If a bucket list of jobs within the sports media business existed, Jen Lada would be busy crossing off all of the incredible opportunities she’s had. Whether it’s hosting SportsCenter, doing incredible features for College Gameday or hosting a morning radio show, Lada has enjoyed a career that’s taken her to some of the most coveted positions in the business.
But she didn’t get there without some early hardships. However, a lot of hard work combined with exceptional talent has landed her both an incredible TV and incredible radio job. Lada talked about both the television and sports radio space she now enjoys. Plus, a lot more.
Tyler McComas: I know it’s been a bit since you were hired at ESPN Milwaukee, but how has the morning show gone?
Jen Lada: Honestly, I’m having so much fun. It’s like anything else, there’s a learning curve and a transition period, but I feel since football season has wrapped we’ve really hit a stride.
The chemistry, information, and entertainment is there, and I feel most mornings like this is the most fun I’ve had in my career. I’m so thankful to Good Karma Brands for taking a chance on me. I had very little radio experience, but they felt like I could be a provocative voice in the space and they gave me this opportunity. We work really hard to not try and take ourselves too seriously.
That sounds kind of like an oxymoron, but that’s our emphasis every day. It’s a morning show, so we want to have fun and for our listeners to have fun, while also discussing the topics of interest.
TM: You have a background with college football, your co-host Mark Chmura is a former Packer and the Bucks won an NBA Title last year. What’s the No.1 focus when it comes to content?
JL: It’s a good problem to have. Truthfully, Packers are a 12-month topic in Wisconsin. And the NFL has done an exceptional job of making sure they are a round-the-year topic. We do focus a lot on what the Packers are doing and what Aaron Rodgers is doing.
As the Bucks become more relevant and have success, that fan base continues to grow and we have fun talking about that team.
TM: What’s been your impression so far of new program director Ryan Maguire?
JL: (laughing) Poor Ryan has been stuck in training. Since he signed on, we’ve very much looked forward to chatting with him. We joke on the show about how we haven’t had a boss for the last year and that’s the only reason we’re still on the air. It’s very tongue in cheek, but there was some of that, where at times we were like, hey, are we doing a good job? Is this good content? Are people listening?
That’s not to say anyone was negligent, it’s just we didn’t have an immediate supervisor. We’re super excited as a show to have someone like Ryan, who has so much experience and knowledge. It will make us that much better. We joke around and say, man, if you listen to us now, just wait until we get some direction.
TM: How can we be better at putting more women behind the mic in a full-time role?
JL: There have to be executives that are willing to take that risk, and I don’t think it’s that big of a risk. It’s more of a perceived risk, than an actual risk. But I think you also have to have women who are confident enough to step into that space and be willing to fail. Be willing to struggle.
We talked about Tiger Woods this morning on the show and how when you recalibrate your thought process, so that it’s not a zero-sum game, and sports often is, because there’s winning and there’s losing. I’ve referenced Ricky Bobby. “I you ain’t first you’re last.” But with regards to Tiger Woods we talked about how this Masters tournament was a step in his journey back and the bravery it takes to work out those kinks and find out where you stand in a very public space.
My point this morning was this is a checkpoint, not a finish line. And I think women have to be willing to say, this is a checkpoint, not a finish line when you step into spaces where women have not traditionally existed or thrived. Again, it’s not always because they haven’t been given the opportunity, but I think you have to let yourself off the hook a little bit. This idea of being perfect or knowing everything is so stifling, I think it limits a lot of people from taking those chances and putting themselves in positions where they can succeed because they’ve been programmed to believe they can’t.
TM: We tend to focus on putting more women on the air, and rightfully so, but is there anything positive to report when it comes to more women getting opportunities in sports media?
JL: You’re seeing a lot more women getting opportunities to do things they haven’t done in the past. A lot of play-by-play spaces, Lisa Byington with the Bucks, obviously. Mina Kimes on NFL Live on ESPN. But they still take their share of unnecessary or unwarranted criticism, because there’s still a portion of the population that doesn’t want to hear women talking about sports. It is archaic. We make up a huge portion of the fan population. Ostensibly, these women are educated in the things they’re passionate about.
When I started in sports, women were forced to compete with other women for very few, very specific opportunities. We were 1 of 10 in a city or 1 of 20 on a beat. Talk about an NFL press box and it might be one of thirty or more. The ratio was just horrible and I think that programming contributed to women feeling – and sometimes acting territorial about their space.
As women are given more opportunities – both in quantity and variety – you’re seeing a lot more championing, support, and friendship between women in the industry. And that, to me, has been the best development over the last 20 years. As executives continue recognizing the value of diversity of experience and thought, it’s obviously been great to see those ratios change. With that progress comes the welcome realization that celebrating another woman’s talent and successes doesn’t invalidate yours or jeopardize your job security.
