In order to prevent repetitive conversations surrounding the same teams from taking place on his digital podcast, Kevin O’Connor keeps a spreadsheet where he tracks the topics discussed in each episode. Even though the indomitable cadence of breaking news often resonates throughout the content ecosystem, O’Connor recognizes the importance of giving credence to every NBA team while discussing the game for a national audience.
If six weeks has gone by without talking about a specific franchise, he will try and introduce the organization into the topic rotation for an upcoming episode. In addition to safeguarding against imbalance, something O’Connor refers to as being inevitable, he tries to think about what conversations would interest him and resonate with the audience.
While hosting a recent episode of his show, O’Connor spoke about Los Angeles Clippers point guard Kris Dunn and his ability to lock down his opponents with strong effort and execution on the defensive end. The rationale for holding this conversation, aside from not having spoken about the Clippers in some time, pertained to the fact that he had just been to a game and observed Dunn’s defense against Orlando Magic forward Franz Wagner. Rather than discussing superstar guard James Harden or the potential return of forward Kawhi Leonard, O’Connor opted to canvass the topic and lean into his inquisitive psyche.
“Sometimes simply finding a topic is about, ‘Well, it’s been a while since we talked about this team,’” O’Connor said. “Naturally, of course, there are some teams you’re talking about more often. Especially as the playoffs approach, those become the teams of higher importance.”
As O’Connor is in his inaugural season covering the NBA for Yahoo Sports, he is focused on appealing to the audience and bringing honest insights and opinions predicated on journalistic integrity. Creativity and ingenuity are at the core of his approach within sports media, and he has also been able to exhibit deft versatility along the way to becoming a credible multiplatform presence in the space. In being granted an ostensible auditory pulpit on which to glean his perspectives twice per week, O’Connor maintains the mindset of a journalist and editorializes with factual evidence to back his claims.
“I think mostly, you’re serving the fan,” O’Connor said. “I think honesty is what matters most. Being honest in your thoughts [and] honest in your opinions on players and teams, and ultimately, you’re doing fans a disservice if you don’t do that.”
In delivering digital content surrounding the personnel and teams in the NBA, O’Connor ensures that he takes part in networking and attends different matchups and league events. Rather than doing all of his work remotely, he is on the road for proceedings such as All-Star Weekend and will hover around the sidelines before a game begins. There are instances where he meets up with sources, but he nonetheless frequently remains in communication with those around the game and values transparency.
“I’m not somebody who’s in the business of trying to newsbreak at all – it’s not a priority for me one bit,” O’Connor said. “It’s obviously good to be in the know, but that comes with developing trust over time and that comes with maintaining a friendship, relationship – whatever you want to call it – with those people over the course of time.”
O’Connor never thought he was going to leave his job at The Ringer writing and podcasting about the NBA, and he ostensibly rendered himself a pillar of the startup company. Having the chance to work under the leadership of founder Bill Simmons and other experienced reporters, he envisioned himself continuing to grow with the brand and becoming immersed as a podcast host.
Over his eight years with the company, O’Connor gained eminence and prestige in the sports media landscape, and Yahoo Sports made it known that there was interest in his services. Meeting with Yahoo Sports president Ryan Spoon and head of content Sam Farber, along with other leadership at the company, helped convince him to make the move.
“Sam and Ryan just have a vision for me and for the company as a whole that just spoke to me in ways that I’m really, really excited about,” O’Connor said, “and plus the opportunity to host my own show, and to do that twice a week for Yahoo right now allows me to talk to different types of people and have certain conversations that I really want to have about the NBA [and] talk to players. And I think right now, we’re still in the early phases of that, but I’m very excited about the way we’re going to build out my show in the months and the years to come with Yahoo.”
Over the last several months, Yahoo Sports has expanded the scope of its sports media coverage through adding established professionals across several areas of focus. Before O’Connor signed on to join the brand, the outlet welcomed Ariel Helwani, Damien Harris, Nate Tice and Russell Dorsey among others to contribute their expertise and showcase their fluency in respective niches. In the end, the means by which O’Connor envisioned his career evolving matched with the intent expressed by Yahoo Sports of establishing and building out his own show.
“I like the way it looked, I love their social presence and now being part of it, getting to call it, ‘Our social presence, our videos,’ it’s been really nice working with the team and making some of that stuff – the ideas that we have – into a reality,” O’Connor elocuted. “It’s still early – I think it’s going to get even better in the years to come.”
As someone who focused on writing early in his career and later added podcast hosting to his repertoire, O’Connor understands the importance of a multiplatform distribution strategy. Situated within a fractionalized media landscape, he does not discern significant overlap in the audience across different verticals. On the contrary, he feels that consumers will remain loyal to the outlets towards which they are most comfortable. Because of this empirical proclivity, it is incumbent on O’Connor and Yahoo Sports to meet the consumers where they are and create informative, compelling content.
“A lot of people, they might just watch podcasts on YouTube and they might not even have Spotify downloaded on their phone, and they might never read anything,” O’Connor hypothesized. “They might just watch YouTube, and there might be people who only scroll X all day, and they otherwise may never discover that you have a podcast, but they might see that 15-minute clip you put out talking just simply about the Pelicans.”
