The Sunday Baseball Column: The story of how Brian O'Halloran became the Red Sox' new GM


It was Halloween night, 2002. A group of Red Sox interns that included current Arizona Diamondbacks assistant general manager Amiel Sawdaye and Adam Grossman, the Red Sox' modern-day Chief Marketing Officer, had sauntered back to the Fenway Park offices in between a full day of work and a night of holiday celebration. It was around 11 p.m.

"The cubicles were really high so you couldn't see who were in them," remembered Sawdaye. "But we kind of heard some typing."

It was worth a look. What they found was an image that has helped define Brian O'Halloran to this day.

O'Halloran, a 32-year-old who was rolling his occupational dice as an unpaid assistant, was sitting at a desk sifting through VHS images in order to log a game from the Red Sox' Triple-A team in Pawtucket. But that was only half the story. The man who wasn't allowed to work during the day due to a lack of cubicles was conducting his task while dressed in his Halloween costume.

The guy whose baseball career ended with one year of junior varsity ball at Weymouth South High, held degrees from Colby College in political science and Russian studies and once found himself as the last American to leave the country of Georgia during one of its civil wars had left an impression among the cramped quarters at Fenway Park. It is one that ultimately led him to the position he will officially be awarded with Monday -- general manager of the Red Sox.

"That moment spoke to his work ethic," Sawdaye said. "It speaks to who he is.

"People who have been around him know from a management perspective he leads by example with an indefatigable work ethic. He has a really strong presence in the offense, just keeping everyone together. He’s just very grounded. There aren’t a lot of ups downs with BOH. He has a really good way about him to defuse the situation. He’s a really good listener, also. It’s what makes him a strong candidate for that job and really any job in baseball, for that matter."

While most of the focus at Monday afternoon's press conference will understandably be on new Chief of Baseball Operations Chaim Bloom, the story of how O'Halloran landed as a GM should absolutely be highlighted. 

- First position out of college was in the Georgia capital of Tbilisi where he was awarded a fellowship to study ethnic conflict.

- First paid job out of college was working for an international logistics company, which sent him to Russia for three years. (He speaks both Russian and Georgian fluently.)

- Came home and sent letters and emails to anyone associated with baseball, ultimately landing in the Pawtucket Red Sox' group sales department for a summer while helping out at Woolf Associates law firm.

- Enrolled at UCLA in order to attain his MBA.

- Hired as a baseball operations intern by the San Diego Padres.

- Moved back to Boston so his wife could pursue her master's degree in language and literacy at Harvard.

- Was allowed to volunteer in Red Sox offices at nights and on weekends.

- Was hired in Jan. 2003 as Theo Epstein's administrative assistant.

- Spends 16 years with the organization in a variety of roles, most recently serving as an assistant GM while focusing heavily on contract issues.

- 2019: Becomes Red Sox GM.

O'Halloran's nose-to-the-grindstone and unassuming persona often times left him out of the conversations for the kind of position he has finally found himself in. But those who have witnessed him since that Halloween night nearly 17 years ago -- whether in the midst of contract negotiations or letting his oft-hidden competitive nature emerge on the basketball court ("He’ll dive for everything, skin up his knee, cut his face and just keep going. Obviously he’s very driven both athletically and in the office, you just don’t see that side of him," Sawdaye said) -- isn't surprised this is the latest chapter of a pretty remarkable story.


Bloom's strategy heading into his first offseason with the Red Sox will be largely pushed by J.D. Martinez's decision to either stay with the Red Sox or opt-out of a contract that is currently guaranteeing him $62.5 million over the next three seasons.

In baseball circles, the conversation has surfaced plenty of debate.

The consensus continues to be that the most logical suitor for Martinez would be the White Sox, with the Rangers another American League possibility. It's still difficult for many to envision a National League team jump into the fray considering the 32-year-old's defensive limitations. But there are two factors which should potentially be dug into a bit more:

1. If Martinez opts out of his deal the Red Sox will undoubtedly extend him a qualifying offer, meaning any team that signs the designated hitter/outfielder would have to surrender a draft pick. As we have seen plenty of times in the past that would be just another deterrent for teams potentially already sheepish about investing heavily in a player with the age and skill-set of the slugger. (Since 2012 80 players have received qualifying offers with just six accepting the one-year deal.)

2. Martinez's agent Scott Boras is going to control this offseason. What this means is that there will be less room for interpretation when it comes to which free agent might go where. The three biggest free agents starting next month -- Anthony Rendon, Stephen Strasburg and Gerrit Cole -- all are represented by Boras, as are Nick Castellanos, Dallas Keuchel, Mike Moustakas and Hyun-jin Ryu. There is some thought that if Martinez does hit free agency Boras will prioritize getting the righty hitter's new deal done on the earlier side.


Prior to participating the Diamond Resorts Tournament of Champions golf event this week, Lester weighed in on how he viewed the game, particularly when it came to watching the difference in the baseball from the regular season to watch we're watching in the postseason.

"I think we need to figure out a constant with that," said the former Red Sox pitcher. "I think that will benefit everybody. I think you’re seeing even hitters in the postseason right now hitting balls that they hit during the season that were home runs and now they’re putting their arms in the air saying, ‘What’s going on?’"

