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The Business Won’t Run Orlando Alzugaray Over

“Everybody wants to play radio. A lot of us can play radio, a lot of us have an opinion, but do you understand the business?”

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Orlando Alzugaray is a longtime Miami sports talk host who was on both WQAM and 790 The Ticket. Due to Audacy gutting a lot of shows and talent, he’s gone the digital route by launching the Big O Radio Show. The show has made quite the impact already with nearly two million downloads a month. Orlando’s success is proof that it’s smart for terrestrial hosts to consider the digital space even before being forced to do so. There are no guarantees in radio. If your car could break down at any moment (terrestrial radio), it makes sense to save some cash just in case (digital space).

Stream Big O Show | Listen to podcast episodes online for free on SoundCloud

The Big O Radio Show airs Monday through Friday from 10am-1pm ET. The show is on YouTube and also offered as a podcast on most platforms. Interviews and rants are sliced into different segments so people can pick and choose what they want to listen to.

Orlando’s story is inspirational. He didn’t just take his ball and go home when he was phased out of terrestrial radio, he launched a behemoth. We discuss how this is the most fulfilling time in Orlando’s career, the biggest hurdle he faces, and big plans of going on the road. Enjoy!

Brian Noe: What led to you launching the Big O Radio Show in the digital space?

Orlando Alzugaray: Well basically I ended up losing my job. It was kind of funny because I knew I was losing my job. I knew there were changes coming and they were going to start cutting back. If you’ve noticed, a lot of companies have cut back on their talent and they’ve gone more national. There’s a void now in South Florida where there’s very little local programming left and there isn’t a focus on the local programming.

Then the politics are also involved because since there’s only one station now, well that one station also is tied to the teams. Then they’ve also got to play the politics. There is no real objective coverage.

I figured all right, the world’s going digital. You go home every day, it’s Amazon, it’s YouTube, it’s Spotify, it’s Stitcher. Whether it’s your music, your talk, your TV, everything is on demand. That’s where the world is at. I figured okay, there’s a need for the South Florida sports fan that not only lives in South Florida, but is all over the world to find out about what’s going on with the Canes, what’s going on with the Heat and the Dolphins, and the Marlins, and the Panthers, and Inter Miami and all of that. So that’s what I did. I put together a daily show that highlights all of those things. 

We have a one-hour show every week with Ira Winderman who’s been with the Miami Heat since day one. He’s on our show twice a week also doing Heat and NBA reports. We’ve got Omar Kelly, Cameron Wolfe, Alain Poupart and Joe Schad who all cover the Dolphins. I’ve been covering the Dolphins and all the teams in town for 31 years. We give the local listener something that they can really grab ahold of every day that is theirs no matter where they are. They could be in Albuquerque, they could be in Portugal, they could be in Canada, or they could be right here in South Florida.

BN: What are your numbers like in terms of downloads?

OA: The downloads have gone through the roof. We’re up to over 1.8 million a month. We are pacing for 20 million a year and that’s why I told you the South Florida sports fans are all over the world. They’re catching us on YouTube, they’re finding out about the show, then they’re downloading the show, and they’re doing it from all over the world.

The beauty of technology now, it’s made the world so small that if you happen to be in an air base somewhere else in the world and you’re from South Florida, you can tune in to the show live, or you can listen to the podcast, or watch the recording on YouTube. We’re pacing at an incredible rate. We’re doing numbers that are more national than they are local. There’s nothing local here in South Florida that even comes close to these kinds of numbers right now.

The response is there because people can get it on demand whenever they want. They’re getting a lot of content. They’re getting very little commercials and they aren’t getting repetitive content. The listener doesn’t get robbed like they do on local or corporate radio, where they’re telling them to repeat the same things over and over again, sometimes to repeat the same interview from the beginning of the show to the back end of the show because it’s lazy radio. Plus, the listener has to sit there through 25 minutes of commercials. On our show, they don’t have to do that. On our show they’re going to get three hours of different content every single day and that’s why I think they’re chewing it up like Pac-Man right now.

BN: Were you ever surprised and say man, look at these numbers?

OA: I freak out every day. Every day I’m amazed. Today 75,000 and I’m like are you effing kidding me. This is a blessing is what it is. When you’re averaging a million downloads every three weeks, it’s crazy, dude. I never imagined that it would get to this point. Personally, I thought maybe hey man, if we can get to 15, 20,000, you do that over a whole year, that’s a lot of downloads. That’s a great day for anybody. And you start seeing 75, 80, 90; three weeks ago we had 450 from Monday to Friday, we averaged 90,000 a day. I was like I can’t believe it.

