Glenn Ordway Reveals Why He Came Out of Retirement To Launch ‘The Big O Podcast’

Retirement is both a blessing and a curse. It's a blessing because years of hard work and sacrifice allow a person to live life however they want after a certain point. It's a curse because finding ways to keep the days busy can be challenging. For Glenn Ordway , after nearly five decades in radio, it was time to retire from his role at Boston's WEEI four years ago. However, as time passed, his passion for sharing his thoughts with an audience re-emerged.

"The success I had in the [sports radio] business allowed me to live a pretty comfortable life. But to be honest, I just got bored [in retirement]," said Ordway. "It got to a point where you wake up on a Tuesday and ask, 'Do I want to play golf today?' Then you wake up Wednesday, and it's Groundhog Day with the same deal all over again. I needed something to do."

Just over a month ago, Ordway returned to the microphone. This time, he wasn't in Boston or even on terrestrial radio. Instead, he launched a podcast available in both audio and video formats on YouTube. The veteran Boston sports radio voice debuted The Big O Podcast , featuring stories, personalities and interviews from his legendary run at WEEI.

Although Ordway joked in his opening episode about being late to the podcasting party, the results have spoken for themselves. With more than 3,500 subscribers on YouTube alone and several episodes already released, Ordway has built a digital community rooted in storytelling. He's pulling back the curtain on some of Boston's biggest sports radio questions and most controversial moments.

"I've been in the business for fifty years and have been around some great sports teams, memories and personalities. Why not just go back and reconnect with all these moments and people?" explained Ordway. "But I was looking for what could get me the best kickstart out of the gate. There are so many unanswered questions regarding WEEI. I get those all the time. So, why not start with what happened with WEEI?"

The concept for The Big O Podcast began three years ago, after Ordway spent some time enjoying retirement through travel and time with family. However, two hip surgeries, including one that left him completely immobilized, forced him to delay the project several times.

After recovering, Ordway got healthy and lost a significant amount of weight. Eventually, he reached a point where he could begin the early stages of preparing the podcast for launch. Now, just over a month into the project, he says the response has been overwhelming. It has also created monetization opportunities he didn't have more than a decade ago during his first foray into podcasting.

"We've already been hit now by ad agencies that have contacted us with some opportunities. I heard that after the first week, which is amazing. I thought it would take at least six months," said Ordway. "Listeners want to go behind the curtain and know why certain things happened. Radio has trouble doing that because of sponsorships and people who could be affected by it."

Encouraged by the early success, Ordway has begun treating his podcast less like a side project and more like a business. He has plans to expand the operation immediately and into 2027.

"I'm into current sports. Now, I'm into college football because I have a lot of free time to watch it. So, we're going to do more sports stuff and spin it off into another channel," noted Ordway. "Also, two episodes per week will be [Boston] Celtics-related, featuring me, my son and a rotating third person from Celtics media or a former player. But I have other interests, too. In January, I hope to launch a podcast surrounding wine. The idea is to be a regular Joe who sells you on certain wines to try and enjoy."

Since retiring, Ordway has found himself consuming more podcasts than traditional sports radio. He listens not only to research best practices for commercial insertion and content development but also because he finds podcasts more relaxing and appreciates the room they give conversations to breathe.

Drawing from his research and enjoyment of several podcast categories, Ordway has taken a similar approach to The Big O Podcast that served him well for so many years at WEEI. He embraces an unfiltered style of discussion and storytelling that invites listeners into the personalities behind the content.

"I'm willing to talk about anything. In the business, there are certain things you just can't say that you want to. Back then, we were open about the behind-the-scenes aspects of the show and station because it was good fodder for the program," said Ordway. "I'm not taking anything to my grave."

As he revisits his days at WEEI, Ordway has held court with several of the station's current and former personalities, walking listeners down memory lane. He's sat down with Christian Fauria and Lou Merloni, as well as John Dennis, Kirk Minihane and Gerry Callahan. Those three separate conversations also led to an opportunity to reunite the popular Boston trio for an exclusive episode in the coming month.

Ordway maintains a list of potential guests, with each name accompanied by a page of stories he remembers. The notes help him prepare for each conversation. However, despite having a lengthy list of people he wants to interview, he recognizes that not everyone will agree to appear.

"I would love to have Rick Pitino on the program. Rick and I had a small conflict where I denied a request for him to appear on my show when he was at Boston University. Then, when he got the job with the Boston Celtics, good old Rick didn't forget that Ordway stiffed him back then," explained Ordway. "I don't want to just put people on that I've had great relationships with. I'd also like to put some on who I've had a terrible time with and reconcile before we find the eternal dirt nap. I'm trying to bring peace to the world."

Although Ordway still splits his time between his homes in Arizona and Boston, his perspective on Boston sports radio has evolved. He continues to listen to both major stations in the market, but he now follows their content primarily through social media clips rather than extended listening sessions.

For someone who was a giant of the format in Boston, Ordway has noticed significant changes in sports radio since stepping away.

"I made the mistake that a lot of others make when you're entrenched in it. When you have twenty hours of time to fill, you need to find every scab off a topic to extend it. Sometimes that can wear on an audience by trying too hard to find a negative," said Ordway. "No offense to anyone doing it. But in today's sports talk radio, there are more fake or pushed hot takes than ever before. There are people killing themselves to find a hot take, draw it out and throw it on the radio. But that's part of the business. It always has been."

Ordway sees a significant difference between hot-take radio and being unpredictable. He believes that sense of unpredictability is missing from today's sports radio landscape. He also says companies have changed how they define success. Whereas Nielsen ratings once served as the primary measuring stick, success now revolves more around protecting revenue and controlling expenses.

In retirement, Ordway says he doesn't have many regrets. However, he admits one of his biggest is failing to recognize the importance of building his own brand. It was an opportunity he didn't fully appreciate years ago.

"In 2009, when I was negotiating a new deal with WEEI, I had a group that came to me and offered me a deal to become my own brand. It was the group that put together the Dan Patrick Show," explained Ordway. "They wanted me to do a national show and a local show. But it was based on building my brand, not a radio station. If you have a pretty good brand already, spread it out now in digital media. Dan Patrick created a monster of a media operation. Best branding I've ever seen, and one of the greatest regrets of my life was not following Dan's lead. It was a huge mistake."

Ordway may regret passing up the opportunity to build his own brand nearly two decades ago, but he now has another chance to do so on his own terms. With decades of stories to tell, relationships to revisit and a growing audience eager to hear what happened behind the scenes at WEEI, The Big O Podcast has given him a renewed sense of purpose in retirement.

After nearly 50 years in radio, Ordway has learned that stepping away from the microphone doesn't necessarily mean walking away from the business.

"I'm getting back to my old roots, and I'm enjoying it immensely," said Ordway. "Hopefully that comes through to the audience willing to reconnect with an old friend."

Sometimes, all it takes is a little time away to rediscover what made you love something in the first place. If the early returns are any indication, the best chapters of Ordway's broadcasting career may still be ahead of him.

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