SAN DIEGO — Two walls of Don Orsillo’s office at Petco Park are covered in photographs.
It’s a veritable ‘Who’s Who’ of baseball legends and current stars he’s worked with throughout his career. Commissioner Rob Manfred, Pedro Martinez, Dennis Eckersley, and of course, his close friend and longtime Red Sox partner, the late Jerry Remy, feature prominently.
But it’s a small cloth patch smack-dab in the middle of the larger wall’s array that draws the eye. Its circular shape contrasts with the angular photos that surround it, as does the embroidery atop the black background: a large, white ‘2,’ and ‘Remy’ in smaller, red letters above it.
It’s one of the patches Red Sox players wore on their jerseys throughout the 2022 season in honor of Remy, who’d passed away the previous October after battling cancer for many years. Orsillo wasn’t able to be a part of the April 2022 ceremony at Fenway, a situation that pained him deeply.
It’s the first of many topics about which he’s an open book. He’s more than willing to discuss the mixed emotions he’s felt over the last eight years; this past weekend’s Red Sox-Padres series, in particular, was quite a collision of his past and present.
Much like the game he loves, Orsillo’s time with the Red Sox was full of triumph and heartbreak. Born in Melrose, Massachusetts, and raised nearby in New Hampshire, they were his childhood team, and he dreamt of becoming their voice. He spent almost all of the first few decades of his professional career in the Red Sox organization, first as a college intern to the legendary Joe Castiglione, then in the minor leagues, and finally, the big show.
Between 2001 and 2015, Orsillo’s voice was the soundtrack of some of the greatest moments in franchise history, and his rapport with Remy and Eckersley kept fans entertained during the less-than-great seasons. The anniversary of their iconic pizza game is celebrated each year, and he’ll often send out a tweet for the occasion or reference the moment when showing off his culinary skills.
Then, in August 2015, Orsillo got called in for a meeting on a team day off, and was told that his contract wouldn’t be renewed at the end of the calendar year. He quickly landed on his feet in San Diego, but doesn’t pretend to be unaffected by his firing.
“At the time, it was really devastating for me, because it’s all I knew. It was my dream job, my home team, and I thought I was pretty good at it, and it was going well, and I didn’t see it coming,” he says with a sad smile. “But then, I came here, and I couldn’t love it here any more. I live on Coronado Island, I fish every day, I get to work in 11 minutes, and I work at this beautiful ballpark, and the fan base has embraced me really well, almost as well, I would say, as Boston.”
Orsillo still has immense affection for Red Sox fans, but no longer counts himself among them.
“I keep abreast of all the teams, but my fandom sort of ended,” he pauses and corrects himself. “No, it didn’t sort of end, it ended when I was fired.
“I mean, how do you get fired and then turn around and root for that team, even though I had my entire life?
“And the Padres were so aggressive in bringing me here and giving me this opportunity, my entire fandom went to the Padres, and I detached myself completely from anything going on there,” he says of Boston. “For me, it was really personal. I took it really hard.”
“Kevin Youkilis reached out to me and Will Middlebrooks. They both called me, and wanted advice, my opinion. It was before they both got the job. Youk, especially, was like, do you think I can do this? I said absolutely, you have the right personality to do it.”
Youkilis and Middlebrooks have been popular additions to the broadcasts, as Orsillo knew they would be. It’s an ability he honed during a difficult time.
“There was one year that I worked with 26 different partners. It was when Jerry got cancer and depression all in the same year, and missed basically the whole year. And that’s when Eck and I started working together a lot, but I had so many different partners,” he recalls. “What we would do is we’d take the visiting team’s pre- and post-game analyst and put them on our show. When I’d go to New York, I’d get Paul O’Neil or David Cone for a game. I worked with Dave Roberts for 45 games!
“From that year, I really got a feel for who would be good at this and who wouldn’t be,” he says, “and it gave me the opportunity to work with so many people, and I really enjoyed that part of it because I got to meet all these people across baseball that I normally wouldn’t, and gain new perspective on how to do games. But I missed Jerry.”
Other than fans, family, and old friends, it’s only when his national broadcast schedule overlaps with Boston’s, or on a weekend such as this (which will be a yearly occurrence moving forward, thanks to the new schedule format) that he dives a bit deeper into his old ball pit. With any Padres opponent (or national broadcast matchup), he’ll watch several of the team’s games in the week leading up to his work with them. He admits that he’s surprised by the Padres and Red Sox, but given their respective rosters, projections, and records, for very different reasons.