I think it’s because there’s a hunger for it. There’s actually a need for it. People want to hear it. We’re doing two million downloads a month practically. In a world of let’s copy Le Batard because there’s a lot of hey, I want to be the next Le Batard and go clowning around and screwing off, we’re back to kind of hardcore sports and it’s exploded. People do want it. There’s a place for everything. It’s growing, man. There’s more room to grow.

BN: What did you do early on to get the word out that you were starting this project?

OA: The beauty is, you put all of our insiders together and myself — I have 96,000 followers — together we’ve got somewhere in the neighborhood of 700,000 followers. When you’ve got that kind of power on social media, all of a sudden everybody’s retweeting the show and where to go. I’m going to date myself, but it’s like that old shampoo commercial, and we told two friends, and they told two friends, and so on. 

That’s also been the beauty of all of this; it’s kind of been all homegrown. We’re trying to do something that we actually connect with the public. We answer their questions. We take their questions. There’s a connection. We read their social media posts. Instead of the corporate world that’s kind of disconnecting from the listener, we’re actually conducting ourselves with the listener. I think they’re noticing that.

BN: Is this the most fulfilling time for you in your broadcasting career?

BIG O RADIO SHOW - YouTube


OA: Yeah, actually it has been to be honest with you because I’m not tied to any corporate entity. I don’t answer to anybody and the only people I can listen to are the fans. They’re the ones that guide us and sometimes they tell us hey, we want to hear more of this or that, and it drives the downloads. I don’t have to have an agenda. The only agenda I have now is to actually feed the people that are like me.

Something you may not know about me, I’m a freak. I’m a born and raised Floridian. I was born in Belle Glade, Florida, which is in the northwest corner of Palm Beach County, raised in Little Havana in Hialeah. I am born and raised for 55 years in South Florida. I love South Florida sports. Anybody that’s known me for 31 years doing radio locally, you know what I’m all about.

Here’s the other thing, radio shows no longer go on the road. We go on the road. We’re going to go to the Senior Bowl. We’re going to go to the combine. We’re going to go to NBA Summer League in Las Vegas. We’re going to go to the draft there in Vegas. We’re going to do all of those things. We’re going to cover the big MMA events and UFC, the boxing events. We’re going to go travel to places that radio stations don’t ever go to anymore. Why? Because we’re not tied down to a big old antenna.

We don’t need a building. We don’t need vans. We don’t need any of that. We don’t have a lot of overhead. What we do want is the content.

We can take off, just me and the producers, and go cover all of the events. We can actually give people what they want and connect with them at the same time and provide for them something that they’re never going to get ever again on local radio because it’s become corporate and it’s not willing to invest individually in each market.

BN: You’ve done a great job of adapting to the current climate. Does it sadden you at the same time to see some stations scaling back and going the cheap route?

OA: Yeah, and you know what they did, right? They did it on FM. For years now they’ve been cutting down on the live DJs. They’ve got DJs that record for 30, 50, 70 stations. Then they just use those cut-ins all throughout the country. They said all right, let’s go cookie cutter. FOX kind of started that because they wanted to highlight all of their national talent, so they bought all the individual stations in different markets so they can create their network. This is the same thing that Audacy is doing now. They’re trying to think national. That’s what they’re catering to. Instead of connecting with each of the individual markets, they’re creating one platform on a national basis.

The sad part is now that there’s less investment in the broadcast business. When I grew up, I grew up with Hank Goldberg, Neil Rogers, Joe Rose. These are the guys that I learned from. These are the guys that I filled in for. I filled in for Hank Goldberg, Ed Kaplan, Neil Rogers. I filled in for all of these type of guys and I learned from them about the business. The sad part is we’re not reinvesting in all of the different markets to create more radio talent.

Radio and newspapers are two of the mediums that have suffered the most, unfortunately. They’ve fallen by the wayside. It’s just sad because there are a lot of young kids that aren’t going to get the opportunity that I got 30 years ago when I was a young guy and they told me hey yeah, we can hire you. We’ll give you an opportunity to be a reporter, a beat guy, those kind of things. Obviously, my career took off from there and I love everything that I’ve done. But yeah, it is sad that there is no longer any more reinvestment in our local communities.

BN: What was the biggest hurdle in your way to get this project to where it is right now?

OA: I think the biggest hurdle is the motivation every day when you have to explain it to people. Some people don’t understand it. Here’s the trick; in my 30-year career, one of the things I also did was I understood the business side of radio. I didn’t just go in to play radio and go cover a team and go break a story. I did all of those things, but I made sure I knew my sponsors. I understood what deals were being cut, what the salespeople were doing, what the station was getting out of it, all of those things. I understood all of that. You’ve got to understand the business side of it too. That’s the important part of all of this. You’ve got to bring both together.

