Red Sox Pitching Prospects Almost Never Pan Out

By Matt Dolloff, CBS Boston

BOSTON (CBS) — Dave Dombrowski came to Boston to run the Red Sox. Then he did Dave Dombrowski things. But amazingly, people seemed shocked.

Red Sox Twitter absolutely exploded in the wake of the news that Dombrowski had traded away highly touted pitching prospect Anderson Espinoza to the San Diego Padres for All-Star lefty Drew Pomeranz. Despite the utter disbelief of many Red Sox fans who were understandably high on the talented Espinoza, this is what Dombrowski has always done – and the unfortunate reality, here, is that the Red Sox have almost always failed to develop pitching in the past ten years, anyway.

Going back to 2006, the Red Sox have had 14 pitchers rank in the top-three prospects in the organization on SoxProspects.com. Precisely one, Jon Lester, has since reached 300 starts – or even 200.

To be fair, Jonathan Papelbon has enjoyed a strong career as a closer for the Red Sox, Phillies, and Nationals. Justin Masterson was a serviceable mid-rotation starter for about a four-year period after the Red Sox traded him to the Cleveland Indians for Victor Martinez. But other than that, it’s been one bust after another and a series of names who, at best, underachieved and failed to meet the hype.

That’s not to say that Espinoza will never pan out. He’s literally been compared to Pedro Martinez and Felix Hernandez and his stuff is eye-popping. He’s Baseball America’s No. 15 prospect as of midseason this year and is still just 18. I don’t pretend to know for sure how his career is going to go. But if Espinoza drops off between now and whenever he gets a chance to pitch in the major leagues, he would not be the first prospect to do so.

I don’t pretend to be a professional scout or have intimate knowledge of how the Red Sox develop pitchers, either. But there’s just too large of a sample size at this point to look at the results and deduce that there was a good chance the team would not have developed Espinoza properly. If Espinoza does reach his full potential, he’d be the first pitcher since Lester to emerge from the Red Sox organization as a front-line starter, and much of that development would have come from the Padres.

Here’s a brief look at every prospect in the Red Sox organization whom SoxProspects.com had ranked in their top-three at any point since the beginning of the 2006 season. Besides a few positive blips, it’s not a pretty list …

Jonathan Papelbon, No. 1 in April, 2006. Papelbon projected as a starter down the road and only temporarily as a reliever, but he stuck in the closer’s role after he thrived in it, culminating in the Red Sox’ 2007 World Series championship. “Pap” may have never reached his potential as a starter, but he has certainly been one of the game’s most reliable closers in the past decade.

Jon Lester, No. 1 in June, 2006. Lester will forever be a hero in Red Sox Nation. After a shaky start to his major league career, Lester made his presence felt with a big-time performance in the 2007 World Series and then a no-hitter in 2008. He has gone on to be one of baseball’s best big-game pitchers, including two wins and a 0.59 ERA in the 2013 World Series, and continues to pitch at a high level for the Chicago Cubs.

Craig Hansen, No. 2 in June, 2006. This is where it starts to get ugly. Hansen was the first of several flamethrowing relievers who had the potential to be the team’s closer of the future, only to flame out before ever approaching their high ceilings. The Red Sox ultimately traded Hansen, along with outfielder Brandon Moss, who has developed into a decent major league player, to the Pittsburgh Pirates as part of the Manny Ramirez-Jason Bay trade in 2008. Hansen has pitched only 6.1 major league innings since 2008 and been out of baseball since 2012.

Clay Buchholz, No. 2 in September, 2006. Remember when it was debatable whether Buchholz should have been traded for Roy Halladay? Buchholz may not be a total bust – he has shown flashes of brilliance and dominated the first half of 2013 for a team that went on to win the World Series – but he is 18-27 with a 4.82 ERA since 2013, and at age 31 probably won’t get any better from here. Buchholz has given the Red Sox some value, but the team should have cut bait years ago.

Michael Bowden, No. 2 in September, 2006. This kid, of all people, was a prospect that former Red Sox GM Theo Epstein simply refused to give up. Baseball America once projected Bowden as “a safe bet with a good chance to become a No. 3 starter.” Bowden never came close to that and hasn’t even pitched in the major leagues since he went 1-3 with a 4.30 ERA in 34 appearances for Epstein’s Cubs in 2013. Before that, he was traded for … Marlon Byrd. He actually had a great season in Triple-A in 2015, going 7-2 with a 1.91 ERA, but is currently without a team and obviously won’t reach the potential that Epstein stubbornly held onto for several years.

