Overview
We all know the Red Sox haven’t developed a single viable starting pitcher (i.e., one who gave the team 100 starts) since Clay Bucholz. In fact, between 2007 and 2022 the most starts for Boston by a pitcher signed and developed by the organization was…69, by Felix Doubront (2010, 2012-2014). In that fifteen-year period the Red Sox not only failed to provide themselves with a homegrown starter but even the ones they traded away generally failed to make a major league impact (Justin Masterson is the sole exception with 184 career starts, or about two and a half Doubronts). The following is a full list of every pitcher ranked as one of the Red Sox ten best prospects since the debut of Clay Bucholz (as measured by soxprospects.com), what happened to them, and if possible, why they did not make an impact at the major league level.
Note: For the sake of my sanity and yours I did not include any pitcher who failed to make multiple appearances on one of the three rankings done by soxprospects.com in consecutive seasons. In practice this means I will not acknowledge the guy who was ranked eighth in June 2017 because he had a good month at Single A. Hardcore Travis Lankins fans and Trey Ball-truthers may feel free to politely vent their frustration. I am also not including guys still in the organization.
Justin Masterson (2006-2008)
Masterson is both the last and first of his kind, a genuine starting pitcher prospect who succeeded in the bigs as well as a disappointment for the Sox. A mid-season callup in 2008, Masterson worked as both a fill-in starter that year as well as an excellent middle reliever, posting a 3.16 ERA in 36 games (nine of which were starts)/ nearly 90 innings; Sox Prospects predicted his ceiling as “a #3starter or a dominant set-up man,” depending on how his ability to control his sinker developed. Through the first half of 2009, this dual role for Masterson continued until he was traded to Cleveland as part of the package for Victor Martinez. The Indians committed to Masterson as a starter and by 2011 he was their de facto ace (this was right before they came up with Kluber and Carrasco and the rest of those mid to late 2010s staffs); between that season and the next two Masterson became an archetypal mid-rotation workhorse, pitching 615 innings with a 3.86 ERA (100 ERA+). However, in his walk year he suffered a series of injuries to his knee, back, and shoulder, was traded to the Cardinals at the deadline, and struggled with control throughout en route to a career worst 5.88 ERA. That winter the Red Sox brought Masterson back on a one-year prove it deal, but the lingering effects of those ailments had essentially ended his career; after being released that August Masterson never again pitched in the majors. Overall, he had almost exactly half the career of fellow burly righthanded sinker baller Derek Lowe.
Michael Bowden (2008-2009)
Bowden was the first prospect I followed who failed to make a major league impact, and thus has come to be the face of this era of flopped arms in my mind’s eye. In hindsight, his status as the top starting pitcher prospect in the Red Sox organization was probably inflated by the preceding graduations of Papelbon through Masterson and his pedigree as a first round pick in 2005; Bowden had four average pitches but no exceptional offerings, which allowed him to quickly reach AAA before stalling out as an apparent Quad-A talent. The Sox swapped him to relief after brief cups of coffee in 2009 and 2010 but he never progressed further. Bowden saw most of his big-league career as a low-leverage reliever for the 2012 and 2013 Cubs, totaling 75 replacement level innings. After that he never appeared in a major league game, though he was still playing independent ball as late as 2021.
Nick Hagadone (2008-2009)
Hagadone was another part of the Victor Martinez package, though he did not come nearly as close as Masterson to fulfilling his headlining role in that deal. Only recently returned from Tommy John at the time of the trade, the 2007 first rounder struggled to progress as a starter and (like Bowden) converted into a low leverage reliever. Unlike Bowden, Hagadone did not even provide replacement level production, bouncing between Cleveland to Triple A Columbus for several years before being nontendered in 2015.
