Red Sox

Red Sox

Ten years ago this fall, Eddie Romero and Brian O’Halloran stood in the elevator of the Westin in Denver.

O’Halloran’s fuzzy on the exact time, because it was so long ago. 

Yes, we’ll go with that: because it was so long ago.


The celebration from the 2007 World Series was tapering off.

“Sort of in a quiet moment, hours after we won,” O’Halloran said. “There were other people in the elevator. It wasn’t all Red Sox personnel.”

No warning came in close confines. 

“Just poured a beer directly over my head,” O’Halloran said. “I had champagne and beer on me from hours earlier. I was dry — on the dryer side — and I think he was concerned that I was angry at him. But I wasn’t. 

“When we won in 2007, we had some fun celebrating, and I think we may have replicated it in 2013.”

As Romero put it, O'Halloran was "way too dry."

"And I like celebrating," Romero said. "Anyone can tell you that."

Including the entirety of the elevator.

These two are still on the ride together today, one stop from the top. O’Halloran, a 45-year-old from Weymouth, Mass., and Romero, a 37-year-old from Puerto Rico whose dad played for the Red Sox, are assistant general managers.

That places them second in the Sox hierarchy, underneath president of baseball operations Dave Dombrowski. 

O’Halloran’s going into his sixth year with this title, while Romero’s entering his first. The former is known primarily for his contract and rules work, the latter for international scouting. 


People talk about Moneyball and Big Data in baseball. Both topics fit a larger concept: the era of the front office.

There’s a reason Fortune just ranked Theo Epstein the world’s greatest leader in any endeavor. (Yes, ahead of the Pope.)

Epstein doesn’t go it alone, though. Neither does Dombrowski.

And the top two Red Sox lieutenants are quite the pairing.

How Romero and O’Halloran ended up in these jobs after starting off so far away from baseball; why O’Halloran hasn’t moved up even further yet; what led to Romero’s promotion, despite a scandal in his department last year — Dombrowski’s right-hand men are a lot more interesting than the big boss himself.


Brian O’Halloran’s father, Jim, passed away in August. This season will be his son’s 16th year with the Red Sox.

Jim was a union printer for 40 years. He started with the Boston Record, one of the papers that eventually folded into the Boston Herald.

His son, however, wants nothing to do with the news-making business.

There’s modesty, and then there’s a direct avoidance of the spotlight. O’Halloran, known around the Red Sox as BOH, operates with the latter.

With a slight edge that reflects his intelligence, O’Halloran stressed about 18 times how many people beyond him and Romero make the Red Sox run.

O’Halloran watched Wednesday’s spring training game with his mother, Mary, a former teacher in Weymouth. 

O’Halloran was directly inspired by his mother’s work.

“One of her close teacher friends was an art teacher, and noticed in kids’ art at the time … a sort of fear of the Soviet Union and nuclear war,” O’Halloran said. “My mom and several other teachers kind of got together and they decided to try and foster some interaction between regular people, particularly kids of the two countries.”

They started an exchange program with the Soviet Union, bringing different groups of kids to the U.S., and to Weymouth, and vice versa.

The first group that came over was from Georgia. The Republic of — not the Peach State.

“I didn’t know what Georgia — I mean, maybe I had heard of the other Georgia, I didn’t know,” O’Halloran said.

His Weymouth school offered Russian, so in his senior year, O’Halloran started to learn it.

Within a few years, the Irish kid from Boston became fluent in Russian and Georgian, languages that are entirely different from each other, never mind English.


Eddie Romero’s first language is Spanish, although you wouldn’t know it. He still oversees the Red Sox’ international scouting department, the job description he had before Dombrowski promoted him this offseason after a year of some controversy for Romero. 

A native of San Juan, Puerto Rico, Romero was easy to spot this spring training in a World Baseball Classic pullover. He didn't hide his allegiance.


Romero would’ve been harder to pick out at Fenway Park in the late 80s, but he was there, always.

