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Bruce Gilbert Is Still Learning

“The minute I stop learning is the minute I should stop doing this job. I think there’s always something to learn and that’s never been more true now.”

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A lot of ego exists in sports radio. Many people in the business have inflated opinions of themselves. Bruce Gilbert is not one of these people. He’s one of the most humble individuals you’ll ever meet in the industry.

Bruce could walk around like a peacock as the Westwood One/Cumulus Media Sports SVP and the guy who once hired Colin Cowherd at ESPN. But Bruce still resembles the younger version of himself that was elated to call high school hockey games in Wisconsin for 25 bucks a pop.

The tie-in with hockey makes a lot of sense because Bruce truly does resemble a hockey player. He’s an incredibly hard worker, but when it comes time to receive accolades, he’d rather put his head down as if to say, “I can’t achieve anything without my teammates.” Maybe it’s his Midwestern roots as a kid born in a little town north of Champaign, Illinois. Maybe it’s because Bruce is simply a genuine dude who gets respect because he shows respect.

Bruce is one of the brightest programming minds the business has ever seen. He hasn’t just randomly stumbled onto success; the guy knows what he’s doing. When Bruce talks about what he looks for in a host and stresses the importance of attending conferences like the upcoming BSM Summit, there are a lot of people that can benefit from his views.

We also chat about what the sports radio industry does best and worst, as well as what Bruce would change about his career. Enjoy!

Brian Noe: When in your life did you think, hey, sports radio might be what I want to get into?

Bruce Gilbert: Well, I’m so old, Brian, that there was no sports radio when I decided I wanted to get into radio. My dad was in the radio business. I had great parents and a great dad. He would let me come to the radio station. Every radio station he worked at was just magic to me. From the equipment to the announcers to just the activity and the buzz in the building.

I think I was probably about five years old when I was like, this is what I’m doing. I wanted to be a disc jockey, man. I wanted to play records and talk up the intros and be a disc jockey. To me it was like, you get paid for this? You got to be kidding me. I had a destiny that started at a pretty young age.

BN: What was your first radio gig?

BG: My dad was the general manager of a radio station in Binghamton, New York. WNBF. It’s still there. It’s a news talk station. It was owned by Stoner Broadcasting at the time. They were the flagship station for the Binghamton Broome Dusters, which was the minor league hockey team that played there. My first job was board-oping Binghamton Broome Dusters games at the age of 14. I think I was in the 7th or 8th grade.

I prayed that the game would go really fast because if it got over between 9:30 and 10, I got to play a few songs before the network news at the top of the hour. That was my dream. It turns out it’s funny, I ended up in sports radio; I started in sports and ended up in sports. It was awesome. It was the coolest thing ever to be able to do that.

BN: What led to you being on the programming side of the business?

BG: That’s just what I fell in love with. It was probably at that time, being a teenager, it was about the music and listening to music radio. In that part of the country, we were all influenced by legendary radio station WLS. WLS was in 50 states, a huge 50,000-watt Clear Channel AM radio station that played top 40 music. We all wanted to be big-time disc jockeys on WLS.

I think the other thing is my dad was in sales and it just didn’t seem as sexy. Even though he tried to tell me and he was right, he’s like don’t you see all the sales people drive the really nice cars and all the disc jockeys drive the really shitty cars? [Laughs] And I said I don’t care, I want to be on the air. That’s what I want to do. That’s where it all came from.

BN: When you’re evaluating a sports radio talent, what are you looking for and what are you drawn to?

BG: I know this sounds like the cliché answer, but the number one thing I’m looking for is authenticity. With authenticity, I think I would add to that you’ve got to be real, you’ve got to be self-deprecating, but you also have to have a life. By authenticity, it’s not just being authentic in your sports opinions, like I’m going to be authentic in what I think about that coach or that player. You have to be authentic about how you live, where you go, who you talk to, what you’re into, what movies you watch, what television shows you binge, what motivates you, what aggravates you, and all those things.

I guess what I look for, it’s one thing to be authentic, it’s another thing to be openly authentic. I’ve often said that the greatest talk show hosts, regardless of what they’re talking about, are willing to basically perform open heart surgery on themselves every day. I’m going to open it up and just throw it out here. I’m not going to apologize for it because that’s what’s in my gut. That’s what’s in my heart. That’s what’s in my soul.

You can get away with a fake persona or an over-the-top personality that you create that is some sort of alter ego for a little while, but it’s not sustainable in the long run. The only thing that’s sustainable is being you.