“I think they’re a good enough team from what I’ve seen of them, I just think that they’re in a really tough division, so that’s going to be really hard,” he says of the Red Sox, who entered Sunday in fourth place in the stacked American League East, despite being tied for the eighth-best record in the game. “But I think the roster has performed very well to this point, they have to be happy with what they’ve gotten from this group so far, and I think they’re only going to get better when they get some of their guys back, like (Trevor) Story. They’re headed in a good direction. And Devers is Devers, obviously.”
Orsillo hasn’t seen much of Rafael Devers, but he happened to be doing the national broadcast of a Red Sox-Braves game in Atlanta last year when the slugger hit a mammoth grand slam. He repeated the performance in San Diego on Friday night, homering in each of his first two at-bats.
“I think he’s a great talent, it’s great that they were able to lock him up. He’s just a natural, raw talent, and I think he’s superstar material, could be a Hall of Famer. I think it’s great for Boston to have him.”
With so much distance between himself and his former team, Orsillo didn’t hear much about the parallels being drawn between this past offseason and 2012-13, but after unpacking the two winters, he sees some merit.
“I can see that comp,” he says, adding, “2013 might have been my favorite of the three World Series that I was there for.”
Still, he admits that the prospect of starting anew was daunting.
“I was afraid, because I was starting over again. When I first started with the Red Sox, I worried, ‘Fans may not really dig you.” And here, I came in for a Hall of Famer in Dick Emberg, and I thought, this isn’t going to be easy. But they’ve been great, and I absolutely love the fans and the team. I’m all in.”
As an expansion team, the Padres’ history is much shorter than the Red Sox’s, which began in 1901. The two franchises couldn’t be more different, but Orsillo sees some commonalities.
“This situation, to me, is similar to how I felt in ‘03. It had been 86 years, and we knew we were close. I mean, the way they lost to Aaron Boone, the walk-off, but I felt like we were right there. We were at the door,” he recalls. “That’s the kind of feeling I have right now. We’re right there. We’re at the door. And it wouldn’t be 86 years, but it would be 54 years and the first Padres championship ever. I have three rings with the Red Sox. I would like to have a fourth with an ‘SD’ on it,” he says.
If the Padres win their first World Series at some point in the next decade, Orsillo won’t be the only jilted Red Sox champion adding a new ring to his collection. He was thrilled when Xander Bogaerts signed an 11-year, $280 million contract with the Padres, but couldn’t believe the Red Sox were willing to part with him, especially given the gap between their bid and several other teams’ offers.
“I think with Xander, first of all, his resumé as a player. But then, there’s also the fact that he is such a huge clubhouse person, such a character person, that was very much something they wanted.”
He and Bogaerts go back over a decade. The shortstop signed with the Red Sox when he was 16, and made his major league debut in August 2013, when he was only 20. Even though he was one of the younger, newer players on the team, Orsillo remembers being impressed with his character early on.
“My last game in 2015 was in Cleveland, and I have the picture of everybody coming out onto the field, players all came out, and he’s right in the middle. He is the first guy I saw when I looked down there” Orsillo recalls. “He, and Dustin (Pedroia), and Mookie (Betts), and those guys will always have a special place (in my heart), because that was like, unbelievable to me. I never saw that coming, you know that anybody cared? I knew the fans did, but the team? That was pretty cool, and he was one of those guys for me.”
When trying to court an important free agent, teams will often turn to someone within their organization to help seal the deal. But for whatever reason, the Padres didn’t ask Orsillo to help them land Bogaerts, and it turned out, they didn’t need to.
It was a different story when it came time to introduce their newest star.
“We actually ran into each other before, randomly. It was planned that I was hosting his press conference, but we happened to meet in the hall first. He’d just signed his contract and was coming from one hall, and I was coming from the other hall, and all of a sudden, it was just like, ‘Hey!’
“I’m just so happy he’s here. I’m thrilled he’s here. I get to see him every day, we talk every day.”
Next year, Orsillo and Bogaerts will come to Fenway for the first time as members of a different organization. The broadcaster has been back in his national broadcast capacity with TBS and FOX, but never in this role. Despite the love he gets from fans online and in person, he wonders how he’ll feel when he returns to Fenway with his new team.
“I don’t know, I really don’t,” he says. “It’s been so long now. I mean, I wouldn’t change a thing. I loved my time there. I grew up there, I had two children while I was there, my entire family, and the experience was great, up until it wasn’t.
“But to know that fans still care, and are as warm to me as the group that just walked through here,” he says, gesturing towards the hallway where a tour group full of Red Sox fans were overjoyed to see him and pose for photos with him minutes before this conversation, “It just, it means the world to me. It really does.
“It’s totally humbling. It really warms my heart, because I was very much one of them for over 40 years,” he said. “I left when I was 46. I said my last game that I would like to be, if I’m remembered at all, that would be something very special to me. And to this day, I feel like I’m remembered, and that’s very special to me.”