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Meet The Market Managers: Keith Williams, Good Karma Brands Chicago

“I think we just love being creative. It stands out and it does amazing things for our partners.”

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Week 2 of Season 2! Today, the Meet the Market Managers series takes us to Chicago. My conversation with Keith Williams of Good Karma is an interesting one.

Keith is a lifer with GKB, having worked in multiple markets, leading multiple brands for the company. Part of working for Craig Karmazin’s group though is not being married to any ways of doing business. Even lifers aren’t allowed to lean on the idea that “this is how we’ve always done it.”

In our conversation, presented by our outstanding partners at Point-to-Point Marketing, Keith shares why that approach works for him, and why it was part of guiding his search for the station’s new Director of Content. We also talked about competition between Good Karma markets, how Mike Thomas left his mark on the station in a short time, and how to explain the changing media landscape to clients.

Enjoy!

Demetri Ravanos: One of the first things you had to do in Chicago after taking the reigns of ESPN 1000 was hire a PD. That search was largely internal. What were you prioritizing as you were looking for a new leader on the programming side? 

Keith Williams: Just having the vision to pivot quickly to create new opportunities for our team, for our sales and marketing teams, and increase the diversity of our hosts. Those were three things that we really talked about looking to expand. Yes, we had some good internal candidates. We had a few external as well. Danny (Zederman) is obviously who I went with and Ryan Maguire, who you know as he wrote for BSM, we found a spot for in Milwaukee so that he was still with Good Karma.

It was something that obviously my predecessor was very focused on, and he did amazing things with this radio station, moving some of the pieces around, adding Twitch and an app, and of course, the White Sox rights. I thought Danny could really help us get to that next level. He’s added a number of shows already, some specialty things and things specifically on the app. We’re having some fun. 

DR: This is a really big stage. Market number three is a big one to step into for your first programming role. That said, Danny has spent a lot of time with that radio station during his career. You mentioned part of the way ESPN 1000 presented itself while under Mike Thomas’ leadership, so what was it about what Danny that made you say, “I don’t care that he doesn’t have the prior PD experience. He’s the guy!”?

KW: Well, first, he’s really creative. He’s an activator. I knew he was going to move quickly and get things done. He’s got a high capacity to work fast, to work smart, and he’s a really good communicator, and we need that. We need someone that can communicate the vision, the ideas for marketing, for our sales team, and obviously to set the vision for our content team.

We want to be fun. We want to be fast. Obviously, the Bears are always going to be the big team in town, but we also want to continue to bring that personal level of entertainment to our fans.

I think Danny has the ability, and his relationships here with the team, having pretty much worked with almost every single person. This was a great move for him to get the opportunity to prove himself.

DR: So as a new boss coming in, and immediately having to pick a leader of the programming side when you have multiple guys internally interested in the job, how do you go through the process and make sure to build relationships with the people that didn’t get the job? How did you show them that they still have a lot of value to you and the brand? 

KW: That was important. I mean, everybody doesn’t have the exact skill set to manage, to lead and to work quickly and have the ability to communicate across departments. At the same time, everyone that did apply had unbelievable ideas on how to make us better, and we want people’s feedback. We’re not trying to shove things down everyone’s throat. It’s all about listening, communicating, and hearing everybody’s opinions.

We’re a small company. We can pivot on a dime and listen to people’s ideas and feedback and take it, run with it, and make a change. If it doesn’t work, we’ll switch back. So, that’s the beauty of it.

For the people that did apply internally, we took their feedback. We are involving them in the process and hearing their voices. We’re allowing them to help us, because they have a passion for this radio station and market, and deep relationships in the building. Danny and I are both all ears for every single idea that comes across our table.

DR: You mentioned that the company is still relatively small, particularly in terms of media operations. You’ve been with them for a long time across a number of markets in a variety of roles. I always wonder when I talk to people inside Good Karma, what are the standards that are expected across each market? Also, how does the company give the VP/Market Manager an opportunity to establish their own identity and do things their own way?

KW: Craig [Karmazin] gives us a ton of freedom. I do a one-on-one with him each week and I’ve got a list of things I’ll go over, and his usual question back to me is, “was this the right thing to do?” “Does it fit our core values?”.