BN: When you look at the sports radio industry as a whole, what do you think is working well and what do you think should be a lot better than it currently is?

BG: What’s always worked well, when done right, when sports radio is done effectively and in a compelling and engaging and authentic way, it’s the ultimate escape. We’ve seen that again during these incredibly odd times we’ve been living in, now going on two years.

Like every radio station, we had a dip at the beginning of the pandemic. As sports came back, so did sports radio; 2021 was a really good year for the sports format. I think it’s because people got burned out on all of the negativity and the depressing news stories that were repeating themselves over and over. On top of it, how everything became politicized and the country got more and more divisive.

The only true uniting thing was sports. Sports unites us all. It unites people and galvanizes people in a really tight-knit community kind of way. You and I may be polar opposite politically, but if we end up sitting next to each other at the game and we’re both rooting for the same team, I don’t care what your politics are, I’m high-fiving you when we score a goal, or we get a touchdown, or we hit a home run.

That is what sports radio does best. When it’s in its prime and it sticks to the fun of the games and the storylines of the real-life heroes and villains in sports, it’s the perfect escape from all the madness of life. That’s the positive. I don’t see that ever not being a positive in a really true way. That’s motivating to me and what I love about this format.

Now how did you phrase that; what are we not doing well?

BN: Right, yeah, what isn’t where it needs to be currently?

BG: I know it sounds like I’m programmed to say this and it’s the hip, cool thing to say and everybody’s woke and all that stuff, but sports radio is way too old and way too white in general.

Look, there are people that are doing a great job of bringing in new voices from different backgrounds, but I think it’s problematic. Especially when you look at television sports and how much better they’ve done with female anchors, female reporters, female play-by-play announcers, and we’re just behind.

I think it’s a product of not digging deeper or going wider. It’s also a product of radio maybe not paying as well as television, radio maybe not being as sexy as it once was. But those are just excuses, right? If you look at the audience of the marketplace and you look at the demographics and the ethnic backgrounds of those that participate in America’s most popular sports, I don’t think sports radio is close to being reflective of those constituencies.

It’s incumbent upon those of us that are in this format to make that happen. It is true you want the best person for every open job, but you also just can’t keep recycling the same people over and over. You’ve got to go give some new people a chance. They’re going to have to stumble a little bit and figure their way through it, but if they have the right support, it will make the format more relevant and I think give the format more life moving forward.

BN: The word escape stands out to me. When sports radio dips into a political issue, it can be an interesting conversation, but it becomes less of an escape. Where do you stand on that dilemma?

BG: Yeah, it’s a great point. We’ve had a lot of conversations internally about how to address that. My personal opinion — and this is based heavily on watching how those things impact research and ratings — is that we can’t be an escape if we go down the political path. Sports radio is most successful when it’s apolitical because being apolitical is one of its true positives. That’s the uniting part. The minute we get political, we’re not uniting anymore, we’re divisive.

As much as you want to be authentic and you want to talk about what people are talking about, I think my experience is saying, and what I’ve seen as I’ve watched it unfold, I would say it’s a mistake to get political or go into those areas that could be perceived as political. We have a small audience to begin with. It’s a niche format. Why do you want to alienate part of that audience by taking one side or the other on a political issue that’s going to actually run people off?

BN: With the BSM Summit coming up, why is it important to be there?

BG: Well, first of all, we all miss each other, right? None of us have been able to see each other because we haven’t been able to travel for a couple of years, and a lot of us know each other and go back a lot of years. There’s a real value in just being able to connect with people.

The side effect of being able to connect with people is I think you learn in those situations that some of the things that you see as obstacles or problems that you’re dealing with, it’s really healthy to talk to other people that are going through the same thing and realizing, oh, I’m not alone in this. They’re having to get over that hump as well. It works in the reverse in a positive way. You see somebody that has come up with a solution or done something unique, that becomes contagious and that drives us forward.

The other reason I think it’s important is because when somebody like Jason takes the time and makes the effort to pull all those people together, and he works his ass off on this thing, I just really respect that. That is a strong message from a person that this is worth our time and worth getting away for a couple of days and shutting ourselves in a room and trying to make it better.

One of the problems with any business, I think, is complacency. If we don’t sit down in a place like that and be honest with each other about what our challenges are and how to address them, then we’re going to become complacent. I think what Jason’s done really well is he’s made it a point to not allow it to be a place where we all just sit around and pat each other on the back and talk about how great we are or live in the past. He’s done a really good job of making it about the now and going forward.

