Coolbaugh: Andrew Bailey seeking better second act in Boston as new Red Sox pitching coach taken BSJ Headquarters (Red Sox)

(Christopher Evans/MediaNews Group/Boston Herald via Getty Images)

Boston Red Sox relief pitcher Andrew Bailey signs autographs prior to a baseball game against the Oakland Athletics at Fenway Park on Wednesday, April 24, 2013.

Andrew Bailey came to Boston in 2012 with lofty expectations of replacing one of the greatest closers in Red Sox history. Those hopes never materialized over the course of two disappointing seasons that were derailed by injuries. 

Now, over a decade later, a 39-year-old Bailey is returning with a chance to finish what he started. Bailey is reportedly set to be the first major hire of new Chief Baseball Officer Craig Breslow’s tenure as the new pitching coach of the Boston Red Sox. 

Bailey’s services were apparently in high demand as Breslow’s employment offer reportedly won out over those of AL East rivals New York and Baltimore. 

Beating out the Yankees and Orioles —  a (slightly) higher profile job in New York and an up-and-coming team positioned to contend for the next few years in Baltimore — is no small feat. Kudos, Craig. A solid first act.  

One would assume Breslow had the inside track to hire Bailey given that they were teammates for parts of two seasons in Boston. (Bailey also serves as the Director of Development for Breslow’s non-profit Strike 3 Foundation charity). Both were on the 2012 roster as well as the 2013 team that won the franchise’s third of four World Series titles in 14 years. 

That is where Breslow’s and Bailey’s career arcs took a turn, though. Breslow was here for the 2013 run and pitched in the postseason and World Series. Bailey’s contributions did not extend as far as he only pitched in 30 games that season.

I remember being very excited for Bailey’s arrival. I mean, who doesn’t love a young closer on the rise? He came to Boston with a pedigree as the AL Rookie of the Year with the Oakland A’s in 2009 and two All-Star selections.

Replacing Jonathan Papelbon was no small feat, but it seemed like he would be up to the task after three solid seasons to begin his career. Alas, it wasn’t to be. He began 2012 on the disabled list following thumb surgery and lost the closer job to Joel Hanrahan (who, admittedly, I was also pretty pumped for…).

When Hanrahan got injured the following season, he reclaimed the closer role and pitched well until a shoulder injury and subsequent surgery ended his season — and his Red Sox career. All told, Bailey posted a 4-2 record, a 4.91 ERA and just 14 saves in 49 games. Nothing to write home about.

But Bailey isn’t returning to Boston to pitch — just to teach others how to do it. His time pitching in this market is a plus and could be helpful for those in-game pep talks during mound visits. A big part of being able to pitch in Boston is handling the pressure, so at least Bailey has some firsthand experience there. 

As for his resume as a pitching coach, Bailey came onto the scene in 2020 with the San Francisco Giants. The Giants finished with a sub-.500 record in the pandemic shortened '20 campaign, but bounced back in a big way the following year winning a franchise-record 107 games. 

Bailey’s pitching staff played a big role in their 2021 success. That year, Giants pitchers posted the second-best team ERA (3.24) and WHIP (1.15) in baseball. Their 524 earned runs allowed were the second-fewest in the majors, and the team’s .230 batting average against ranked fifth. 

Looking at the roster, it wasn’t as if Bailey was working with the '98 Atlanta Braves either. The Giants’ best pitcher that season was a 30-year-old Kevin Gausman, who won 14 games and struck out a career-best 227 batters. Four of the team’s five starters boasted double-digit win totals, and only one — a 35-year-old Johnny Cueto — had an ERA over 4.00. 

Gausman was the team’s lone pitching representative in that year’s All-Star Game. The bullpen wasn’t loaded with big name talent, either. Sure, plenty of credit should also be given to the team’s catcher, Buster Posey — one of the greatest backstops of his era. But their numbers across the board were impressive nonetheless and Bailey certainly deserves his share of praise.

After that, San Francisco fell off with a couple of near-.500 seasons and Bailey’s services were not retained following San Francisco’s late-season firing of old friend Gabe Kapler. Last season, the Bailey-coached Giants pitchers recorded a 4.02 ERA and 1.25 WHIP — both good for 11th best in the big leagues — and the team’s batting average against ranked 23rd at .253. 

Bailey’s successful season in 2021 after essentially only a half-year acclimation period provides hope that he can make an impact with Boston’s arms right away. But as the saying goes, you can’t make chicken salad out of chicken… well, you know.

The success of the Bailey era in Boston will come down to the pitching talent he is given to work with. A good pitching coach can help a pitcher get themselves out of a funk or reinvent their repertoire, but they are never going to be the biggest reason for a staff’s success.

If Breslow gives his former teammate some big name arms like Shohei Ohtani, Yoshinobu Yamamoto, Blake Snell, or Jordan Montgomery and the like to work with, my guess is that we’ll be saying good things about Bailey’s second act in Boston when everything is said and done. 

Gethin Coolbaugh is a contributor to Boston Sports Journal. Follow him @GethinCoolbaugh on X/Twitter.

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