Coincidentally, Tuesday marked the second time in 11 years that Andrew Bailey has left the Bay Area to join the Red Sox. He’s hopeful his re-introduction to Boston will go smoother than his initial stint with the organization more than a decade ago.
Long before launching a coaching career that would land him in Boston as Alex Cora’s pitching coach, Bailey was one of baseball’s best young relievers who was traded from the Athletics to the Red Sox in a significant offseason trade. In Dec. 2011, Oakland shipped Bailey, a 27-year-old two-time All-Star closer, to the Red Sox along with outfielder Ryan Sweeney for outfielder Josh Reddick and prospects Miles Head and Raul Alcantara.
Bailey’s playing tenure in Boston included being part of a World Series championship in 2013 but was largely lost to injury. Due to a thumb injury that cost him the first 4 ½ months of 2012 and shoulder surgery that cost him the second half of 2013, Bailey was limited to just 44 total innings in a Red Sox uniform. Acquired to be a dominant closer after the departure of Jonathan Papelbon, Bailey saved just 14 games for Boston over two seasons before departing in free agency. Reddick went on to be a solid contributor for the A’s for a half-decade.
For Bailey, returning to the Red Sox after four seasons as San Francisco’s pitching coach represents more than just a chance to be closer to his family’s Connecticut home. It’s also a full-circle moment.
“I’m selfishly really excited for this opportunity,” Bailey said Tuesday. “I have always found Boston to be a special place to play as a visitor and as a former Red Sox player being a part of a championship team. But I think selfishly, I know I was brought there to do a job and unfortunately, as a player, I wasn’t able to do that job to the best of my ability due to injuries. It’s not too frequent you get a second opportunity to right the ship in a different capacity. So I’m excited, I’m motivated. I’m ecstatic about the opportunity because I know it doesn’t come around that often.”
Bailey missed the entire 2014 season after undergoing surgery to replace labrum and capsule damage in his throwing shoulder and pitched just 59 more games for the Yankees, Phillies and Angels before retiring in 2017 at age 33. He immediately jumped into coaching in 2018 with the Angels, remaining with the organization as and instant replay coordinator and coaching assistant before becoming bullpen coach in 2019. A year later, he moved north as Gabe Kapler’s pitching coach and served that role for the Giants for the last four years.
The New Jersey native has, like his new boss and close friend Craig Breslow, long kept a home in Connecticut. He entered the 2023 season knowing that his preference would be to return to the East Coast once his contract expired in San Francisco.
Bailey, who has three children under 13, said coaching two hours from home represented the best opportunity for him at this juncture of his career. Even before Breslow was hired, Bailey said, he reached out to Sox executive Brian O’Halloran and others in the organization to express his interest in replacing Dave Bush at the helm of Boston’s staff.
“I want to be the best husband, best dad and work in baseball. Those are the three things I love in life,” Bailey said. “I was at the point where I was just ready to, for lack of a better word, strike a balance and try and get off the West Coast and the time difference and really maximize my time as a father.
“The ability to to get back home really whenever I can, that means the world to my kids, to my wife and myself,” Bailey said. “Throughout this process, I definitely wanted to hold myself accountable to how I felt the last couple of years and the strong goals I had to get back east and to maximize my time with my family.”
The Red Sox had to fend off a handful of teams who wanted to hire Bailey. The Marlins, Orioles and White Sox all had interest in bringing him aboard in some capacity and the Yankees even interviewed him for their bench coach opening (in a rare development for an ex-pitcher). His close relationship with Breslow, who was a teammate in both Oakland and Boston, surely helped the Red Sox land him.
“I had a handful of opportunities was very fortunate enough to be able to have the freedom to try and maximize my time at home with my family,” Bailey said. “Life’s too short to turn down opportunities like this.”
This winter, the Red Sox have made it a clear priority to put former players in key roles in the organization. Breslow is the first ex-Sox player to lead the baseball operations department since 1983. Bailey is the first Red Sox pitching coach to have played for the team in more than 25 years. That Bailey, Breslow and manager Alex Cora all played in Boston — and won championships with the Red Sox — isn’t lost on anybody.
Despite having a ring from his time pitching for the club, Bailey has a clear chip on his shoulder as he enters his second act with the organization.
“Through all of my experiences as a player from the highest of highs to the lowest of lows, our experiences in Boston are unique to ourselves but something that we can always lean on when we need to and go back to those as well and help our players, through good times, through great times, through bad times,” Bailey said. “We won world series and we finished last place. I experienced both of those and so I’ve ran the gamut in Boston as well in a really short period of time.
“I couldn’t be more privileged for the opportunity to be the pitching coach of the Boston Red Sox and selfishly have success because I know that I know what failure feels like in a major market and in Boston specifically. And I’m super pumped and stoked to to have that opportunity again.”