Junichi Tazawa (2009*)
Sox fans will best remember Tazawa for his role as Uehara’s set up man in 2013, but he had originally been signed by the Red Sox as a starter in December 2008. Injuries and ineffectiveness had forced the move to the bullpen before 2012, but this of course was more than a mere salvage attempt—Tazawa was one of the better relievers in baseball for the next four seasons, appearing in 240 games with an even 3.00 ERA and even more lights-out peripherals (9.1 K/9 against a mere 1.8 BB/9). He lost his effectiveness by the second half of 2015, but it seems safe to say that Tazawa represents the upper echelon of Red Sox pitching prospects since 2007.
Casey Kelly (2008-2010)
Kelly was actually drafted in the first round as a two-way player in 2008, but after about a season and a half of terrible hitting at the lowest levels, the Sox agreed to Kelly’s preference to be a full-time pitcher. A rocky 2010 debut at Single A did not deter the Padres from making him half the headlining return for Adrian Gonzalez before the 2011 season (the other half being Anthony Rizzo). Kelly dominated AA ball that year, and had reached the majors by late 2012, winning his first start with six shutout innings against the Braves. However, from there it was all downhill, as he struggled through September, tore his UCL the next spring, made an abbreviated return in 2014 before injuries once again wiped out the rest of his season, and tried switching to relief in order reduce the strain on his arm. While ostensibly healthier, Kelly struggled mightily in the upper minors and began bouncing from organization to organization before his professional career in America ended in 2018. Since then, he’s been one of the best starters in the Korean baseball league, so he may yet have a Ryan Vogelsong-esque twist to his career.
Stolmy Pimentel (2009-2011)
Despite his fantastic name, was never more than your typical intriguing arm signed out of the DR as a teenager. Sox Prospects gave his ceiling as either a back of the rotation starter or decent late reliever; as it was, Pimentel never gained more than a series of brief appearances on a major league roster (primarily for the 2013 and 2014 Pirates). His most worthwhile contribution for the Red Sox came when he was traded to Pittsburgh (alongside Mark Melancon and two throw ins) for all-star closer Joel Hanrahan and some light-hitting middle infielder named Brock Holt.
Anthony Ranaudo (2010-2014)
Ranaudo is yet another first round pick who failed to make it, but unlike Bowden and Hagadone he was highly regarded across baseball as a top prospect. Having fallen to the 39th overall pick due to concerns over an elbow injury in college, he steadily worked his way to majors despite a lost 2012 season, debuting with seven starts in the last two months of the 2014 season. Unfortunately, that’s as good as it got for Ranaudo as despite excellent numbers in the minors he failed to impress at the big league level and was swapped to the Rangers that winter for Robbie Ross. A mediocre 2015 at Triple A wiped off more of his former luster and after spending most of 2016 in the White Sox organization Ranaudo was done in American pro ball. Like Kelly, he tried salvaging his career in Korea; unlike Kelly he flunked out after a single season, which did indeed mark the end of his professional pitching career. Ranaudo never developed a viable third offering to complement his fastball and curve, and this likely was the largest factor in his failure to fulfill the hype.
Felix Doubront (2010-2011)
Between Masterson and Houck, Doubront is the closest the Red Sox have come to developing a starting pitcher for themselves. Signed as sixteen-year-old in 2004, Doubront slowly worked his way up the major league level, usually repeating each course along the way. Promoted several times through the second half of 2010, he made a generally favorable impression, though issues with command prompted questions of making him a reliever. A poor 2011 at Triple A brought up concerns about both his work ethic and long-term prospects. Nonetheless, when injuries and ineffectiveness forced the Red Sox to turn to Doubront as a rotation mainstay in 2012 the Venezuelan southpaw stood strong and mostly met the challenge, providing 161 innings of average pitching. He would do much the same in the miracle year of 2013, but in neither season was he more than an acceptable fourth starter. When the wheels fell off in 2014 so did Doubront’s career; he was traded to the Cubs at the deadline for a player to be named later (later to be named Marco Hernandez). Since his control was never more than poor, Doubront’s career could not long survive a K/9 below 8. He appeared in his last major league game in 2015 at the age of 27.