We look at it like it’s our own business. We are in charge of the revenue. We’re in charge of the expenses and everything left over is cash flow profit that we can then invest in our own people and equipment. So it’s up to us to choose our own path within what Good Karma’s core values and culture are, right?

I think one of the things that I have prided my career on is my communication and follow-through. If I hear somebody wanting something, and maybe we don’t choose to go that direction or we do, we always try to explain the why and follow through. So really, listening to our teammates is key to the growth of how to make this place the best it can be. 

DR: So what sort of information were you trying to gather to make the decision about whether Chicago was the right move for you or not? Was it as simple as “It’s bigger than Madison and I want a new challenge”? Or was there something specific you were looking for before you would say yes? 

KW: I told Craig 20-something years ago when I joined the company, wherever you need me, I am willing to go. So I started off in Madison and had no knowledge of sales, marketing or radio. But I just worked hard and did things the right way, always figuring out a way to hit budget or overdeliver on whatever the key needs were.

Then he gave me an opportunity to run some radio stations in Janesville, which I did for about four or five years. He asked me then to join forces with Sam Pines, who is now running our ESPN LA property. Sam and I worked together in Cleveland for ten years.

I was ready to do something different. So we had the big picture conversation, and I was commuting for a period of time to D.C. and Baltimore, running our ESPN digital sales offices there. We redid the structure of the sales team and then Craig said, would you be willing to go back to Wisconsin? And I said, you know, if that’s where the team needs me, we’ll go. We completely rebuilt the team in my three years there, a year and a half of which, we were probably working from home during the pandemic.

Then when Mike left. It became an opportunity when Craig called and said, “would you be interested in this?”. I said I have to talk to my family first, obviously. My wife was super supportive and asked all the right questions.

This is my passion. I love being in a market. Yes, it’s a bigger market, but the principles are all the same. It’s about the people. It’s about doing the right thing for our partners, and giving our fans the opportunity to consume whatever content we’re putting out there on as many platforms as we possibly can. 

DR: So let’s talk about the people and the partners, because that goes to a question about what happened earlier this month when you guys announced that Carmen and Jurko were moving back to noon to 2 pm. The guys on air mentioned that one of the things they liked is that it meant five days a week they’d get to interact with Waddle and Silvy.

I wonder, as somebody that is looking out for the entire brand, how can something as simple as a casual five or six-minute conversation between two shows, groups of guys that don’t normally have a chance to interact with each other on-air, how does that elevate a brand? Why is an element like that important for getting a station to the next level?

KW: I mean, we see it behind the scenes. Even just yesterday walking around the halls, those guys were talking and hanging out. So, it was a behind-the-scenes conversation, and our whole thing is “let’s bring it to the forefront”.

They have such good chemistry, all four of them. I don’t know if you’ve listened to their crosstalk, Unhinged. Not on the radio. It’s their podcast. Those guys really just absolutely love each other. They respect each other and they can poke and prod just like you do with your friends. I mean, it really is great camaraderie, so why not give it a chance to shine?

You could see some of the feedback on social media. People are really excited to hear that again. So we’re listening to our fans. We’re listening to our teammates. Danny made a great decision.

DR: The other side of that move is it puts Greeny back to 10 to noon. It’s interesting to me that as big of a market as Chicago is, the station is not an O&O for ESPN anymore. It seems from the outside that dropping Greeny for more local programing would make sense, but I know his show had solid ratings in that slot before and GKB has a strong partnership with ESPN Radio which is important. I guess I just wonder why it’s important to keep that connection to the network on air when fans prefer local.

KW: We want the connection. Obviously with ESPN, they are our biggest partner. Plus, you know, Greeny does have a Chicago connection.

Our vision with Danny is to get it as close to all-live as we possibly can, but we love Greeny. We are happy with what he’s doing for us. I know it’s not local, but it sounds local when there’s big news for the market because he has that Chicago background.

DR: I want to go back and combine two things we talked about earlier. You mentioned the idea that this is a small company and I want to tie that to what Mike Thomas accomplished while he was in your seat there.

He pulled off some really cool promotions. He gave away two cars to fans when the White Sox threw a no-hitter. He gave away multiple ad campaigns to local businesses. That sort of creativity and headline-grabbing nature of promotions seems to be standard across all of Good Karma’s properties. Can you take me behind the curtain a little bit here? Is there competition among the local market managers for who can pull off the biggest ideas like that? 

