Ben Cherington's complex legacy

Ben Cherington saw the best and worst of Boston sports during his 15-plus years with the Red Sox. During his tenure, Cherington oversaw multiple championships, including an improbable comeback against the 2004 Yankees. A decade later, Boston basically drove him out of town after a number of disastrous seasons, highlighted by several transactions that did not work out in the short term. Time has healed a number of these wounds, as well a quite a bit of Ben's reputation as a front-office strategist and he is back in a front office of a division rival.

Cherington started his non-playing career with the Indians in 1998 but quickly found himself part of the Red Sox organization as a video scout a year later. Boston moved him through the front office ranks, where he eventually served as Theo Epstein's deputy as the Assistant General Manager from 2009 until his promotion to the top spot with Theo's departure after the 2011 season.

Looking back at the drafts on which he collaborated with Epstein, Cherington can at least be partially credited with building the Red Sox team that is excelling today. The 2011 draft class that included the likes of Mookie Betts, Jackie Bradley, Blake Swihart, and Travis Shaw occurred on his watch, and that draft alone has already yielded nearly 30 Wins Above Replacement (per Baseball-Reference) at the Major League level.

Despite the talent acquired in the draft, Cherington took over a flailing MLB team that had the unfortunate luck of having Bobby Valentine forced upon them. It became pretty common knowledge that it was more an ownership hire than a front-office hire, and the terrible choice was at least partially rectified when Cherington recruited John Farrell back to Boston. Regardless of your thoughts on Farrell's game management style, he is no Valentine, which in and of itself has been a good thing.

2012 was a lost year at the Major League level for the Red Sox, but the season did provide Cherington the opportunity to showcase his ability to rebuild and shed payroll. That August, he orchestrated an important trade that sent Adrian Gonzalez, Carl Crawford, and Josh Beckett to Los Angeles -- a $260 million salary dump that was viewed as a victory, considering Boston was going to miss the playoffs and finish way out of first place (they came in last, 26 games back).

It was in the 2012 offseason that Cherington made his mark on the short-term eventual championship team as well as the Red Sox team we see today. The Red Sox rebuilt for the current season without sacrificing any compensation draft picks, an important point in thinking strategically about short-term versus long-term value. Cherington was integral in signing veterans such as David Ross, Jonny Gomes, Stephen Drew (yeah, he was good once), Mike Napoli, Shane Victorino, and Koji Uehara. The team finished in first place and took home the ultimate prize, defeating the Cardinals in the World Series.

Just as important as shorter-term success, Cherington's balancing act (now versus later) improved the 2014 team without signing any veterans to lengthy and expensive long term deals. In particular, Cherington passed on re-signing Jacoby Ellsbury, which proved to be a prescient move. Ellsbury was once a hugely impactful player but has been hampered by injuries and lackadaisical performance in the Bronx. Boston continues to reap the benefits of Cherington's prudence because he set the team up to promote the aforementioned Betts, Bradley, and Swihart without the drama or payroll issues caused by signing aging stars.

The results of the 2014 Red Sox looked more similar to the basement-dwelling 2012 team than the previous World Series winner, but the team still was still set up for long-term success (even if it didn't seem so at the time).

In retrospect, the biggest stumble of Cherington was not re-signing Jon Lester, who was traded for short-term value (Yoenis Cespedes) that never helped the Red Sox win himself, but did bring Rick Porcello to Boston. Whether it was ownership or the front office, the Red Sox simply did not admit the true market value of a pitcher with Lester's pedigree. That one still smarts, as Boston continues to have a tough time at the front end of the rotation.

With more knowledge of the pitching market and ownership buying in more to the cost of strong pitching, Cherington extended Rick Porcello and signed two sluggers. In Cherington's last offseason with Boston, he locked up Porcello, Hanley Ramirez, and Pablo Sandoval. At the time, the short-term value of all three signings appeared to be fairly strong; sure, the Sandoval contract probably wouldn't look great in a few years, but the present season outlook was bright. Porcello's career as a two-seam / groundball wonder would do well in Fenway, and Hanley and Sandoval would provide some much-needed pop. After the 2014 season, however, none of these signings looked smart. The Hanley left field experiment was an unmitigated disaster; Sandoval struggled with weight issues, injuries, and general malcontentedness; and Porcello threw more four-seamers than ever before, causing huge homer issues. The end was near for Cherington.

2015 again saw Boston struggle with pitching as they continually threw out Wade Miley (193 league-average innings), Porcello (25 home runs in 172 innings), Joe Kelly (ERA 22 percent worse than league average), and shortened seasons from Eduardo Rodriguez and Clay Buchholz (the best pitcher on the team that season, which surely tells you something). In August of 2015 Cherington ‘resigned,' although it was pretty obvious it was at the behest of ownership.

Oh the difference a year makes! Porcello has gone back to the two-seamer (he has allowed 21 home runs in 30 more innings than last year), and Hanley Ramirez has been an excellent part of the lineup and decent in the field. Although Pablo Sandoval still looks like a disaster contract, the team is contending.

Had Cherington stayed with the Red Sox since last August and had he been with the team today, his fingerprints on this success would be a lot more obvious. Unlike on-the-field performance, General Managers need years before reaping the fruits of their labor (Dayton Moore, anyone?), and the ups-and-downs are less attributable directly to them. Based on the successful drafting of Cherington's scouting in Boston, we can reasonably expect the Blue Jays will remain competitive now and into the future. Whether it is on-field scouting or in the front office, Ben is a scout after all, and once a scout, always a scout.

Boston has a strong GM in Dave Dombrowski, but Cherington's track record is not nearly as negative as it looked 15 months ago. Carl Triano profiled the window for the Blue Jays earlier this week, which Cherington opens wider and longer. Undoubtedly, his reputation and legacy will continue to get more complex.

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Steven Martano is an Editor at Beyond the Box Score, a Contributing Prospect Writer for the Colorado Rockies at Purple Row, and a contributing writer for The Hardball Times. You can follow him on Twitter at @SMartano.