Matt Barnes (2011-2015)
Part of that legendary 2011 Red Sox draft class, Barnes featured a classic fastball/curveball combination. Injuries, inconsistency, and the failure to add a third pitch equal to those first two led to a conversion to relief, though in this case he has more in common with Tazawa than Bowden and Hagadone. Barnes had three solid seasons then made the all-star team in 2021 as a closer, which earned him a three-year extension. Unfortunately, long-standing confidence issues and (again) injury led to a fall as swift as his rise; Barnes pitched poorly after the break and through 2022 before being dumped on the Marlins in a swap of fading relievers. Right now, he’s working out of Washington’s bullpen.
Henry Owens (2012-2015)
Like Matt Barnes, Henry Owens was drafted by the Sox in 2011. Unlike Barnes, Owens stayed a starter throughout his professional career. He tore through the minor leagues, reaching AAA by the time he was old enough to drink, en route to an extended major league audition in 2015. At first glance, Owens did not pitch too poorly—his peripherals were average, as were his results (4.57 ERA in sixty-three innings). But the Red Sox (now under Dave Dombrowski) were unimpressed with his stuff and sent him back to AAA for 2016, where he again did well. In five starts in the majors that year Owens was admittedly smacked around, but given his track record up until that point you could still envision him earning at least a back of the rotation spot if granted the opportunity. Unfortunately, he started struggling with command, getting sent all the way back to AA ball, was waived to Arizona and then the Dodgers in a matter of weeks. Owens pitched in only five more professional games before spending a final few years in independent ball.
Until doing research for this post, I would have thought of Owens in the same class as Ranaudo or Bowden; now I think of him as being closer to Blake Swihart—a former first round pick from 2011 who worked his way to the majors by 2015, did well in his rookie year, then was dislodged by the new regime, his apparent faults exaggerated in order to explain why he was being shafted. Look, if Owens was ever going to become a major league pitcher, it was not going to happen in AAA, just as Swihart was never going to become a better catcher by breaking his ankle in the outfield. The fourth and fifth starters for the Red Sox in 2016 were Clay Bucholz and Drew Pomeranz; Owens’ 2015 was just as good if not better than what those two “provided” and he was considerably cheaper, too.
Allen Webster (2012-2014)
Webster came to the Red Sox organization through that August 2012 megadeal with the Dodgers that sent Adrian Gonzalez, Josh Beckett, Carl Crawford and Nick Punto west. That trade was primarily a salary dump, but Webster (with fellow pitching prospect Rubby de la Rosa) had some potential. Of course, he never actually fulfilled this potential; if Owens was the guy with results better than his stuff, then Webster was the guy who’s stuff was better than his unexceptional results. He crested with a couple of decent years at AAA, bombed in abbreviated big league action, and ended his career in Cubs organization…for those keeping count, that’s the fourth failed Red Sox pitching prospect later acquired by the Theo/Hoyer Cubs (Bowden, Kelly, and Doubront being the other three). Webster and Owens also had stints in Mike Hazen’s Diamondbacks.
Brandon Workman (2013-2014)
Also known as “Matt Barnes at home,” Workman was a college righthander with a good fastball/curveball combination who never developed a viable third pitch and wound up in the bullpen as a result (2015 Tommy John surgery didn’t help). Workman only had one good season out of the ‘pen, which you probably remember Chaim Bloom was somehow able to spin into Nick Pivetta. What you may not remember is that Workman was released by the Phillies after 2020 only to be signed by the Cubs—that’s right, he’s the fifth Theo/Hoyer expat.
Brian Johnson (2014-2016)
Brian Johnson had one of the unluckiest careers of any pitcher mentioned here. A big southpaw drafted out of Florida in 2012’s first round, Johnson had the solid repertoire of the stereotypical crafty lefty starter. Unfortunately, his professional career was one freak mishap after another—a line drive to the face during the 2012 Futures’ game in Fenway meant he couldn’t eat solid food for months, let alone keep in shape, which led to a shoulder injury at the start of 2013. When he was finally healthy, Johnson cut a swath through minor league hitting, most notably a 1.75 ERA in 118 innings at AA which was followed by 2.53 ERA the next year at AAA and his major league debut…whereupon an elbow injury ended his season early. Latent anxiety issues then started plaguing Johnson, even threatening to end his career at one point. He came back, of course, and will be best remembered as the swingman for the greatest team in Red Sox franchise history.