I look forward to that because look, I’ve been doing this a long time; the minute I stop learning is the minute I should stop doing this job. I think there’s always something to learn and that’s never been more true now when you look at video platforms, all the different digital platforms, how to get your things out on social media, the algorithms, all the different things that we never had to deal with that we now need to deal with. You can’t deal with it if you aren’t willing to learn it and understand it and grow.

That’s why I think it’s critical. I think it’s even more critical because of the work that Jason puts in. It’s not just a hey, let’s get together and scratch each other. It’s let’s really, really make this worth our time.

BN: What’s something valuable that you’ve taken away from the Summit before?

BG: I get two really critical things out of Jason’s Summit in particular. One, a lot of affirmation. You’re always experimenting and trying new things. It might be one little thing that you’re doing in one little market and you wonder if that’s the right thing. Then you go there and you hear somebody talk about something similar or maybe even something exactly the same and you’re like, okay, good, I respect that person and that person is trying the same thing or thinks that’s a good idea. There’s an affirmation aspect to it.

The second thing that I always get out of it is just motivation. What comes out in two days with a group of people like that is that most of us aren’t in this for the paycheck — although we all like to get paid — but we’re in it because it’s a passion. I think about outside of my wife and kids, my two loves in life are sports and radio. I get to do them both every day. What happens is you see that passion come out in different ways. Not all of them that are there are radio people specifically. They may be in a tangential business, but that passion is overwhelmingly motivating to me and I find myself recharged, re-energized.

I think affirmation, motivation, and sometimes those two actually drive you to try something that maybe you’ve been thinking about. I know I’ve had this happen where I’ve been thinking about something for maybe years and you go to a conference like that and you’re like, why the hell haven’t I done that? Now I’m going to because I keep putting it off, and if so-and-so can do it, or so-and-so believes it’s a good idea, then I’m going to go forward.

BN: What’s the most gratifying aspect of your job?

BG: That’s easy: Watching other people succeed. When I see someone who I know is busting their ass or has been trying to get something to work for so long and it clicks and it happens, or the ratings finally happen, I totally am driven by that. I love seeing it.

Those are the people I then absolutely want to help as much as I can. By help, I mean help their career, help them grow, help them find the next job or whatever they want to do that’s important to them. That, to me, it’s all about that. It’s about watching people win that really deserve it and earned it.

BN: What’s the most difficult part of your job?

BG: I don’t dwell on the bad stuff but certainly over the past couple of years, the most difficult thing has had to be downsizing our teams. Everybody has been through it, but that doesn’t make it okay. Nobody ever deserves to lose their job, especially if they love what they do. But everybody can’t keep their job. It’s just not realistic. It’s not how it works.

You’ve experienced it yourself, unfortunately, and you’re an extremely talented talk show host that I think is remarkably bright and unique. So if guys like you can lose your job, it can happen to anybody.

I have to admit, I’ve met a couple of people in my career that actually enjoy firing people and I’m telling you those people are either the devil or they’re just not human. There is nothing fun at all about having to tell people that their position no longer exists. It absolutely blows. That’s the worst by far.

BN: Yeah, absolutely. That’s crazy; I can’t imagine someone enjoying that.

BG: There are some people that do. They’re proud of it. It’s like something’s wrong with you. [Laughs]

BN: Put your current job to the side, it doesn’t count toward this question. What’s the most fun you’ve ever had during your career?

BG: Maybe this is nostalgic and we romanticize things, but probably when I was working at my dad’s Wisconsin-owned radio station. I think when I had the most fun was doing play-by-play. I used to do high school basketball and high school hockey, believe it or not. I loved it, man. I thought it was the greatest thing ever. The hockey games were outdoors. I was standing in a snowbank with a headset on calling a high school hockey game, freezing my everything off.

I think about those times and I’m like, that was a freakin’ blast, man. It was so much fun. I’m sure I had some worries, but I don’t remember having a single worry in the world then. I didn’t have a family to support yet, so it was just like, make your 25 bucks doing play-by-play and go through the McDonald’s drive-thru and life is good.

BN: [Laughs] Totally, man. For you personally, do you look to the future as far as goals or are you an in-the-now type of guy?

