Red Sox difficulties developing pitching go back twenty years

Over the last twenty years, the Red Sox have been excellent when it comes to player development at every position except for pitcher.

By and large, the Boston Red Sox have been very good at drafting and developing players. Just looking at the core of the recent 2018 World Series winners, which sported homegrown players like Mookie Betts, Jackie Bradley, Andrew Benintendi, Rafael Devers, Xander Bogaerts, and Christian Vazquez. All of these players were significant contributors and in many cases, outright stars. But what’s one thing that’s glaringly obvious about all of them?

If you answered “none of them are pitchers,” congratulations! You’re correct! Going back further (and for the sake of this article, we’re going back twenty years to 2000), the Sox have drafted and developed players like Dustin Pedroia, Jacoby Ellsbury, Nomar Garciaparra, Trot Nixon, Kevin Youkilis, and Jason Varitek. Every player listed above, save for Varitek, was drafted by the Red Sox and all them were developed in the Sox minor league system before advancing to play with the big league club.

However, when it comes to pitchers, there’s not nearly the same track record over those same twenty years. For quality pitchers (and I used the term “quality” to mean “contributed meaningfully at the major league level”), the Red Sox have developed Jon Lester, Clay Buchholz, Jonathan Papelbon, Brandon Workman, Matt Barnes, Eduardo Rodriguez, and… that’s it. All but Rodriguez were drafted by the Sox and all came through their minor league system, although Rodriguez only spent one year there.

Once again comparing the two groups, every one of those position players enjoyed or is enjoying sustained success with the Red Sox. As for the pitchers, three of them were starters and only one (Lester) has been a star; Buchholz was talented but mentally and physically fragile while the jury is still out on Rodriguez who has only successfully put it together for one entire season (2019). As for the relievers, Papelbon was at one time the best closer in the game while Barnes and Workman have been good (and at times very good) but not great.

That’s a pretty dismal track record when it comes to pitching and with twenty years to draw on, it’s a big enough sample size to say that it’s real. If we look at Red Sox pitching over the last two decades, apart from Lester, every front-line starter has been acquired either via trade or free agency. The list is incredible.

Pedro Martinez, Derek Lowe, Curt Schilling, Tim Wakefield, John Lackey, Josh Beckett, Daisuke Matsuzaka, Keith Foulke, Koji Uehara, Craig Kimbrel, Chris Sale, David Price, and Rick Porcello, not to mention the countless arms the Red Sox have used to fill out the back ends of their rotation, have all come from external sources.

The problem over the last twenty years is that the Red Sox have been so reliant on trades and free agency to fill out the pitching on their roster that now, in 2020, it’s finally bitten them hard with no relief in sight. After handing out some massive (and frankly, lousy) contracts to Sale, Nathan Eovaldi, and Price in recent years, the Sox had no money to spend on pitching heading into this season.

They now have payroll relief after the Mookie/Price trade, but it’s also the beginning of spring training and their available options are incredibly limited and not too attractive. They’ve got some intriguing pitching prospects in the minors, but most project as relievers and none are within a couple of years of truly being ready. As of the time of writing, the Red Sox rotation is Sale, Rodriguez, Eovaldi, Martin Perez, and that’s it. Given the injury history of the first two, that’s a perilously thin rotation.

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Why have the Red Sox had such a problem developing pitching for so long? Obviously there is some sort of organizational breakdown where they’re either not identifying draft picks properly or not developing them effectively in the minor leagues. Perhaps this is a Theo Epstein problem as the first decade of this wider problem was on his watch and it looks like his team since leaving the Red Sox, the Chicago Cubs, are going through the same thing.

One simple answer could be that quality starting pitching is at a premium throughout the entire league and there just aren’t enough great pitchers to go around. Those that do make it tend to be highly paid and usually do very well for themselves in free agency (looking at you, Gerrit Cole). When the Red Sox do have quality pitching prospects, they tend to either flame out before they get to the big leagues or they’re used as trade chips for other players and end up pitching well for their new teams.

Right now, a look at the top ten prospects in the Red Sox farm system (updated after the Mookie trade) shows five pitchers with two in the top five:

1. Jeter Downs, 2B/SS (No. 44 overall)
2. Triston Casas, 1B/3B (No. 77 overall)
3. Bryan Mata, RHP
4. Jay Groome, LHP
5. Gilberto Jimenez, OF
6. Bobby Dalbec, 3B
7. Jarren Duran, OF
8. Tanner Houck, RHP
9. Noah Song, RHP
10. Thaddeus Ward, RHP

However, another updated list has four pitchers listed in the top ten and only one (Mata) in the top five. Only Houck has pitched above AA and currently only Ward projects as a major league starter while the others project as relievers. Regardless of which list and ranking one goes by, the takeaway message is that the Red Sox continue to have a dearth of pitching talent in the minor leagues and that there won’t be any relief soon forthcoming.

Theo Epstein and Ben Cherington succeeded in their goals to build a “player development machine” (in Theo’s own words) and a look at the list of position players at the beginning of this article, most of whom were drafted by the duo, attests to that.

Nobody expected Dave Dombrowski to do that and he instead did what he’s done everywhere he’s been: he gutted the farm system and traded prospects for major league talent in order to win now. The four pennants and two World Series rings he’s earned across three teams is a testament to the success of his approach, but the Red Sox are now reaping the terrible cost of what he sowed.

It will now be up to Chaim Bloom to reverse two decades of Red Sox futility and hopefully restock the minor leagues with quality pitching prospects who will one day blossom into major league starting and relief pitchers. It was more than a little shocking that none of the players he received in return for Mookie and Price were pitchers, but it will be more fair to circle back in a couple of years to see if he’s replenished the farm with pitchers.

As with any team in any season, the Red Sox will only go as far as their pitching and right now with a thin rotation led by two highly paid injury-prone starters, a mishmash of a bullpen, and no talent on the horizon coming from the minor leagues, it looks like the 2020 Red Sox probably won’t go too far.