Michael Kopech (2015-2016)
Kopech shouldn’t actually be listed here due to my criteria, but he deserves a mention as part of the trio of prospects that brought Chris Sale to Boston. With a peak velocity of 102mph, Kopech’s heater could only ever be matched by his personality—in his first pro season, he was suspended fifty games for using a banned substance. Ok, that stuff happens, maybe he really did just accidentally take a tainted supplement as he claimed—and then the next March he broke his hand punching his roommate. Kopech’s turbulent off-field life has followed him to the big-league level: in January 2020, Kopech married Canadian actress Vanessa Morgan; in June 2020 Kopech filed for divorce, a month after the announcement that the couple were expecting their first child.
Kopech is currently the White Sox closer.
Jay Groome (2016-2022)
Groome is the classic “There’s No Such Thing As A Pitching Prospect,” a first rounder who has never come close to fulfilling his selection spot due mostly to injuries. He had his first full professional season last year, making 30 starts at Triple A; he also posted a 8.55 ERA and walked seven and a half batters per nine innings.
Jalen Beeks (2017-2018)
Beeks, like Kopech, would not be here if not for his inclusion in a major trade—in this case the deal that brought Nate Eovladi over from Tampa in 2018. One of few pitchers who did not become a Cy Young Award contender immediately after putting on a Rays uniform, Beeks has been an unexceptional swingman after parts of six seasons. He started 2024 as a Rockie reliever, which is not unlike being the understudy for an extra in a high school play.
Darwinzon Hernandez (2017-2018)
Finally, we have Darwinzon Hernandez, the wild lefty reliever. Darwinzon has never walked less than four men per nine and he’s not likely to stop anytime soon. Seventy low leverage innings between the 2019 and 2021 seasons seem likely to be the extent of his major league career, as he is now a member of the f*ckuoka SoftBank Hawks. In his sole appearance last year he faced seven batters, hitting one, walking one, striking out one, and allowing two earned runs. Bless ‘im—all the way on the other side of the world and he hasn’t changed one bit!
Conclusion
Looking back at the past fifteen years of disappointment, four distinct types of failed pitching prospects come clear:
The Reliever: Matt Barnes and Junichi Tazawa are obviously the best of this group, though you can also include Brandon Workman, Michael Kopech, and Darwinzon Hernandez. These guys had good fastballs and maybe an equal second offering but never found that third pitch that would make them a starting pitcher. Injury presumably made the decision to convert to full time relief easier.
The Never-That-Good: These pitchers were the beneficiaries of either a weak system, overhype, or both. Michael Bowden is the forefather, followed by Nick Hagadone, Stolmy Pimentel, and Allen Webster.
The Injury-Derailed: Casey Kelly is the clearest example, but Brian Johnson’s numbers until his 2015 MLB debut clearly reflect a higher ceiling than he reached. Jay Groome also belongs here, the sole pitcher to have never made an appearance in the big leagues.
The Deserved Better: Henry Owens, literal and spiritual batterymate to Blake Swihart.
This leaves Felix Doubront and Anthony Ranaudo as apparent exceptions, though you could place the former in the “Never-That-Good” category given his high ranking was due at least in part to coming along directly after the Papelbon-Masterson generation graduated. Ranaudo’s failure to become even a back of the rotation option is, to my understanding, nigh inexplicable even in hindsight.
If I had to hazard an educated guess on the future categorization of current Red Sox “pitching” prospects, I would place Mata in the Reliever group, Noah Song next to Jay Groome in Injury-Derailed. Dick Fitts, Winkelman Gonzalez, and Luis Perales all deserve more time to prove themselves before even conjecturing their projections.