BG: I think for me personally, I’m definitely a here-and-now person. That’s how I was brought up. That’s my Midwest upbringing. My parents were like, as long as you’re getting a paycheck from somebody, you give them 150%. You get up in the morning, you bust your ass and go to work for them, and you do everything to make them look good and smart and make them money. If something else happens to come along, then you consider it.

That’s the reason I say I’ve been very lucky. I’ve had a lot of things just organically come my way. I don’t know why or how I was lucky enough to fall into those places. I guess a lot of really good people that have helped me and looked out for me, mentors of mine.

But yeah, I don’t get fixated personally. There’s no guarantee. For me personally, I’m all about today being as great as it can be and tomorrow being whatever it’s going to be.

BN: If you could change anything about your career, would you?

BG: No. Not at all. And that doesn’t mean that I don’t think I’ve made some mistakes. I absolutely have made some mistakes. I think I made them with good intentions. Even when I made the wrong step, it all made sense when I did it. That’s not because I’m smart or I did everything right because like I said, I’ve made some mistakes.

But just because you make mistakes doesn’t mean you have to have regrets. I don’t regret it. All of those things get you where you’re at now, good and bad. I’ve made some mistakes, but I wouldn’t change anything. I’ve been extremely lucky, man. Extremely lucky.

Barrett Blogs

Would Local Radio Benefit From Hosting An Annual Upfront?

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How many times have you heard this sentence uttered at conferences or in one of the trades; radio has to do a better job of telling its story. Sounds reasonable enough right? After all, your brands and companies stand a better chance of being more consumed and invested in the more that others know about them.

But what specifically about your brand’s story matters to those listening or spending money on it? Which outlets are you supposed to share that news with to grow your listenership and advertising? And who is telling the story? Is it someone who works for your company and has a motive to advance a professional agenda, or someone who’s independent and may point out a few holes in your strategy, execution, and results?

As professionals working in the media business, we’re supposed to be experts in the field of communications. But are we? We’re good at relaying news when it makes us look good or highlights a competitor coming up short. How do we respond though when the story isn’t told the we want it to? Better yet, how many times do sports/news talk brands relay information that isn’t tied to quarterly ratings, revenue or a new contract being signed? We like to celebrate the numbers that matter to us and our teams, but we don’t spend much time thinking about if those numbers matter to the right groups – the audience and the advertisers.

Having covered the sports and news media business for the past seven years, and published nearly eighteen thousand pieces of content, you’d be stunned if you saw how many nuggets of information get sent to us from industry folks looking for publicity vs. having to chase people down for details or read things on social media or listen to or watch shows to promote relevant material. Spoiler alert, most of what we produce comes from digging. There are a handful of outlets and PR folks who are great, and five or six PD’s who do an excellent job consistently promoting news or cool things associated with their brands and people. Some talent are good too at sharing content or tips that our website may have an interest in.

Whether I give the green light to publish the material or not, I appreciate that folks look for ways to keep their brands and shows on everyone’s radar. Brand leaders and marketing directors should be battling daily in my opinion for recognition anywhere and everywhere it’s available. If nobody is talking about your brand then you have to give them a reason to.

I’m writing this column today because I just spent a day in New York City at the Disney Upfront, which was attended by a few thousand advertising professionals. Though I’d have preferred a greater focus on ESPN than what was offered, I understand that a company the size of Disney with so many rich content offerings is going to have to condense things or they’d literally need a full week of Upfronts to cover it all. They’re also trying to reach buyers and advertising professionals who have interests in more than just sports.

What stood out to me while I was in attendance was how much detail went into putting on a show to inform, entertain, and engage advertising professionals. Disney understands the value of telling its story to the right crowd, and they rolled out the heavy hitters for it. There was a strong mix of stars, executives, promotion of upcoming shows, breaking news about network deals, access to the people responsible for bringing advertising to life, and of course, free drinks. It was easy for everyone in the room to gain an understanding of the company’s culture, vision, success, and plans to capture more market share.

As I sat in my seat, I wondered ‘why doesn’t radio do this on a local level‘? I’m not talking about entertaining clients in a suite, having a business dinner for a small group of clients or inviting business owners and agency reps to the office for a rollout of forthcoming plans. I’m talking about creating an annual event that showcases the power of a cluster, the stars who are connected to the company’s various brands, unveiling new shows, promotions and deals, and using the event as a driver to attract more business.

