Mike O’Brien ‘23

Chief Sports Editor

Graphic design by Hui Li ’21.

Sports are one of the most cherished facets of life as a Holy Cross student and alum, and perhaps nobody knows this better than Michael Philbrick ‘96, an HC graduate with a degree in history.

A senior editor at ESPN, although Philbrick wasn’t a varsity athlete himself, he’s an aficionado of HC Sports past and present with the experience of an intramural basketball player to boot.

In a conversation with Michael over Zoom, I was able to pick his brain about his career, his time as a Holy Cross student, and a number of other ranging topics.

I started by asking him what a typical day is like working at ESPN. Currently working with ESPN’s podcast content, ESPN Investigates, he responded “A typical day relies on whatever part of the process we are in. We work a lot with our storytellers, which are our reporters out in the field. As you get into audio-based storytelling, it’s very different from writing or television.

“Right now, we’re looking at a few stories that have either been told or are being told and how they can have an audio element; but then also planning into the future. I’m working on a story right now on how we can really own the sports angle of audio storytelling for the twentieth anniversary of 9/11. 

“I have a story pitch that really wants to focus on the origin of the Super Bowl Halftime Shows. If we do go through with it, it wouldn’t be for the Super Bowl coming up, it would be for the one planned in 2022. These really are like television shows; although we don’t have the lights and the cameras, they’re equally as involved.”

Hearing about the emphasis that Philbrick and his colleagues place on the true essence of storytelling within the realm of sports, I followed up by mentioning that while ESPN and SportsCenter started off as a television show that simply recapped the sports events that had just happened the night before, the storytelling angle of the company has truly progressed.

Along with ESPN Investigates, there are also ESPN 30 for 30’s which plunge into a topic with the same storytelling drive within a visual format, along with the recent success of ESPN’s documentary series telling the story of Michael Jordan and the Bulls’ final season together, “The Last Dance.” I asked Philbrick how exactly ESPN has progressed from a sports news recapper to a network that truly seeks to tell sports stories.

Philbrick responded “It’s merging us being a storytelling company, at its heart (which is what the Walt Disney Company is) with being a technology company, meaning that we can bring you original content on platforms like ESPN+ straight to you by harnessing what streaming has turned into today. As where it used to be we had no place to put it, if now you want to see a 30 for 30, head on over to ESPN+ and you can see it right now.

“We’re able to maintain the same level of storytelling that we’ve had back when they would do something like an investigation back in 1985, but we’re able to maintain people’s eyes and attention because we’re able to be on the cutting edge of technology.”

Keeping on the theme of storytelling, I replied that as a sports journalist, there seems to be a big difference between writing and editing. As a writer you’re telling your own story, while as an editor, you’re helping someone else tell their story the best way that they can. I asked Michael that as an ESPN employee, does he prefer helping other people tell their own stories as an editor, or telling his own stories as a writer?

Michael responded “The way I always put that is if you had asked me ‘What’s your favorite Star Wars or Marvel movie?’ my favorite one is the fact that I can watch a variety of them. And so that’s why I could never just write about baseball or football. In the same respect, I don’t think I could just be an editor without knowing that I could create on my own in my back pocket at times. But, I do like the process of being an editor a lot, because I feel like there’s more responsibility to help something look really amazing. 

“Helping the writing process be as smooth as possible is great, so when a person’s name is on an article and they’re completely proud of how it came out, knowing they put their faith in you and you delivered is really rewarding to me. My thing is I need to know what angle you want, because that passion is going to very clearly come across in what you give to me. When the content creator is passionate, it’s always a better product.”

I was interested in talking about the pieces online that did have Michael’s name on them as well. One of the pieces that I especially enjoyed was a 2004 article about Michael’s day with a street basketball player named Trickz, and how he helped Michael to look the part of a true street baller. While it’s mostly a fun article, there are some pieces that I found compelling, such as Michael’s mention of a phrase I acronymed B.Y.O.A., or Bringing Your Own Attitude, when it came to playing on the courts. While that was in a street ball sense, if we’re talking about sports journalism, how should sports journalists looking to break into the field look to bring their own attitude into their pieces?