Justin Masterson, No. 3 in March, 2008. Masterson was dealt along with other prospects to the Indians for Victor Martinez in 2009, and looked like he was panning out in 2011 when he went 12-10 with a 3.21 ERA for Cleveland, but has dropped off significantly since then. The Red Sox brought him back on a one-year deal in 2015, but Masterson couldn’t seize a reliable role in the rotation as he went 4-2 with a 5.61 ERA in just nine starts. He signed a minor-league deal with the Pirates, but has not been able to make it back to the major leagues in 2016.

Daniel Bard, No. 3 in June, 2009. Ohhh Danny Boy. After looking on track to being a dominant reliever with an electric fastball from 2009-11, Bard and the Red Sox insisted on transitioning him to the starting rotation. That’s where things quickly went south for Bard, who hasn’t pitched in the major leagues since 2013. His most recent professional baseball experience was in 2014 with the Single-A Hickory Crawdads, a minor league affiliate of the Texas Rangers. His ERA? 175.52. That’s not a typo … his ERA was one hundred and seventy-five. Thirteen earned runs allowed in two-thirds of an inning.

Casey Kelly, No. 1 from September, 2009-September, 2010. Kelly spent a full year as the team’s No. 1 prospect and at the time was considered the real centerpiece of the 2011 Adrian Gonzalez trade, but slugging first baseman Anthony Rizzo is the only prospect in the deal who has panned out so far. Kelly is still just 26 and could further develop, but the days of him becoming a front-line starter are likely in the past. He has split time between the Atlanta Braves and their Triple-A affiliate in Gwinnett … and the Braves stink.

Anthony Ranaudo, No. 3 in April, 2011. The Red Sox traded Ranaudo to the Rangers for Robbie Ross, Jr. after a mediocre rookie season as a starter in 2014. The 26-year-old still hasn’t broken through at the major league level; in 2016 with the Rangers he had a 17.10 ERA in two appearances before being traded in May to the Chicago White Sox, where he hasn’t been able to make it to the majors from Triple-A Charlotte.

Felix Doubront, No. 3 in June, 2011. Doubront looked like a decent mid-rotation lefty starter with some upside when he pitched for the Red Sox, but has really struggled to even stay in the major leagues since the team traded him to the Cubs for infielder Marco Hernandez.

Matt Barnes, No. 2 in June, 2012. Barnes was projected as a potential top-of-the-rotation starter in 2012, when he was ranked above Xander Bogaerts and Jackie Bradley Jr., but has since emerged as merely a solid middle reliever for the Red Sox. Now 26 years old, Barnes may not completely bust out, but could have already reached his ceiling.

Allen Webster, No. 3 in June 2013. Webster barely counts as part of this list, because he came to the Red Sox from the Dodgers organization as part of the 2012 Adrian Gonzalez-Josh Beckett-Carl Crawford blockbuster, but in the interest of fairness I will include him since he was once considered a top-three prospect in the system. The Red Sox ended up trading Webster along with Rubby de la Rosa to the Arizona Diamondbacks for Wade Miley, after Webster severely struggled in the major leagues with a 6.25 ERA from 2013-14. Webster was traded to the Pirates before being designated for assignment three weeks later in December 2015, and hasn’t been back in baseball since.

Henry Owens, No. 3 in April, 2014. Owens was touted as a potential high-end starter in 2014, ranked as the No. 44 prospect in all of baseball after the season. He has not been able to overcome his control problems and, even with a Red Sox rotation in need of pitching help, can barely stick in the major leagues in 2016. Owens turns 24 years old on July 21, but the days of him having any potential beyond a back-of-the-rotation starter or middle reliever may be long gone.

Eduardo Rodriguez, No. 1 in July, 2015. E-Rod is another example of a starter that did not begin in the Red Sox organization, but the young lefty shot to the top of the organizational rankings in 2015 when he showed flashes of front-line potential. Rodriguez started the 2016 season off badly with a knee injury and has struggled compared to the expectations placed on him, but he is still just 23 years old with plenty of time to develop. The jury’s out on Rodriguez, but 2016 certainly looks like a big step backward in his development.

It’s fair to question not only the Red Sox’s ability to develop pitchers, but their ability to evaulate talent at that position in the first place. It will be a few years before we know whether Espinoza burns out or joins Randy Johnson and Johan Santana as elite starters traded away by Dombrowski.

If you truly believe Espinoza is the next Pedro, you may end up being right. Just understand that if Espinoza emerges from the Red Sox organization as that kind of top-shelf starter, he would be an outlier, like Lester turned out to be. He would not be the rule, he’d be the exception.

Espinoza may have been known as the “Red Sox’ No. 1 pitching prospect”, but in the past decade, that distinction has not necessarily been a good one.

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