Too often I see our industry rely on things that have worked in the past. We assume that if it worked before there’s no need to reinvent the wheel for the client. Sometimes that’s even true. Maybe the advertiser likes to keep things simple and communicate by phone, email or in-person lunch meetings. Maybe a creative powerpoint presentation is all you need to get them to say yes. If it’s working and you feel that’s the best way forward to close business, continue with that approach. There’s more than one way to reach the finish line.

But I believe that most people like being exposed to fresh ideas, and given a peak behind the curtain. The word ‘new’ excites people. Why do you think Apple introduces a new iPhone each year or two. We lose sight sometimes of how important our brands and people are to those not inside the walls of our offices. We forget that whether a client spends ten thousand or ten million dollars per year with our company, they still like to be entertained. When you allow business people to feel the excitement associated with your brand’s upcoming events, see the presentations on a screen, and hear from and interact with the stars involved in it, you make them feel more special. I think you stand a better chance of closing deals and building stronger relationships that way.

Given that many local clusters have relationships with hotels, theaters, teams, restaurants, etc. there’s no reason you can’t find a central location, and put together an advertiser appreciation day that makes partners feel valued. You don’t have to rent out Pier 36 like Disney or secure the field at a baseball stadium to make a strong impression. We show listeners they’re valued regularly by giving away tickets, cash, fan appreciation parties, etc. and guess what, it works! Yes there are expenses involved putting on events, and no manager wants to hear about spending money without feeling confident they’ll generate a return on investment. That said, taking calculated risks is essential to growing a business. Every day that goes by where you operate with a ‘relying on the past’ mindset, and refuse to invest in growth opportunities, is one that leaves open the door for others to make sure your future is less promising.

There are likely a few examples of groups doing a smaller scaled version of what I’m suggesting. If you’re doing this already, I’d love to hear about it. Hit me up through email at JBarrett@sportsradiopd.com. By and large though, I don’t see a lot of must-see, must-discuss events like this created that lead to a surplus of press, increased relationships, and most importantly, increased sales. Yet it can be done. Judging from some of the feedback I received yesterday talking to people in the room, it makes an impression, and it matters.

I don’t claim to know how many ad agency executives and buyers returned to the office from the Disney Upfront and reached out to sign new advertising deals with the company. What I am confident in is that Disney wouldn’t invest resources in creating this event nor would other national groups like NBC, FOX, CBS, WarnerMedia, etc. if they didn’t feel it was beneficial to their business. Rather than relying on ratings and revenue stories that serve our own interests, maybe we’d help ourselves more by allowing our partners and potential clients to experience what makes our brands special. It works with our listeners, and can work with advertisers too.

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Brandon Kiley Doesn’t Pretend To Be Someone He’s Not

“There was a time where the audience probably said, this guy isn’t a St Louisan. But this is home for me now and I’ve adopted it.”

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There must have been something about Brandon Kiley that everyone saw as a young aspiring sports radio host. Nick Wright saw enough to bring him to Houston at SportsRadio 610 as an intern for a summer. Will Palaszczuk saw enough to urge him to apply for his old job in Columbia, MO at KTGR. Ben Heisler saw enough to know he’d fit perfectly with Carrington Harrison in afternoon drive at 610 Sports in Kansas City. 

Maybe you can chalk it up to Kiley being able to make such great contacts. Or maybe it’s just that he was supremely talented at a young age. Odds are it’s a combination of both. But he was destined to be a sports talk host somewhere, it just turns out he’s having success over the air in a city he never imagined he’d work in. 

A Kansas City kid, Kiley knew at 16 years old he wanted to be a sports radio host. He was even more sure of it when he started doing college radio at Mizzou. But it was in Houston where he got his real taste of what sports radio was like.

“I went to 610 in Houston for the morning show with Nick Wright,” Kiley said. “He basically just assigned me as an extra producer. We had known about each other through Twitter and I had a little bit of a relationship with him beforehand. I think he knew I was willing and able to take on more tasks than a typical intern would usually do. Essentially, I became an extra guest booker, cut audio for them, and came up with topics at night. It was like he had an extra producer for the summer and it was my first real experience doing something like that.”

Imagine the confidence he left Houston with as he traveled back to Columbia for another year of college at Mizzou. Few, if any, on campus could have claimed the kind of summer Kiley just had. He parlayed that experience into a once-a-week show at KCOU, the student radio station. The following semester, he pitched the idea of doing a daily show

“I told them I’d take any time slot available,” Kiley said. “The one that I got was the very glamorous 6-7 am time slot. There weren’t a whole lot of college kids that wanted to wake up that early every morning. I ended up having a rotating cast of co-hosts and it ended up being super valuable because I learned how to work with a lot of types of personalities.”