TM: You’re in a marriage where both you and your husband have jobs in sports media. What are the challenges and positives of that?
JL: Number one with a bullet, no questions asked will always be the schedule. We work very unorthodox hours and if we’re both working unorthodox, unusual hours, you end up really having to do a lot of maneuvering and navigating and staring at a calendar going to figure out how are we going to make this work.
Fortunately, moving back to Wisconsin means we have a great support system. My family is in the area, my dad and mom are a huge help with our three kids. It’s never felt like we can’t do this.
The advantages? We talk a lot about the things we’re working on. We strategize and brainstorm ways to be better. I’ll have an idea about something or an opinion about something and I’ll throw it out there, and he’ll be my sounding board and play devil’s advocate. That helps me develop my position on things. That’s a huge advantage, to have similar passions and to really understand how the industry works.
You can be very knowledgeable about sports and be a really good broadcaster, but if you don’t understand the ins and outs of the industry, it can be a struggle. Using each other as a sounding board has been a big reason why we’ve been successful.
TM: You’ve been able to have so many incredible roles at ESPN. Is there one that’s stood out as your favorite?
JL: It’s just crazy how my journey has been at ESPN. I was hired 7 years ago to join Colin Cowherd on his radio show. I was the Joy Taylor of the show. He obviously took his talents to Fox and I’ve never begrudged him for that. I think it’s fantastic and I always say, get your money and opportunities when they come around. But it definitely left me in a lurch, where I was like, “Okay, I thought that’s what I was going to do, and now that’s gone. How do we still make something of ourselves at the national level with this ESPN thing?”
Again, being hired as a radio talent, we’re talking about two very different departments at ESPN. They’re run by different people. So I really had to sell myself and knock on doors and sell myself as a television talent to people at ESPN who had no idea who I was, because I was hired by the radio department.
I did a lot of Baseball Tonight when I first started. 2am shows are a grind. (Laughs). I transitioned into some Mike and Mike. I’ve hosted First Take, obviously SportsCenter, which is such a thrill. It’s one of those bucket list items when you get into the business. I remember on my first day at ESPN I took a picture inside the SportsCenter studio.
I think the most fateful interaction was me being picked to be on College Gameday because it’s one of our premier shows and has been for a very long time. It has an exceptional reputation because it has the very best people working on the show. I think Rece Davis is one of the most talented people I’ve ever worked with. The analysts are prepared and informed and they have so much experience in that space.
Obviously, Kirk Herbstreit is one of the premiere stars in our industry. When I got on the show, Tim Rinaldi And Gene Wojciechowski were the feature reporters and I really had no idea how talented and exceptional they were at their craft. I was just kind of being thrown in there and it was like, “okay newbie, swim”.
I just threw myself into college football wholeheartedly and consumed everything that was available to me, whether it was reading books or watching old games, just starting to get a feel for the tradition and pageantry and the passion for college football. Once I threw myself into that I was absolutely hooked. I said this is the greatest thing I could ever do with my career.
TM: How fulfilling is it doing feature stories for College Gameday? I know you’re not doing them to fulfill yourself, but what’s it like when you move an entire audience?
JL: I think the most important thing about existing in the feature space is that recognizing early on that these aren’t your stories to tell. I think the only way these things become something, is because somebody was willing to share their pain. Somebody was willing to be vulnerable to allow cameras and microphones and people, virtual strangers into their homes, and talk about things that have really affected them significantly.
It’s not always negative, it’s not always about death or loss. There are times when we’re talking about the other spectrum of emotion. But it does feel like the ones that resonate with people the most are people being transparent and vulnerable. That’s why Hilinkski’s Hope was such a strong reaction. It’s why the story we did with Ryan Day about his father’s suicide when he was a child, which he had only recently come to grips with himself as an adult. It’s why the story of San Hartman at Wake Forest, quarterback, talented kid, comes from a great family and not a lot of people knew what he went through and the loss of his brother several years prior.
We got a call letting us know that Mike Vrabel showed that piece to his team on a team-building day to convey to them it’s ok to not be ok. And when you’re struggling, we have the resources here available to you to help. I think it’s the ripple effect of those stories that I’m most proud of. Certainly, the impact they have when they’re first seen, but when they’re shared and passed on, or when someone watches one and says, here’s a coach or a player, where you think they’ve got it all figured out and they’re at the top of they’re game and the world at their feet; and they decide to be vulnerable and talk about their challenges, I think it helps normalize some things. I think that’s when sports are at their most powerful, when it brings people together and unifies communities and groups.
Would Local Radio Benefit From Hosting An Annual Upfront?
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.
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.”
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.
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?”
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.”
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.