KW: Oh, yeah. 100 percent. We want to one-up each other, for sure. Creativity sells, right? So I think the weirder, the more out there a promotion can be, within the legal guidelines, which are always interesting to figure out, the better.

I think we just love being creative. It stands out and it does amazing things for our partners. I mean, when we did that, Nissan No-Hitter, think of all the earned media exposure that Nissan got from that! And who knew that it was going to happen twice? It was just incredible!

Yes, we definitely have competition for ideas. Our teammates love talking about weird and fun promotions. Our partners love it because they get exposure beyond a radio spot schedule, and our fans like it too because they get to participate and win free stuff, especially when it’s a huge prize like a car. We’re always looking for that type of idea, so we have internal brainstorming meetings on how to do these things all the time.

DR: How do the partners and clients that have been with you for a long time view a promotion like giving away an ad campaign to another business during the pandemic? 

KW: If you think about the partners that we have, some are big businesses, most of them probably are, and some are small. So when we were doing that particular promotion, it was in conjunction with First Midwest Bank, which is now going to be changing to Old National Bank. It was an opportunity for them, right? It was a chance to team up with us to give back to the community. So it was a true partnership. We explain that to our other partners. “Hey, this is something that we’re going to be executing for First Midwest Bank. We’re going to give light to a small business that’s deserving and may not be able to afford a radio schedule in Chicago, Illinois.”

DR: Chicago, in terms of being a radio market, is not Boston, where even if WEEI does good numbers, the trend right now is that The Sports Hub is going to come out on top. ESPN 1000 and The Score have gone back and forth over the years although The Score has had a better run in recent times. When you’re talking to, whether it’s the sales staff or clients, what is it you tell them about the unpredictability and volatility of radio ratings? 

KW: I tell them radio sales and marketing, in my opinion, is all about listening to our partners and their needs, and solving their problems in the most creative and effective way that you can. A ratings point never bought a cheeseburger. Now, I’m definitely quoting one of our teammates on that.

It’s all about the idea and the relationship. Advertising is a real simple formula: audience, frequency and message. If you have all three of those and you’re truly listening to the partner’s objectives, whatever you end up coming up with is going to be the right idea for them, and it’s going to work. That’s why so many of our advertising partners have been with us for so long.

It’s not just in Chicago. That’s everywhere GKB is because we truly listen to what our partners need, and try to get their message out as many times as we can. Radio commercials, promotions, endorsements, appearances, events. Whatever that is, our goal is to sell more hamburgers or cars or windows the next day and the day after that. And you know, if we’re truly listening to people, then we have the ability to grow anyone’s business. 

DR: I think, within the business, it is easy to explain and understand the problems with Nielsen ratings, because we all speak the same language and have the same background knowledge. When you’re talking to a business though, so many of them still put value in that number no matter how often you explain that it doesn’t tell the accurate story anymore because listening shifted or because there isn’t a large enough sample. What is that struggle like? 

KW: It’s all about, are we going to move product, right? At the end of the day, if you have a million listeners and only ten are going to buy a car, that’s the ten that matter.

Our focus is just entirely different. It’s all about how do you help somebody’s business grow with our loyal audience that listens as often as they do for as long as they do. If your message is good enough, it’s going to stand out and it’s going to ring at the cash register. 

DR: Chicago, in radio terms, is becoming more and more unique. You guys are still an AM market. You have a partnership with Hubbard that gives you an HD2 signal, but 1000, The Score, WBBM, WGN, all of the big talk properties, are still on the AM dial and finding success.

Could you see that changing as the generations spending money and leading the charge change? Do you have designs on someday seeing ESPN 1000 become ESPN one-hundred-point-whatever on the FM dial r are you comfortable with the position and habits of Chicago radio? 

KW: We’re very comfortable with our position because I think our mobile app is one tap and you’re already into live programming. We have the ability to promote that and you’re right there. Obviously, with smart devices and smart cars and Twitch, there are plenty of ways to get the content.

If we can just continue to promote not only AM 1000, but the ease of the ESPN Chicago app, you can get content right at your fingertips with seriously, one tap on your phone. I don’t think it matters if you’re on an AM or FM. I would just say the more places you can be, the better. 

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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