Romero’s father, Ed Romero Sr., was an infielder with the Red Sox from 1986-89.

“I used to come with him to the ballpark every day at Fenway,” Romero Jr. said. “I used to run around Fenway with like Dwight Evans’ kids…and Bob Stanley’s son. You kind of grow up and you think, like, everybody has buddies at the ballpark.”

A dream life, to be sure. 

But he had to stay home during the 1986 World Series, with his grandfather. His mother went, he did not.

“I obviously didn’t think it was fair back then — I wanted to go, I was 7,” Romero said. “I remember when everything happened and they lost Game 6. I was with my grandfather on the couch, and I just remember it like yesterday: absolutely bawling. That’s just something that you never forget.”


The tanks are also hard to forget. 

Inspired by the Georgians he met in high school, O’Halloran kept studying Russian in college at Colby. He took an eight-week intensive course in Georgian at another campus, too.

Twice, O’Halloran wound up in Georgia, the second time on a fellowship to study ethnic conflict and democratization.

He literally saw tanks roll down the street.

“Tbilisi, Georgia, so the capital city of Georgia,” O’Halloran said. “When I was first there in the fall of 1991, they were trying to overthrow their government. And so there were demonstrations in the street, and the government kind of cracked down."

Classes were canceled, although daily lives weren't entirely interrupted.

After college, O’Halloran wanted to keep working internationally. He went to Washington D.C., then on to Russia, hooking up with a logistics company.


Romero always wanted to work in baseball. Doesn’t everyone? But he also had an eye on law school. An internship with the Brewers in 2002 led to some thought of going to law school in Milwaukee at Marquette.

Romero instead went back to the University of Florida, where he did his undergrad work. (He’s still crazy about the Gators.)

While trying to keep irons in the baseball fire, Romero took work. 

Not in corporate law, not at a non-profit — but in Jacksonville, Fla., at the state attorney’s office. As a prosecutor.

“Being a first-year guy, it was mainly misdemeanors,” Romero said. “Domestic violence cases, smaller drug offenses. DUIs. And you grow up pretty quick when you’re dealing with a lot of victims and talking through scenarios and trials and all that stuff. 

“There was a competitive aspect that I liked to it, but there’s also a kind of honorable, civic duty that you’re performing… [That job] makes me appreciate what I do now that much more.”

It was also a duty that he had to break, when he got a phone call that the Red Sox were interested in the resume he sent. 


He wasn’t a full year into the Florida gig.

“I was very nervous about talking to the state attorney when I told him I’d leave,” Romero remembered. “Because you sign up for a couple years. And he was a huge Red Sox fan. That helped so much relieve the stress of having to tell him that I really wanted to take this job.”

Romero said he still has an active license.


As his 20’s wound down, O’Halloran was in Moscow and realized he just didn’t have a passion for his line of work. He was handling work for U.S. government contractors, for oil and gas mining companies doing business in Russia. 

He was always a Red Sox fan. An MBA program at UCLA led to a connection and then an internship with a guy named Theo Epstein in San Diego.

But O'Halloran didn't waltz into a fancy job.

“I finished my internship with the Padres,” O’Halloran said. “I was about to get married. My wife to be was starting a master’s program at Harvard. We wanted to be in Boston if we could both be in Boston.

“I was obviously in touch with Theo, because he had hired me in San Diego. At that point they had three baseball operations interns: and that was [now Cubs GM] Jed Hoyer, [now Diamondbacks assistant GM] Amiel Sawdaye, and [now Sox chief marketing officer] Adam Grossman. So, they didn’t have another spot. But he said, ‘Hey, if you want to come in at night when Jed goes home, cause that’s the only computer you’ll be able to use, he usually goes home after the game or at 11 o’clock.'”

BOH accepted. He charted games. After about a month or so, they let him start coming in during the day. How generous.

He wasn’t paid for roughly six months, though.