Looking at the numbers thus far in these playoffs it's hard to argue with Lester's analysis. In a year that blew away the record for most homers hit during the regular season, the postseason total will end up shy of both 2011, 2015 and 2017. To give an idea of the difference, in both 2011 and 2015 the MLB home run total was under 5,000 for the regular season. This past regular season, conversely, ended up with 6,776 homers.

As for Lester, he is entering an interesting season in his career. First off, his personal catcher and good friend David Ross is now his boss.

"I think we’ll be fine with the relationships," said the lefty. "We’ll be fine. You just have to find the place and the time and I think the communication will be good for everyone involved."

Lester is also going into the last guaranteed year of his contract with his AAV jumping from $15 million in 2020 to $25 million in 2021 if the Cubs pick up his option. The option will, however, vest if the soon-to-be 36-year-old pitches 200 innings in the coming, a total he hasn't reached since 2016. Lester finished this past year with an ERA of over 4.00 (4.46) for the first time since 2012.


Talking to people throughout baseball the consensus is that one of Bloom's strengths is his willingness to listen while not giving off a my-way-or-the-highway mentality. Perhaps an example of that could be found when the then-Rays exec appeared on the Executive Access podcast with's Mark Feinsand.

"You hope there would be times you disagree," Bloom said. "I think that’s what you want in a healthy organization. You want to have disagreement. I think it’s no different when we might have a disagreement within our staff, or one staff member to another. If you have people who have the right intentions and the right goals in mind you can discuss those disagreements with each other and push each other. At the end of the day we have to make a decision but that doesn’t mean those disagreements aren’t productive and hopefully, something good comes out of them."

This quote regarding uncovering the kind of advantages Tampa Bay seemingly routinely discovered was also telling.

"I think right now in this game you have 30 organizations searching for that next advantage and they are doing that at a more rapid pace than they ever have," he noted. "What once might have been the domain of a few small-market teams or some more innovative larger market clubs is now a 30-team race. We’re always challenging each other and pushing each other and pushing our staff to say, ‘What is going to be next? What is the game going to look like in five years, 10 years? What does that mean for us and how are we going to continue to find those advantages that set us apart?’"


For a few minutes during those Winter Meetings leading into the 2017 season it looked like Sale was headed to Washington. The Nationals had offered the White Sox a package of pitchers Lucas Giolito and Reynaldo Lopez along with outfielder Victor Robles in exchange for the lefty pitcher. At the time the trio of players was Washington's top three prospects. The deal-breaker for Chicago ultimately was Washington's unwillingness to part with shortstop Trea Turner.

We know what happened, with the Red Sox swooping in and getting Sale with a four-player package that was highlighted by Yoan Moncada and Michael Kopech. (Dave Dombrowski smartly rebuffed White Sox GM Rick Hahn's attempt at including Rafael Devers.)

The Nationals ultimately used Giolito and Lopez to get outfielder Adam Eaton, avoiding having to include a rising star in Robles.

While it is understood that Sale helped win the Red Sox a World Series and the Nationals have landed in this year's Fall Classic, let's do this: Just for fun, ranking the 2019 value each player mentioned had to their team:

1. Devers

2. Moncada

2. Giolito

3. Turner

4. Robles

5. Eaton

6. Sale

7. Lopez

8. Kopech

Discuss ...


- While many will remember the morning this column is being published as the one-year anniversary of the conclusion of the Red Sox' 18-inning loss to the Dodgers I will forever classify Oct. 27 for something else: When the Dodger Stadium press box served an unfathomable 800 Dodger Dogs to media members.

- When it comes to the Astros and the case of Brandon Taubman's stupidity, one thing that Houston and Jeff Luhnow can't wash away is this: Their true, down-to-the-soul feelings were cemented with the attempted takedown of Sports Illustrated writer Stephanie Apstein's credibility. Luhnow admitted many people reviewed that statement put out following Apstein's story documenting Taubman's vile behavior, including Luhnow himself. To repeat: Luhnow is admitting signing off on something that we now know he simply wanted to be true. Major League Baseball will come out with a ruling on the situation after the World Series, but there is absolutely no doubt a significant message should be sent the way of Luhnow, whose warped priorities have truly been exposed.

- This is a rule for 2020: "All pitchers must face at least three batters or end a half-inning, unless injured." This is the reality of the 2019 postseason: There have been 58 instances this postseason where a pitcher has been on the mound to face fewer than three batters.

- When comparing Terry Francona, John Farrell and Joe Maddon on the Bradfo Sho podcast it was interesting to hear Ross describe how Francona handled things with the Red Sox. "The thing that stood out for me with Tito is that he seemed to be everybody's friend. He was a guy who was easy to talk to. He communicated well. Him and Bobby Cox were the only two managers I've ever played for who were out on the bench early, sitting hanging out, talking to the players. Just one of the boys. ... Just being able to go into his office and it was very simple. He said, 'We don't have a whole lot of signs here Rossy. Behind the plate get an out. If I tell you to throw through we're going to eat it. We don't bunt here. We play our nine guys against their nine guys. You're going to feel right at home here in two days.' Just the simplicity of that and just how comforting he made me feel right off the bat. ... He's one of the guys when he talked to you. He doesn't beat around the bush and is pretty straightforward."