Michael responded “When it comes to breaking the field, in 2020 the thing that is truly unique and lucky for people who want to get into the journalism field compared to those studying to be an accountant or a lawyer or a doctor, those people definitely need to be given some sort of a platform where you’re getting feedback from professionals regarding ‘Am I doing this right?’ However, if you wanted to write about the crossover between sports and music, you could start a blog where you are the known source for it, and it teaches you a lot. The second you hit publish, granted as many people could see that as possible, it takes a leap of faith and it’s a great opportunity to put yourself out there, and get feedback on pieces, good, bad, and ugly.”

Something that Michael mentioned that stood out to me was the fact that if you ran through the list of majors at Holy Cross such as accounting or getting on the pre-law or pre-medicine track, there’s generally a pretty clear cut path that allows someone to succeed in that field if they put the time and effort into it. Being an English major myself, one of the more ambiguous career paths coming right out of school, Holy Cross isn’t like other institutions in the sense that they have specialized programs for journalism that helps to provide a direct path to working in a journalistic field after graduation. So I asked Michael, since we both chose Holy Cross and we’re both interested in sports journalism, how did he think Holy Cross helped to prepare him for his current career within the world of sports journalism better than another institution could have?

Michael responded “What I say to that is if you take a student from Holy Cross and compare them to students who entered a specialized program for journalism at another institution, what happens if you both suddenly decide ‘I don’t want to do this?’ I don’t see students with specialized degrees in journalism having a huge leg up in my industry, and in the hiring process we look for the people who have studied in the liberal arts background of writing, thinking, and speaking effectively in multiple disciplines. 

“I’m not trying to tell students of a university with a specialized journalism program that they’re doomed, but you’re going to find yourself in the first 15 years of your career not being as versatile as liberal arts students would be. The difference now is that you need to be a jack of all trades. I think that my experiences in school helped prepare me for being able to communicate effectively with people who have different roles from my own. Coming into the workforce out of school, you need to have the attitude that you are humbled, but empowered, knowing that there is no task beneath you or above you. And I feel that these kinds of values are more learned at a place like Holy Cross compared to other institutions.” 

Staying on the theme of Holy Cross, Philbrick had published an article about Holy Cross’ football team with legendary players like Gordie Lockbaum playing under Coach Rick Carter, and how Carter tragically lost his life to suicide after a fight with depression. Using the article and other events as inspiration, I asked Michael how he believed that Holy Cross student athletes past and present are able to be so resilient in the face of tragedy and adversity.

Michael responded, “I think it’s because it’s a family. If you see someone wearing HC apparel in public and you compliment them on it, you instantly become friends. When you have that connection that just seeps into you during your time there, there’s that feeling of being part of something bigger than just yourself. When I talked to Geordie and quarterback Jeff Wiley about that whole course of events, when they got together, there was a sort of military mentality that everyone stops feeling bad for themselves, and instead they focused on being there for everyone else there in the room. When you have these ideas woven together, that’s the same response you get to what happened to Grace Rett. That’s why the women’s crew team and football team knew they would bounce back from the events that happened to them. Within this family, you know anyone wearing purple has got your back.” 

Being on the cross country and track and field teams myself, we’ve obviously never had to deal with tragedy on the magnitude of the events mentioned above, but due to the pandemic going on, it has drastically changed our dynamic as a team. However, we’ve stayed in touch so well because I think Michael is absolutely right in the fact that Holy Cross and its sports teams are a family that’s strong together. I followed up on this idea with asking Michael how the pandemic has changed how he’s interacted with his team of co-workers at ESPN over the last months.

Michael responded, “I think now, whereas in the rush and chaos of a typical workday before the pandemic, you didn’t think about how they were doing. Although we are now struggling through this together, a couple of months ago, we all had a family member or friend who was struggling with something just as heavy, but on an individual level. I find that now we are more connected because we’ll just reach out to check in with each other. Not writing to them about something regarding the podcast, but instead asking how they’re doing. And meaning it.

“I’m sure as you can speak to this with athletics, there is a difference between how you can carry yourself emotionally and physically while playing sports or working on a group project for a job, if there are peers and superiors who are empowering you.”

