Why the Red Sox front office gathers in the stands at Fenway during postseason games

May 03, 2024

A quick glance at Field Box 44 behind home plate during this series with the Astros might appear to show a regular group of fans taking in postseason baseball at Fenway Park.

But the roughly 30-person pack is far from ordinary. Blending into the crowd is the scout who helped identify a young Rafael Devers in the Dominican Republic; a former scouting director responsible for drafting Tanner Houck and Christian Vazquez; an analyst who played a key role in crunching the numbers on Kiké Hernandez flourishing in an everyday role; and a pro scout who envisioned Kyle Schwarber making an impact as a trade-deadline pickup.

Throughout the season, Field Box 44, otherwise known as the scout section at Fenway (the section of seats portioned off for pro scouts from opposing teams in town for advance work) typically houses two rows of scouts from other clubs, along with a handful of Red Sox front office personnel.

But the postseason is different.

Come October, the section expands to five or six rows and serves as the gathering place for much of the Red Sox brain trust, who take in the games together as a bonding experience after a long season. The group includes VP of pro scouting Gus Quattlebaum, VP of scouting Mike Rikard, director of pro scouting Harrison Slutsky, director of amateur scouting Paul Toboni, director of major league operations Mike Regan, coordinator of major league operations Alex Gimenez, director of international scouting Rolando Pino, director of baseball analytics Joe McDonald along with several other scouts, analysts, player development personnel and baseball operations staffers.

It even includes general manager Brian O’Halloran.

“There’s always something to be worked on,” said Regan, who started with the team in 2010 as an intern. “But there’s definitely an understanding once the playoff games start, the common denominator with all of us in baseball operations is all of us love baseball so what better way to feed that passion than sit down and watch every pitch of a playoff game?”

For O’Halloran it’s a tradition that started in 2003, the first year the Red Sox made the playoffs after he’d been hired the previous year as a baseball operations assistant.

“In 2003, we didn’t even have a suite, we all sat down there,” O’Halloran said. “(GM) Theo (Epstein) sat down there, (assistant GM) Jed (Hoyer), it was a much smaller group of us. And actually back then I was also doing the radar gun, so I had to sit down there, at least for some games, and so that’s where we all sat back then.”

During the regular season, O’Halloran typically sits in the front office suite, about 100 feet above home plate on the third level of Fenway, with chief baseball officer Chaim Bloom, assistant general managers Eddie Romero and Raquel Ferreira and senior vice president of baseball operations Ben Crockett. It’s not feasible to sit elsewhere as the group monitors minor league games and discusses potential organizational moves, signings, injury concerns or any of the other host of issues that come with running a major league team. But while most of that group remains in the suite come the postseason, O’Halloran sticks with his tradition to head to the stands with their larger front office contingent.

Over his 19 years rising through the ranks with the Red Sox, O’Halloran has witnessed four World Series and some of the biggest moments in franchise history from the seats behind home plate. Yet camaraderie is the biggest reason he prefers to be among the people come October.

“There’s definitely an element of ‘I’ve always done this so I’m going to keep doing it,’” he said. “I enjoy the camaraderie of the group that helped us get there and all working together to achieve a goal, and it’s fun to be a part of this larger (thing), hearing the fans and being a part of the crowd. I grew up a fan, it’s fun.”

His teammates appreciate it.

“It’s awesome having him down there,” said Rikard, who joined the Red Sox as national crosschecker after the 2004 season. “We’ve been through four general managers together and he’s always been such a calming presence and to have him down there amongst us for those games when everybody’s nerves are ratcheted up and things are going crazy and you can lean on him and crack a joke, tell a story, he’s always been such a calming presence on the staff and just to have him in there with us is really cool.”

This postseason, O’Halloran has been seated next to Regan and in front of Rikard. Gimenez is in charge of doling out seating assignments. And while there’s generally not strictly assigned seating, Gimenez tries to group departments together. On the other side of Regan, sits one of the team’s senior analysts Dan Meyer. Regan enjoys Meyer’s perspective on some of the in-game matchups that he wouldn’t normally be as locked-in on otherwise.

“I think it’s important we all get to know each other,” O’Halloran said. “That analysts get to know scouts, that player development staff get to know people in other departments or sub-departments of baseball ops, the more you get to know each other the better you understand their perspective, and in leadership, we have to really take care to do that. I’ve always enjoyed the different perspectives.”

While the Red Sox contingent is a bit smaller at the start of the playoffs as more seats are needed for out-of-town scouts, there are only two opposing teams left that need to send scouts to Fenway, the Dodgers and the Braves. The Dodgers have six scouts here while the Braves have two ahead of a potential World Series match-up with Houston or Boston. But Gimenez is mindful that his own superstitious group hasn’t wanted to change their seating arrangement since their wild-card win at Fenway over the Yankees two weeks ago. So O’Halloran has remained next to Regan. Gimenez tries to squeeze in as much of their staff as possible, including the interns who run Trackman behind the plate.

“The other thing is, since we were last in the postseason in 2018, our staff has grown so much,” Gimenez said. “So this is really a cool opportunity, especially after the pandemic where until a few months ago a lot of us had never even met in person. So it’s really good for a group bonding thing to be down there together celebrating and enjoying this.”

As far as tickets go, yes, there was a time not long ago that the GM of the team had to show a ticket at the gate to get to his seat. Due to COVID-19 and the desire for fewer points of contact, Gimenez now emails seating assignments to each of his colleagues, which they in turn show at the gate.

“It’s tough because I like having the ticket, especially for a playoff game,” Gimenez said. “I have all my tickets from the 2018 World Series run. So we haven’t done that this year, but it makes it a little easier and a little more COVID-friendly for sure.”

While they’re not singing and swaying to ‘Sweet Caroline’ in the eighth or doing the wave when it comes their way, they do have some other traditions.

“One thing that’s cool, too, is you’ve gotten to know the vendors,” Regan said. “I’m from here and one of the vendors was in my wedding and another I grew up with. They’re walking by and we’re giving fist bumps to them.”

The pre-existing relationship with some vendors in the section is key for when the group decides to deploy their Rally Dog tactic, a pseudo hot dog eating competition they indulge in to rally the team. For instance, they chowed down on Rally Dogs in extra innings of Game 3 of the division series against the Rays. The Red Sox went on to win on Christian Vázquez’s walk-off homer.

“It’s kind of been a long-standing tradition back to the Theo years,” Rikard said. “Next thing I know the whole section is crushing a hot dog as rapidly as you can get one of those hot dogs down without choking.”

There’s fun and stress and anxiety just like for any fan, but for obvious reasons this group is a bit more invested in the outcome of the games. In 2013, as an improbable Red Sox team was pushing through the postseason, a particularly exciting moment in one of the games nearly sent Rikard to the hospital as Quattlebaum, jumping up and down in excitement, elbowed Rikard in the head.

“I told Gus the other night I was glad I was two rows behind him this year because he can get vicious in there,” Rikard said jokingly.

The long hours spent building this team, one that no one anticipated would reach the playoffs, let alone play deep in October, have paid off. And enjoying these moments as a group is what it’s all about.

“I caught myself daydreaming last week about how putting together a winning team in the postseason takes a culmination of so many people’s efforts,” Rikard said. “To be able to sit there with guys from our international staff and our pro scouting staff and our GM and then when you win, you start bear-hugging everyone and high fiving and going crazy. It’s a culmination of so many people’s efforts and hard work and really, through many years. It’s kind of that one time you can huddle up together.”

(Top photo: Maddie Meyer / Getty Images)

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