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Rider’s 4 Pillars Of A Great Interview

“The goal of every interview should be to leave the audience wanting more and the guest wanting to come back.”

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Before becoming one of the most recognizable voices in commercials, trailers, and radio imaging, Mark Rider spent more than 20 years as a morning show host. During that time, he interviewed celebrities and newsmakers from all walks of life.

In this guest piece for Barrett Sports Media, Rider shares his “4 Pillars of a Great Interview.” They are focused on getting the most entertaining content out of guest interaction. Enjoy!

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Interviewing sports celebrities is something that the majority of program directors have never done. I would even argue that for most just the thought of having to do an interview on-air, live is stomach twistingly terrifying. So without any real hands on experience how are you, Mr. Program Director, supposed to coach and develop your talent into being great at it? Now I don’t mean to discount all the people you have interviewed over the years but that was for hiring purposes not for entertainment purposes.  It’s different and it takes a certain level of courage and commitment that alludes most talent. The good news is that interviewing skills and habits can absolutely be honed and continue to improve as long as the talent are challenged to do so in a positive and nurturing environment that rewards their effort.  

As a former 20 year major market morning host who loved everything about interviewing let me share a few ways of crafting the perfect interview that will help your talent extract original content from their guests that nobody else in town will get.  

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First let’s dissect the mentality of the interview.  Most of the time talent looks at an interview as something finite with a beginning and an end.  I would encourage them to look at it from a more perpetual perspective. If done thoughtfully the best interview can actually go on for months or even years as the talent creates a lasting relationship and rapport with their guest. The goal of every interview should be to leave the audience wanting more and the guest wanting to come back.  

So how does your talent achieve this?  By setting themselves up for the win first and stacking the deck in their favor before anyone even sits down to play the hand. That is done by properly using what I call the “4 pillars of a great interview.” They are prepping, scripting, listening and deviating.

Notice that “winging” it or just “shooting the shit,” is not part of “the 4 pillars of great interviewing.” Larry King, Oprah and David Letterman would never wing it. Your talent must understand that neither can they. If they don’t accept that part of the job description is prepping then they are never going to be great at interviewing and ratings will suffer. And although a producer can definitely help with this process, I firmly believe that the host really needs to do the majority of the heavy lifting on their own to truly be the best.

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Prepping is tedious and not all that fun but without question is the backbone of the interview and today it is easier than ever.  Many of the guests have IMDB pages, Wiki pages, fan pages, as well as their own websites and of course all their social media feeds.  These places are where you go to begin to get to know your guest. Sure there might be some stuff going on in the news about their organization that you should school yourself on, but mostly you need to learn who they are. 

What makes them tick? What interests do you have in common that you can use to connect with them? Some of the best questions I ever came up with were based on things the guest had tweeted about in the last few days.  Why? Because on a radio show they aren’t limited to 280 characters and if they tweeted about somebody keying their car you damn sure know they are going to want to blow off some steam talking about it on your show. Or let’s say they tweeted a picture of them and one of their teammates playing golf last weekend.  Just that picture alone can generate a ton of talk finding out how many balls they lost and whose the better golfer?

Prepping is only part of pre-interview work that must be done.  Next they need to take all the intel gathered and put it into an organized list of well thought out questions.  I like to put my questions into different categories like “Getting to know them,” “getting down to business,” or “getting something out of them.”  

Of course depending on how long you have for the segment will determine how many questions you will need in each category but I would safely say that for a 10 minute segment it would be good to have 3 or 4 questions per category.  And it’s very important that all the questions be open ended so that the guest feels at ease to talk. Here is an example of a closed ended question. “I saw that tweet of your new ride. Is that a Porsche 911?” The only way a guest can answer that question is by saying “Yes it is,” and then some awkward silence not really knowing what you’re getting at.  Now here is an example of the same question asked with an open ending. “Congrats on the new ride. I saw that pic on Instagram. Why don’t you tell us about your new baby?”