I’ll bring it back full-circle, guys like Joe Rose, Neil Rogers, Hank Goldberg, the people that I learned from, they not only did radio, they did the business of radio. I think that that’s the problem. Everybody wants to play radio. A lot of us can play radio, a lot of us have an opinion, but do you understand the business? The business is what runs you over.

On the digital side, you’ve got to understand the business and then you’ve got to explain it to people. It’s not just a regular commercial, it’s an image. We put borders for our sponsors and we explain that those borders are running for five minutes straight. Then they’re on YouTube for a lifetime because it doesn’t go anywhere. As people are watching it, it’s a perpetual commercial. Those kinds of things. Podcasts have audio commercials inside of it so you’re doing media in a different way. That’s the way it is in digital. You’ve got to go explaining it to the sponsor how your message is getting out because it’s completely different than what they’re used to paying for and used to seeing.

BN: What’s the process been like for you to handle the sales side of your product?

OA: It’s tedious. As I’m getting all of this off the ground, it’s tedious, but it’s important. The same way I told you that it’s important that we connect with our listeners, in the same way it’s important we connect with our sponsors. I’ve been doing this for a long time and I’ve been in studios where there’s a host sitting there and in comes the sales guy that says hey, I sold this account for you. It’s this, this and this. Here’s the script.

The host never met the sponsor, never checked out the product, really doesn’t know the product if it’s any good or not, but is willing to put their name on it. Then just reads the same script word by word every single day. I don’t do that.

I get to know the sponsor. If I like the product, then I do the product. If I don’t like the product, I don’t do the product. I don’t do commercial spots. I do bullet points and I tell you a story. I tell you why I use the product and I do it differently every single day. That’s the difference between someone that actually gives a crap, or the corporate world that doesn’t care and does everything in a cookie-cutter sense. That’s what we’re eliminating. That’s what I’ve never done on my show.

By the way, that did not help me in my business. I’ve had that. The salesperson comes in and says hey, I sold you this. I go you sold me what? Did I go on the sales call? Did I meet the person? Did I test the product out? No, well then I’m not representing it. Then I have to deal with the general sales manager because all they care about is the commission. That’s the difference, man. I’m kind of tired of all of that and I’m so glad I’m away from that.

I’d rather just be myself where I can connect with human beings. That’s kind of been my success for 30 years whether I’m talking to a scout, a general manager, a fan or a sponsor, that’s always been me. While I’m modern enough to adjust to the digital world and social media and crypto and everything else, I’m still old school that I’d rather connect with people face-to-face.

BN: What is it about your show that gives you the biggest rush?

OA: Think about this, man, two years ago on the first day I got 500 downloads. It was 117,000 on Tuesday. Two years later, with the six months in between that I did not do one podcast show — we didn’t do anything from January 1 of 2021 until June 13 — from June 14 until today, we have eight million downloads. That’s what gets me going.

Then when I tell them on YouTube, tell me where you’re checking us out from, and they’re in New Zealand, and in Portugal, and in Canada, and Mexico, and California, and New York, and Atlanta. They’re all over the world. It is amazing when they’re checking in from Malaysia and everywhere else. It is the coolest thing that we can make the world this small on the internet and YouTube and all of that. The coolest thing is how many people we’ve reached already.

BN: What do you want the future to be for the show?

OA: I’d like to grow it as much as possible where we can provide all the coverage for South Florida sports. If the Marlins start spending, then not only do we cover the Marlins, but we’ll go to the owners’ meetings. I want to be the full service local sports talk show for South Florida. We’ve already got the best insiders in town. People already know to come and listen to all these guys and myself for the last 30 years. Now we just want to finish everything off since we started this monster and add all the elements.

Whether it’s the NBA draft, the NBA Summer League, or covering the Heat in the playoffs; if they get to the Finals, we want to be the show that’s going back and forth from the Finals cities, home and away, and giving the local fans the coverage they don’t get anymore from anybody else. What I grew up with, I want the same thing except maybe taking it to just a little bit higher level than what we’ve had in the past. That’s what I want to get back.

Orlando Alzugaray and Omar Kelly... - Miami Dolphins Zone

Look, I don’t have the power or the money. I have the wherewithal, I can figure it out. I can put a whole station together, but I don’t have the money to do that. I would love to put an entire station together and give South Florida fans the real coverage 24/7, but I can’t do that. So for now, let’s create the show that can really kick ass and cover all of the top stories going on in South Florida sports and give the South Florida fan the coverage they want.

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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BSM Writers

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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