This is the first of two pieces on the Pirates’ new GM. I’ll take a look here at the Red Sox’ fortunes in the majors under Ben Cherington. The next one will cover the Sox’ and Blue Jays’ farm systems during his time with those teams.
The Sox’ situation when Cherington took over as GM after the 2011 season was similar to the Pirates’ current situation in some ways, and very different in others. Boston in 2011 had won 90 games, but fell out of first in a late-season collapse. Veteran manager Terry Francona departed and team suffered a lot of internal dissension. Much of the latter centered on a bizarre clubhouse scandal involving fried chicken, beer and video games, as well as bickering over the source of the story. Unlike the Pirates, the Sox were a veteran team mostly populated by long-established players.
With a mostly set roster, Cherington didn’t have a great deal to do after taking over from Theo Epstein in October. Closer Jonathan Papelbon left as a free agent a few days after Cherington took over and Cherington did not replace him successfully. He added Mark Melancon in a trade for Jed Lowrie, but Melancon had a terrible season, much to the Pirates’ later benefit. Cherington made one minor free agent signing, outfielder Cody Ross, who had a strong season for a cost of $3M.
Cherington’s first team fell to 93 losses and a last place finish. It’s hard to fault Cherington much for this, as he was pretty much stuck with a veteran team and some bad Epstein contracts. Adrian Gonzalez, Jacoby Ellsbury, Jon Lester, and Clay Buchholz dropped off sharply; Josh Beckett and Kevin Youkilis collapsed; setup man Daniel Bard’s career largely ended due to injury and wildness; David Ortiz missed nearly half the year; and Daisuke Matsuzaka tried unsuccessfully to return from injury. In August, though, Cherington achieved the mother of all salary dumps, unloading zillions of dollars worth of Carl Crawford, Beckett and Gonzalez on the Dodgers for some random guys.
In the offseason, Cherington retooled the Sox for relatively modest cost, in big-market terms. He signed Mike Napoli (1/$13M), Stephen Drew (1/9.5), Jonny Gomes (2/10), Shane Victorino (3/39), Ryan Dempster (1/13.25) and Koji Uehara (2/9.25) as free agents, and all had good years (spectacular in Uehara’s case). He also good a good year from Mike Carp, whom he acquired for cash. His most significant trade sent Mark Melancon and some guys to the Pirates for Joel Hanrahan and Brock Holt. Hanrahan’s career quickly went south due to injury, but Holt eventually salvaged the deal for the Sox. In the rule 5 draft, the Red Sox lost Josh Fields and Ryan Pressly, both of whom eventually became productive relievers. Cherington made one meaningful deadline trade, getting Jake Peavy in a large, three-team trade in which the Sox gave up Jose Iglesias. Peavy was just decent in his time in Boston. Beyond all that, a number of the veterans bounced back and/or stayed healthy, and the Sox won 97 games and the World Series.
During the next offseason, Cherington didn’t make a lot of changes. One reason apparently was the emergence of some promising rookies from the Sox’ rapidly improving farm system. He resigned Napoli (3/45), a move that worked out poorly. He also signed A.J. Pierzynski (1/8.25), a move that went so badly that Cherington released Pierzynski during the season. The Sox also signed reliever Edward Mujica (2/9.5), who had a decent season. The Sox gave regular jobs to Xander Bogaerts and Jackie Bradley, Jr., both of whom struggled. Mookie Betts came up at mid-season and hit the ground running. Meanwhile, nearly every veteran position player, even Pedroia, fell off, as did Buchholz. Second year third baseman Will Middlebrooks collapsed and an attempt to resurrect Grady Sizemore’s career failed. In June, Cherington re-signed Drew, who hadn’t been able to get a deal he liked, for $10.1M and Drew was terrible. The Sox couldn’t score runs and finished last, losing 91 games.
With the team out of it at the 2014 deadline, Cherington traded walk-year pitchers Jon Lester and John Lackey, not for prospects, but for major leaguers Yoenis Cespedes, Allen Craig and Joe Kelly. Craig quickly played his way out of baseball, Cespedes departed the next offseason in a trade, and Kelly eventually became a good reliever after trying to make it as a starter for about two years. Cherington also traded two months of Andrew Miller for a prospect, Eduardo Rodriguez, who’s now a rotation mainstay for Boston. In August, Cherington disastrously signed Cuban Rusney Castillo to a $70M major league contract.
During the off-season, Cherington made his two really big (again, but large market standards) free agent signings, and they didn’t go well. Hanley Ramirez (4/88) and Pablo Sandoval (6/95) both bombed. Cherington also traded Cespedes, who was a year from free agency, for Rick Porcello, who’s been an innings-eater for the Sox except for one big, Cy Young season. Cherington also picked up Wade Miley for some random guys. Miley had a solid 2015 season for Boston.
Boston’s 2015 was sunk by bad contracts, but some important progress was obvious. Napoli, Sandoval, Ramirez and Castillo were all terrible. The team got good production, though, from Betts and Bogaerts, and Bradley, rookie infielder Travis Shaw and rookie catcher Blake Swihart all had productive half-seasons. The weighted average age of the team’s hitters, which had been an older-than-league-average 29.1 to 29.6 the previous three years, dropped to a younger-than-average 28.2 despite the 39-year-old presence of David Ortiz. The Sox were 14 games under .500 through July 29, but were eight games over the rest of the way. They finished last, but went 78-84. Cherington resigned as GM after Boston brought in Dave Dombrowski to oversee him.
