round. He worked his way up through the system and eventually broke through into the majors in 2015. After a strong showing that year and a decent time in a bigger role in 2016, he was traded to Milwaukee as part of the package that brought Tyler Thornburg to the Red Sox. He, of course, thrived with the Brewers for his first two years before having a disastrous 2019.
This is easily the worst position here, no disrespect to Mr. Riddle. The shortstop was taken by the Red Sox in the 35th round back in 2010 out of Western Hills High School in Kentucky but decided to attend the University of Kentucky instead. A few years later he would be drafted in the 13th round by the Marlins and signed with them. Riddle ended up making his major-league debut in 2017 and has been a defense-first depth option since then. Over three partial seasons he has posted a 73 OPS+ but has still been above replacement level due to his defense.
And we go from the worst player on the team to the best one. This one shouldn’t be much of a surprise to see as Bregman was mentioned as a former Red Sox draftee approximately 828 times during last year’s ALCS. The potential 2019 AL MVP was taken as a second baseman by Boston in the 29th round in 2012 out of Albuquerque Academy in New Mexico. He ended up deciding to attend LSU instead, which was a good call on his part as he ended up being the second overall pick by the Astros in 2015. Since then, all he’s done is turn himself into one of the biggest stars in the game and the best player on perhaps baseball’s best team. Bregman is a phenomenal defensive third baseman who can also play shortstop if need be while coming in as the fourth best hitter in baseball by OPS+ since the start of 2018. He trails only Mike Trout, Christian Yelich and Mookie Betts in that regard.
Renfroe is a corner outfielder now (he plays more right field than left field, but again I’m taking liberties) but he was actually drafted as a catcher by the Red Sox. That was back in 2010 when they took him with their 31st round pick out of Copiah High School in Mississippi. He’d go on to attend Mississippi State and was later drafted with the 13th overall pick by the Padres in 2013. The now-outfielder was a consensus top-100 prospect for three years and a four-time top-100 prospect on Baseball America’s list. He hasn’t exactly turned into a start for the Padres, but he is a solid defender and has big enough power to overcome some of the other flaws at the plate.
Bregman is the clear star on this team, but Blackmon comes in as a clear number two in this lineup. Like Renfroe, Blackmon wasn’t taken as an outfielder from high school. Instead, the Red Sox drafted the Rockies star as a pitcher out of Young Harris College in Georgia before transferring to Georgia Tech instead of going to the Red Sox. He was a 20th round selection in 2005 for Boston and ended up being selected in the second round in 2008 by the Rockies. He was never a top prospect, but he’s emerged as a legitimate star in Colorado. Blackmon has made four All-Star teams, received MVP votes twice and won two Silver Sluggers in his career so far. Now getting into his mid-30s he’s not the athlete he once was, but in his prime he patrolled center field while combining batting average, power and speed offensively.
Of course I had to include the younger Yaz here. The grandson of the franchise icon was taken by the Red Sox out of St. John’s High School in Shrewsbury in the 36th round of the 2009 draft. Yastrzemski opted for college instead of signing, going to Vanderbilt. He was drafted in the 30th round by the Mariners in 2012 but went back for his senior year before being selected in the 14th round by the Orioles the following year. He spent six years in Baltimore’s system before being traded to the Giants before the 2019 season. He of course was promoted this past year and performed very well, putting up a 123 OPS+ in 107 games.
I was actually a little surprised the Red Sox didn’t fail to sign any names bigger than this from the starting pitcher pool, though I suppose this speaks to both the difficulties in identifying and developing starters as well as Boston’s specific struggles in this regard. Desclafani is not a terrible name, though, and at one point looked like one of the better young arms in the game. Boston took him in the 22nd round of the 2008 draft out of Colts Neck High School in New Jersey but he decided to go to the University of Florida. He was later selected by the Blue Jays in the sixth round of the 2011 draft. He was later traded to Miami as part of a massive deal that brought Mark Buehrle and Jose Reyes, among others, to Toronto. He’d go to the Reds in 2014 and he had an outstanding 2016 before injuries derailed his career.
We end with a fun one given the rumors surrounding the Red Sox and the Padres closer throughout last season. Obviously it never came to fruition, but it made sense given Boston’s perceived needs and Yates’ immense talent. He was taken in the 26th round by the Red Sox back in 2005 out of Kauai High School in Hawaii before going to junior college. He was never actually drafted again, but was signed as an undrafted free agent by the Rays in 2009. After that he bounced all around the league for a while before landing with San Diego in 2017. Since then, he’s emerged as one of the top relievers in all of baseball.