See how that just opens the flood gate of possible dialogue?

When a host properly preps and scripts there is a certain sense of command that will make the rest of the ride easy and at this point all they need to do is sit back and listen. 

Listening to what and how the guest is answering questions is equally as important as all of the prep you have done to this point. Are they excited and amped to be on, or are they more quiet and reserved? Have them rely on their producer to find out so they can match the tone at the beginning of the interview, so that it starts off with a vibe that connects the host and guest together as opposed to putting the guest on his back foot.

Great listening skills are what breed most of the magical moments of an amazing interview. Here’s the secret: the magic usually comes from the follow up questions. 

Let’s say the guest is talking about that sweet new ride of his and mentions that it is without question the fastest car he’s ever driven.  Well the host could use this opportunity to see how much he wants to play and lean into that microphone with a soft whisper and follow up with “between you and me, how fast you taken it to so far?”  

It’s in moments like this that your host is getting something out of that guest that nobody else in town has. That makes people tune in longer, come back for more and improve your hosts audience appeal.

The last of the Four Pillars of Interviewing is deviating which means to not be afraid to go off script and go where the guest wants to take you.  Let’s say your guest says “Believe it or not I haven’t gone over 75 yet because the dealer told me I can’t till I get to 500 miles.” After having a good laugh about that and deviating from the script my next question would be “Fastest you’ve ever been in a car and who was it that was driving?” And you’ll be able to tell right away if the guest wants to play and have fun with that topic based on their reaction. The best part is that if they don’t, you can just fall back to the questions you’ve prepped. Never take a guest too far down a road they don’t want to go which is why listening is such an important skill to have and to be laser focused on during the interview. Never get lazy during the interview.

Two more things. Interviewers should be encouraged to not hide behind the mic.  Some of the most memorable interviews I’ve done over the years didn’t take place in a studio or over a phone patch.  

The day after a big game for the Kansas City Chiefs when I was doing mornings at 101 The Fox, I would actually meet up with the limo that was going to pick up a marquee player, go pick them up at their house and while riding with them to their weekly tv appearance interview them on a little handheld recorder.  The conversations were as real as they get coming just after a game and them just leaving the sanctuary of their own home. Instead of being defensive and nervous these guys were calm and fun and genuine because you made it so easy for them to be.  

In Minneapolis I would do the majority of my interviews with Twins players either in the dug out or on field before or after a game where we could just talk shop and they didnt have to do anything but hang out.  They didn’t have to clean up and go to a studio or make a special trip down to their media directors office. I went out of my way to make it easy for them to want to contribute to my show because at the end of the day that is what they are doing.  You really aren’t doing them the favor that they are doing for you.  

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Lastly, the best time of year to establish relationships is in the off season when the pressure isn’t on the players as much.  Encourage and be willing to facilitate trips for your talent to visit training camp or spring training as it’s the best opportunity to get some real face time with veterans and create new friendships with rookies who might turn into marquee players.  I will always remember meeting a shy Maurice Jones Drew at Jacksonville Jaguar’s OTA’s. The kid ended up being a 3 time pro bowler! Because of the time I invested in getting to know him in his early days when my intern made a rude comment suggesting that catching an NFL punt was “easy,” I asked Drew if he’d go up against the intern in a punt catching contest and he said yes!

Talk about memorable on-air moments.  It directly came because of the investment I made in relying on my “4 pillars of great Interviewing.”

Rider is promo and commercial voice working daily with NBC sports NHL and Supercross, CBS sports Monday QB and 4 Sides of the story, Fox Sports North/Wisconsin, the PBR tour, Tampa Bay Lightning& Texas Rangers as well as voicing ESPN 630 Washington D.C, the Shark Miami and many others. Listen to his work at www.ridervo.com and to book him for your next project contact Nate Zeitz at NZeitz@cesdtalent.com.

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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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