It’s obviously hard to draw any conclusions about Cherington’s likely actions with the Pirates when you look at his Boston tenure. He inherited a roster loaded with established veterans; the team had won 90+ games in eight of the previous ten seasons. The farm system hadn’t quite started to produce yet, so significant changes weren’t going to happen. It was also a group of veterans who tended to have some highly variable performances. And, of course, Cherington won’t have anything remotely like the budget he had. He’ll be lucky to be able to afford Pablo Sandoval’s gardener, much less Sandoval himself. The disastrous signings, most of which occurred in late 2014, can’t happen in Pittsburgh.
Another reason it’s hard to draw conclusions from those Boston years is that the game has changed rapidly in the few years since then. (I swear I wrote this before Cherington said in his press conference that player development practices have changed dramatically in the last few years.) We’ll have to assume for now that Cherington is aware of trends in the game, something that can’t be said of Neal Huntington in his last several years. It’s also important to take into account the environment in Boston, where the expectation was to aim for the World Series every year, regardless of the team’s overall situation. I think it’s fair to say that Cherington had at least as much to do with the Sox’ success from 2016-18 as did Dombrowski, but the pressures in Boston are such that he wasn’t around to benefit from the groundwork he laid.
Cherington’s tendency in the free agent market was to go after second-tier, rather than premier, players. This led him to players with histories of injury, poor conditioning and/or erratic performance. It worked well when he gave out one-year deals, like with Napoli and Drew the first time around, but not with longer deals. In the last few years, teams have virtually stopped giving out contracts like the ones Cherington gave to Napoli the second time, or to Ramirez and Sandoval, recognizing them as high-risk and inefficient.
Another, related difference is that teams, or at least the best-run ones like the Astros and Dodgers, are ferociously determined to hoard high-performing, 0-6 players. That’s the best insurance against getting mired in commitments to weak or erratic veteran performers, which plagued the Sox during Cherington’s tenure. He’s going to have to aim for that sort of roster with the Pirates because he’s barely going to be able to afford any veterans. Presumably, that would also lead him, when he trades veterans, to look for prospects rather than players like Cespedes (who had only a year and two months before free agency) and Craig, who just wasn’t any good. Cherington obviously was willing to give jobs to players like Betts, Bogaerts and Bradley when they were ready, which isn’t always easy to do in a big market like Boston.
One last subject — Cherington tended to build bullpens with a variety of veterans, generally without spending big money. He didn’t have great success at it. In his four years, the Sox’ bullpen was 11th, 10th, 6th and 13th in the AL in ERA, albeit in a high-scoring environment at Fenway and in the AL East. He did come up with a great closer for a couple years in Uehara, at modest cost.
SONG OF THE DAY
DAILY QUIZ
TODAY IN PIRATES HISTORY
By John Dreker
Eight former Pittsburgh Pirates born on this date, plus one major trade of note.
On this date in 1962 the Pittsburgh Pirates traded star shortstop Dick Groat and pitcher Diomedes Olivo to the St Louis Cardinals for pitcher Don Cardwell and infielder Julio Gotay. The traded basically ended up being Groat for Cardwell, since neither Olivo or Gotay played much for their new team. Groat had two big seasons in St Louis before his stats started falling off. He finished second in the 1963 NL MVP voting and was an All-Star in 1964. Cardwell spent four years in Pittsburgh, posting a 33-33 3.38 record in 84 starts and 22 relief appearances. His best season was 1965 when he went 13-10 3.18 with 240 innings pitched.
John “Denny” Driscoll, pitcher for the 1882-83 Alleghenys. He went 13-9 that season in 23 starts and lead the AA in ERA with a 1.21 mark in 1882, then had an 18-21 record in 1883. The team went 13-46 in games he didn’t pitch.
Billy Sunday, outfielder for the 1888-90 Alleghenys. Considered to be the fastest base runner of his era, he was a .243 hitter in 287 games with Pittsburgh. Sunday stole 174 bases during that time. He retired after the 1890 season to become an extremely famous evangelist.
Billy Zitzmann, outfielder for 1919 Pirates. Hit .192 in 11 games before being sold to Reds in June of 1919. Played six years in Cincinnati, though he was in minors from 1920-24.
Elmer Tutwiler, pitcher for 1928 Pirates. Tutwiler’s entire big league career consisted of two late season appearances for the 1928 Pirates. He threw a total of 3.2 innings, allowing two runs.
Stu Martin, infielder for the 1941-42 Pirates. Hit .305 over 88 games during the 1941 season, then dropped down to .225 in 1942. Hit .268 in 722 games over eight years, spent also with Cardinals and Cubs.
Manny Jimenez, pinch-hitter/left fielder for 1967-68 Pirates. He was traded to the Cubs in 1969 in three player deal. Jimenez hit .279 in 116 games with Pirates. During the 1968 season, he batted .303 and had 66 at-bats in 66 games. He started just nine games in his two seasons in Pittsburgh. Jimenez had just six major league at-bats after leaving Pittsburgh. He played a total of seven seasons in the majors, hitting .272 in 429 games. In ten minor league seasons, he batted .311 in 818 games. During his rookie season in 1962 with the Kansas City Athletics, Jimenez hit .301 with 69 RBIs in 139 games, all three stats were career highs. His brother Elvio Jimenez played one game in the majors, getting six at-bats for the New York Yankees on October 4, 1964.
Bobby Tolan, first baseman for 1977 Pirates. Was originally signed out of high school by Pittsburgh in 1963, but didn’t play for the team until 14 years later. Tolan hit .203 in 49 games for Pirates after being signed as a free agent mid-season. He played 13 years in the majors, spending time with five different NL teams.
Jonathan Sanchez, pitcher for the 2013 Pirates. Went 0-3, 11.85 in four starts and one relief outing before being released. He won 38 games over eight seasons in the majors, including 13 games for the 2010 World Series winning San Francisco Giants.