Over the years, various studies have demonstrated a diminished aggregate attention span, subsequently leading brands to emphasize the creation of short-form content catering to these trends. Yet O’Connor grew up reading in-depth stories on Grantland and subsequently thrived in the space, producing a yearly NBA Draft Guide that accumulated plaudits and feedback from industry professionals. Even so, he feels there is still a large market for longform podcasts; however, they are oftentimes supplemented by other content strategically created and placed in other domains.
“If I record a 90-minute sitdown interview with LeBron James, there’s going to be a large chunk of people who watch that entire 90-minute interview, but then there’s going to be probably even a larger chunk of people that are only going to see the one-minute clip on TikTok, the three-minute clip that I put out on X, the 20-second clip that someone clipped themselves and posted on Instagram Reels,” O’Connor explained. “So I think the short form content is massive in its own way, but so often, short form content is cut from that longform piece of content.”
When O’Connor was a college student studying psychology and communications at Bridgewater State University, he landed an internship with NBC Sports Boston and excelled at the regional sports network. Writing for SB Nation within its CelticsBlog, he began to discover his lane in the content sphere and demonstrated an unwavering work ethic in the venture.
Even though he did not have the confidence to join an upstart venture such as The Ringer when it was founded in 2016, he gave it a shot since the opportunity was available. O’Connor was hired because the company liked his NBA Draft Guide that he had been producing independently and wanted him to bring it to the outlet. Later in the year, they had him appear on a podcast with Chris Vernon, which eventually turned into an eight-year partnership.
“I don’t think I really did any podcasting prior to The Ringer, now that I just think about it off the top of my head,” O’Connor said. “I think that was really the first podcasting I had ever done.”
O’Connor rapidly became comfortable discussing basketball in the podcast setting, but he learned more about hosting through watching Vernon in particular. Being able to work alongside someone with two decades of radio experience was fortuitous, witnessing the preparation, foresight and aptitude required to effectively guide a program and the topics it covers.
Through his first few months with Yahoo Sports, O’Connor has welcomed a variety of colleagues onto his program in a guest rotation, including Adam Mares, Tate Frazier, Dan Titus and Tom Haberstroh. There is no specific co-host that is affixed to the show, and O’Connor is still trying to determine the people with whom he has rapport and synergy, intangible characteristics that can be bolstered through repetition.
“I kind of look at it right now as its extended preseason in some ways where it’s figuring out who’s going to be that rotation over the course of time,” O’Connor said. “Who are the people that I really enjoy talking to where I feel like there’s a natural chemistry? People who aren’t afraid to disagree with me or call me out if they say something that I think is stupid.”
Since O’Connor is giving his opinions about basketball, he has been subjected to criticism and backlash for some of his takes over the years. While he has relationships with people who are within the fabric of the league and connected to the news cycle, he safeguards against investing his time into those who are duplicitous or not able to exercise mutual benefit. In previous years, an agent liked O’Connor because he spoke positively about one of his clients. When O’Connor was critical of another client years later, the agent communicated his displeasure using an expletive and ultimately stopped talking to him.
“If that person did that to a 21-year-old kid right out of college, that person might be influenced by that,” O’Connor surmised. “Like, ‘Oh no, no, I didn’t mean it,’ but again, you need to be honest to the fans, and that means being honest with your own thoughts and opinions.”
According to a recent report from Acast, 38% of podcast listeners plan to increase time consuming on-demand audio in the next six months. This same research also divulges that 72% of respondents have watched a video podcast. As O’Connor considers the future of his multiplatform endeavor, he hopes to have more conversations with players, coaches and executives, giving listeners access to the inner workings of the sport. Through deliberation, debate and discourse, he seeks to advance stories on the program.
“Podcasts are edited at a very high level on the video side of things, [and] the social stuff is very impressive,” O’Connor said. “My editor, Matt Wong on the NBA side of things, he’s been great to work with on the editorial side, so I’ve been very impressed with the team that’s already been assembled by leadership with Sam Farber and Ryan Spoon and working with them so far. It’s only been – what, it’s December right now – it’s been about two full months. It’s exceeded my expectations for sure so far.”
Within his new role, O’Connor has a consistent multiplatform presence with Yahoo Sports and has been blown away during his early time with the company. Viewing its social media pages, he was amazed at the three-minute turnaround of learning news, creating a graphic and posting everything online. O’Connor has observed that things move quickly at the company, and he has thoroughly enjoyed working with colleagues in production, editorial and management. Through the whirlwind of the offseason and familiarizing himself with Yahoo Sports, O’Connor looks forward to a bright future replete with innovation in digital media and continued proliferation of basketball.
“I never dreamed of being able to have this career in sports media,” O’Connor expressed. “I didn’t think it was possible. It always felt distant, and so the fact that I’m in it is something that I don’t ever take for granted. So it’s always about continuing to try to do your best because I love what I do and I would never want to give it up.”
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Derek Futterman is an associate editor and sports media reporter for Barrett Media. Additionally, he has worked in a broad array of roles in multimedia production – including on live game broadcasts and audiovisual platforms – and in digital content development and management. He previously interned for Paramount within Showtime Networks, wrote for the Long Island Herald and served as lead sports producer at NY2C. To get in touch, email Derek@BarrettMedia.com or find him on X @derekfutterman.