He excelled as a host and found his style behind the mic, and soon after, he got his first big break. In March of 2014, Will Palaszczuk contacted Kiley and told him he was taking another radio job outside the market. The two knew of each other, seeing as both were in Columbia and covering the same games in town. Palacsuk told Kiley he needed to apply for the spot he was leaving at KTGR.

“There was literally one sports station and one sports show in town and it was that one,” Kiley said. “I applied to him the previous semester and said, hey man, if you guys have anything available I would love to come work there. It just so happened he got a job elsewhere and he called me up and said, ‘Hey man, I don’t know what your plans are, I’m about to take another job and they’re going to post my job available. I don’t know if they’re going to make it a producer or co-host gig, but I think you should apply because I think you’d be good at it’. Will’s good work helped a ton in terms of me landing the gig. I graduated and told them I wanted to make it full-time.I was essentially a producer and co-host for the afternoon show. I never even applied anywhere outside of Columbia”

For two years, Kiley stayed at KTGR and covered the Missouri Tigers. He was fresh out of college and living in a college town doing what he loved in his early 20’s. It wasn’t a bad life. But one night in Columbia changed his entire professional career. It just so happened it occurred on the rooftop at Harpo’s, one of the most well-known establishments in town.

“My roommate at the time, we both worked at the radio station in Columbia,” said Kiley. “He worked at the hit music station and I worked at the sports station. We all went out one night at Harpo’s and he said, ‘Hey, I just want to let you guys know I’m getting out of radio and moving to Kansas City.’ I was like, oh shit, what am I going to do? Our lease was up in two months, so the timing worked out well and I was looking at Barrett Sports Media looking where I could go next.”

“My girlfriend at the time, now my wife, was from St. Louis and there was a job available there. I had always thought, that’s not a place I want to live, why would I ever want to live in St. Louis? They didn’t have a football team, it just didn’t seem like a great fit for me. But my buddy tells me he’s moving and I’m like, St, Louis it is! That night I ended up applying for the job and got a call back from Chris “Hoss” Neupert, who at the time was the PD here, and asked if I would be interviewed with him and Kevin Wheeler, whose show I would be producing.”

So off to St. Louis he goes. For three and a half years, Kiley embraces his new city and tries to work his way up at 101 ESPN. 

But the Kansas City kid felt a pull back to his hometown. Oddly enough, Ben Heisler even reached out to tell him he was leaving the station to pursue another opportunity in sports. It felt like the perfect time to pursue his dream of doing sports radio at the station he grew up listening to.

“I’m from Kansas City and grew up listening to 610 Sports Radio,” Kiley said. “A guy I listened to growing up was Nick Wright. I also listened to a bunch of Carrington Harrison, Danny Parkins and Ben Heisler. Those guys had what I consider one of the best shows in Kansas City sports radio history. I got to know them through Twitter and Heisler sent me a text. He knows I’ve always been interested in moving to KC. He tells me he’s about to get out of radio and into more fantasy football stuff and his job is going to come open.

“I had applied for multiple other jobs in KC over the years and had never gotten any real consideration. When Heisler left, I knew Carrington and thought this might work out. I ended up getting in contact with their PD Steven Spector and it felt like a real opportunity. I got what I considered to be my dream job, producing in the afternoons and hosting a Saturday show at 610 Sports. I thought, what could there be more in life than this? This is the best.”

But life happened and he had to make a decision around three months after moving to Kansas City.

“2-3 months later it became clear, it was going to be difficult for my girlfriend, now wife, to move to Kansas City with all of the family ties she had in St. Louis,” said Kiley. “It was the decision of, do you stay in Kansas City and chase the dream or do we alter the dream, in terms of the job, and see if there’s anything in St. Louis?”

He never thought his best years and most successful years as a sports radio host would come in St. Louis but they have. It’s a city he loves and he’s worked hard in hopes it will love him back. But he’s also not going to pretend to be someone he’s not. Though it can sometimes be hard for St Louisans to accept someone that’s not from there, Kiley doesn’t act like he attended World Series games in 1982, listened to Jack Buck growing up or watched Kurt Warner at the Edward Jones Dome. He’s himself.