Romero, meanwhile, started out in international scouting in 2006, climbing the ranks. The same year that O’Halloran became an assistant GM, in 2012, Romero became a director of a department that last year found some bad press.


In some ways, Romero and O’Halloran were both ahead of the curve. They had skills applicable in other industries, and other careers, before coming to baseball. 

That’s a more common track in the game today than it was when they broke in with the Sox.

Their paths since are more complex.

Romero’s been to 40 or so countries, running out of pages in his passport more than once. 

“How could you beat traveling the world and looking for baseball players as a job?” Romero said.

O’Halloran specialized too, in some ways, focusing on contracts, transactions and administration. But he's had wide-ranging experience in others.

O'Halloran went to scout school. He was involved with the medical side for a couple years. There isn’t a part of the front office he hasn’t touched, although he’s never been directly a part of player development in the way that Ben Cherington was once the farm director. 


“I sort of help in a lot of different ways, with different staffing issues and different departmental issues,” O’Halloran said. "Interdepartmental issues, meaning, the different baseball operations departments, like amateur scouting, pro scouting, major league operations.”

O’Halloran knows the collective bargaining agreement inside and out. Romero, born from a scouting background, is broadening those horizons now. 

The older assistant GM’s the teacher, the newer the student.

O’Halloran’s very process-based, while Romero’s more impulsive — the latter out of necessity in the international amateur world.

Beers in elevators tell you everything.


Two things jump out.

One, O’Halloran’s never interviewed for a GM job anywhere. That will change.

Two, Romero was promoted to AGM just months after his department was involved in a precedent-setting scandal.

Romero was still the international director last year when the Red Sox were punished for impermissible signing-bonus practices in 2015. MLB voided five signings the league deemed the team should not have been able to make. 

In short, the Red Sox were supposed to be able to give an individual player no more than $300,000. MLB — with the help of an informant — found players were receiving more than that via re-distribution of bonuses amongst signees.

The Sox felt they were singled out for something a lot of teams did and still do.

“He paid the price,” Dombrowski said of Romero. “We paid the price. I understood the situation…I thought Eddie handled himself well. 

“I understand how Latin America works. I could not condone what took place. But the reality is I think Eddie’s a very good person and also does his job very well.”

Romero did not want to discuss what happened, other than to say it was a difficult time and that he appreciated the faith placed in him.

O’Halloran, meanwhile, has seen many former colleagues move on to prominent jobs. 

He’s been a constant in Boston, but with teams hiring younger executives, some far less experienced than him, it begs the question: why not him?

“He is very knowledgable,” Dombrowski said. “I would gather that he’s come up through the contractual administrative rule aspect of it, so sometimes that’s not the area where people reach out for the general manager aspect of it. But I can’t say that for sure.

"We signed him to a long-term contract. I think the world of him, he assists me in everything.”


Neither O’Halloran nor Romero hinted at any remorse that they didn’t stick with their prior life. O’Halloran doesn't wish he were a diplomat, Romero doesn't miss case work.

Now, as Dombrowski begins his second full year, they’re crucial figures for the Sox.

But their prior lives are still relevant. Both men, notably, studied and witnessed conflict in detail. 


"One of the things that going to law school teaches you is alternative ways to attack problems," Romero said, "and dispute resolution."

Both have agreeable personalities.

“We were at the winter meetings in Dallas,” the Diamondbacks' Sawdaye recalled of his time with the Red Sox. “We took a cab, like a van to dinner. I can’t remember, there might have been five or six of us. Brian was sitting up front, or really close to the front. 

“I don’t really recall how he figured it out. … Next thing you know, Brian and the driver are like going off laughing, talking Georgian. And the guy wanted to introduce him to his family. Literally, like, a 10-minute cab ride where he made this new best friend.”

Romero and O'Halloran were long shots to ever end up in the same room together. Colleagues for a dozen years, they're sharing a different ride now.