Michael’s attitude towards staying connected with others and checking in on their mental health struck me as him being an optimistic person, and I wanted to see if this applied to the sports journalism field. Many people point to Bill Simmons, an ex-ESPN employee and fellow Holy Cross alum himself, for helping contribute towards the death of sports journalism. One of the main criticisms is that his site, The Ringer, is too media and pop culture orientated without focusing on the actual meat of the sports stories themselves. So I had to ask Michael– did he believe that the industry is dying or was he hopeful that the industry can continue to thrive in the future?

Michael responded, “Well first of all, I was Bill’s editor for 14 years, so I’ve seen all sides of this argument. But I think it kind of goes back to what I said about our company as a whole and adapting to the way things are consumed, from a technology basis. With the fact that you can set your phone to know instantly what’s going on during the game, the ability to access that doesn’t mean that the storytelling is dying, it means that the storytelling is changing. Look at how popular storytelling podcasts have become; this just means that things are changing.

Although I understand sides of the argument against Bill, at the same time, journalists who believe the industry is dying are evolving more than they care to admit. There are people in the industry like myself who have started learning how to make HTML and learn graphic design to be able to keep up with the evolution of the industry. I don’t think it’s dying as long as people keep reading, watching, and listening to it.”

With the idea of willingness to learn in mind, it reminded me of something Michael said earlier about taking a leap of faith when it comes to breaking into the industry. This leap of faith relayed back to the last article of Michael’s that I read, about how he came off the bench in his senior night basketball game to sink a three point shot, although dads in the crowd were literally betting amongst themselves that he wouldn’t make it. Perhaps in a poetic sense, how did he view that play as a metaphor for his career by trusting in himself and his work?

Michael responded, “Well, there could have been 10 dads, 50 dads, or I could’ve had the whole town betting against or for me, but the only person who was going to dictate what happened that night was me. And the same goes for my work.”

Michael’s shot was actually captured on tape, and his unconventional form stands out. I had to ask– did his form get a chance to improve as a Holy Cross intramural athlete?

Michael reported back negatively, saying “The problem that we struggled with is that we had our team and we were pretty decent, but my friend Brian, who refereed, was the most ethical person in the world, so if I travelled he would call it. If I committed an offensive foul he would call it. I would ask him, ‘Dude? Can you be like the other refs who wink to their friends?’ And he would say ‘No, that’s not how the game is done.’ My only problem with my basketball game in college was that I failed to hang out with an unsavory crowd. I’m going to stand by that our downfall was the people we knew were of pure Jesuit moral character.” 

To wrap things up, being the sports editor of The Spire, I feel like I have a sense that sports journalism is definitely something I’m personally interested in as a career. Although Michael didn’t write for his school newspaper in his time as a Holy Cross student, how did he get a sense of deciding that sports journalism was right for him, and what was his lightbulb moment?

Michael answered, “The lightbulb moment was when I was working for the Celtics in the fall of ‘95, and at the time we were getting all these requests for information because they were getting ready to launch nba.com in the spring of ‘96. The lightbulb moment came in the idea that your success on the internet came due to how hard you were willing to work, and I found an avenue in which I could find content I truly wanted to talk about and get paid for it; but doing it in an arena where the cream will rise. It provided, for me, an attainable path to success.” 

After our interview had concluded, Michael and I stayed on to talk and geek out about sports for a little longer. Him being a Massachusetts native living in New Jersey and myself a New Yorker, we brought up the obligatory Yankees-Red Sox rivalry, and am very happy to report that Michael has never had a bad experience donning Red Sox gear at Yankee Stadium. See, our fans aren’t all slimeballs after all. 

We also talked sports conspiracy theories, and staying on the topic of New York, Michael only has one sports conspiracy that he buys into– the NBA rigging the draft lottery to allow The Knicks to draft Patrick Ewing. Did they freeze the envelope? Did they make it sticky? The world may never know, but Michael believes that Ewing falling into the Knicks’ laps seemed to be too good to be true.

Thank you kindly to Michael for his time, and as he said, Stay Purple.