“That wasn’t my love and I can’t pretend that it was,” said Kiley. “Have there been times, especially early on where that was a potential issue for me? Yeah it was. There was a time where the audience probably said, this guy isn’t a St Louisan. But this is home for me now and I’ve adopted it. It does in a lot of ways remind me of Kansas City, where if you take the time to know what the soul of the city really is, in terms of sports, I think people can appreciate and respect it.”

Kiley doesn’t hold on to his Kansas City roots on the air, in terms of the topics he talks about. He’s a Chiefs fan and even writes for Arrowhead Pride, but he’s not going to talk a lot about the Chiefs in a city that doesn’t have an NFL team. He’s also a Mizzou grad and talks about the teams on Rock M Nation, but again, he’s rarely, if ever, going to do several segments a day on the Tigers. Instead, he knows the audience wants to hear about the Cardinals. Blues talk is clearly next in line. Everything else falls down the order if not off of it completely. 

Kiley grew up watching baseball, so he can easily break down what issues the Cards’ offense may be having in the middle of May, but hockey was different. He didn’t grow up around the game and the transition to having in-depth conversations on the Blues was a more difficult task. 

“When I came here the first time it was during the middle of a Blues’ playoff run. At that time I was just plopped into this thing, and I didn’t know shit about hockey. I had probably watched about 10 hockey games in my entire life. I’m looking at Kevin Wheeler like, I’ve got to be honest I don’t have a lot on hockey I’m going to be able to help you with. If you could help bring me along with it, that would be great. Over the years I’ve been able to take it in. I used to host a show with Jamie Rivers, who’s a former Blues player. If you told me five years ago I’d be able to do that, much less enjoy doing that, I would have said you’re out of your damn mind.”

Whereas most sports radio shows in football markets are searching for content to help fill segments, this is one of the sweetest times of the year for Kiley and everyone at 101 ESPN. The Blues are deep in the playoffs and the Major League Baseball season is underway. His show BK and Ferrario covers it all every weekday from 11 am – 2 pm. 

Kiley never thought this would be his life, but he loves what he’s built in St.Louis and doesn’t give off the vibe he’s looking to leave anytime soon. He’s a great example of someone who didn’t pigeonhole himself into just one market. He was willing to look outside of his hometown and has found true success. 

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Will Middlebrooks Has Been The Breakout Star Of The Red Sox Season

“If I was going to work for an organization or a regional sports network, why not the Red Sox, for someone that I’m actually a fan of?”

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The Boston Red Sox experience in 2022 is just different. In every way.

The team has struggled out of the gate. They certainly aren’t the team that was two wins away from the World Series last year.

Fenway Park doesn’t even accept cash anymore.

But it’s not just that the Red Sox are different on the field or at the ballpark – they are different on television too.

When loveable, longtime Sox broadcaster Jerry Remy died in October 2021 at the age of 68, we knew that consuming the Red Sox on TV would never be the same.

There is no replacing Jerry Remy. One person can’t do it. No way.

And the fans know it.

The bosses at the NESN know it too. They haven’t tried to replace Remy on the broadcasts with just one person. 

In fact, they’ve brought in several new people to the broadcast team. A group of people just rotating in, giving viewers a different experience and a different perspective every night. 

They’ve added former Red Sox players Kevin Youkilis and Kevin Millar to the broadcast booth roster. They’ve added Tony Massarotti of 98.5 The Sports Hub as well.

And in the pre- and post-game studio, they’ve taken a similar approach, which is an extension of previous years, mixing and matching host Tom Caron with a slew of former Red Sox players including Jim Rice, Tim Wakefield, Ellis Burks, Lenny DiNardo, and former Sox infielder Will Middlebrooks, who will be in the studio for about 40 games this season.

I think that NESN has found a formula that works. It’s been fun and informative – and different. In a year that serves as a constant reminder of what’s been lost as a viewer, it’s refreshing to realize that these broadcast teams are giving you something gained.

A star is born.

When I mentioned to Caron that I wanted to write a piece on Middlebrooks, he said: “He’s a rising star.”

And it’s easy to see why he feels that way.

Will Middlebrooks is young (33), accessible, opinionated, active on social media, and he has the playing resume to legitimize his point of view.

But it took some real coaxing to get into the business in the first place. After a devastating leg injury ended his playing career in 2019, Middlebrooks was unhappy.

“I sat around and sulked and was angry about it for about three months,” he said. “And my wife, Jenny (Dell), finally said, ‘You need to get off your butt and do something, find not just, work, but find something you’re passionate about again.’”

He didn’t know at that time that he was passionate about media work, but Dell, who works for CBS Sports, volunteered him to do a show at CBS Sports HQ in Ft. Lauderdale, near where their family resides.

“She said, like it or not, you have a show in three days. You’re going to try it out, and if you’re good at it, they’re going to hire you,” he recounts of their conversation. “I was like, I don’t want to do it. I’m not ready to talk about baseball. I hate baseball right now. I just have such a bad taste in my mouth from everything that happened over the past year.”

But that didn’t deter Dell from pushing her husband to take the chance.

“She said, well, I don’t care. I already told them that said you would do it,” he says. “So she kind of threw me to the wolves, but for the best. And I went in and I gritted my teeth and just got it done and then talked baseball. I did it a couple of more times and they said, ‘Hey, you’re decent at this. We’re going to hire you on for a year!” “And here we are, I’m four years into it,” he joked.

And over those four years, Middlebrooks has ballooned into one of the most recognizable follows for baseball fans. In addition to working at NESN and CBS Sports, he’s also one-half of the Wake and Rake podcast, has appeared on ESPN Radio, has done color commentary for college baseball, and has more than 155,000 Twitter followers.

Resonating with Boston 

When I ask Middlebrooks about landing the NESN gig for 2022, he beams through the phone. He says he wanted the challenge of working in Boston and he welcomed the opportunity to expand his media footprint.

It’s evident that he loves the Red Sox – and the city of Boston. How couldn’t he? He made his Major League debut with the organization, played parts of three seasons with the team, won a World Series with the Sox, and met his wife in the city.

“If I was going to work for an organization or a regional sports network, why not the Red Sox, for someone that I’m actually a fan of?” he said. 

While it’s clear that Will loves Boston, and it’s clear why NESN loves him, what needs more unpacking is the attachment that the Red Sox fans have to him considering he spent just those three seasons there and doesn’t live in New England full-time. 

Middlebrooks can’t quite figure out why the people of the region hold him so close, but he does have a good hypothesis.

“I think that if I left anything, it was people saying, ‘well, he played hard. He gave everything he had,’ he said. “And I know that’s really important in Boston, just the blue-collar mentality of ‘keep your head down, work, play as hard as you can, even if things aren’t going well, just bust your butt and be a good teammate and all that.’”

But there just may be something else at play.

“I think a lot maybe had to do with when the marathon bombings (2013) happened…I’m pretty outspoken on social media about that stuff and with my teammates, we all rallied around each other,” he said. “I think I was just lucky enough to be a part of a team that was really special to everybody in Boston. So they embraced me after that.”

The Family Dynamic 

Dell has been in sports media for more than a decade as a host and sideline reporter for CBS and NESN before that. She knows the business and its nuances. She understands when and how to look at the camera and when and how to ask questions of athletes. She knows the expectations of her husband’s current employers. She’s undoubtedly a great resource to have.

But as Middlebrooks finds his own footing in the business, and as his star grows, what is that dynamic like? She has the answers to the tests already, but how does he balance using that resource versus figuring things out on his own?

“I’m very open to anything she has to say,” he said. “I’ll come out of my office, like, ‘Hey, that was pretty good!’ And she’s like, ‘Yeah, it was good…but…”

“She always has something, and at first it used to really annoy me, because I’m like, man, I thought I was doing really good,” he said. “And she’s like, ‘No, you are doing good. I’m just trying to help you get to that next level. There are just little things here and there that you don’t know.’ And as a competitor, it’s really frustrating. But you know, after a couple of minutes I walk away, I’m like, you know what? I’m really appreciative to have that access to someone that can help.”

What’s Next?

At such a young age with such already vast experiences, it seems plausible that even bigger media steps could be in play for the former infielder. I asked him if he has a goal he’s working towards. Sunday Night Baseball? The MLB Network? Something else?

“One thing I’ve really learned is to not look too far down the road and kind of just live in the moment and enjoy the moment,” he said. “I’m really happy with being with with CBS and with NESN, and within that umbrella, of course, I would like to grow. Does that mean in the booth? Does that mean more games pre and post? Sure I’m up for anything where they want me, because what I’m doing right now, I feel like is a dream job outside of playing and I’m so happy with it.”

Middlebrooks has been on the NESN broadcasts all week and will continue through this weekend as the Red Sox host the Mariners in a four-game series.

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