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The Shame of Skip Bayless…and His FOX Bosses

“The FS1 personality made reprehensible comments about Dak Prescott’s depression battle, but don’t forget the executives who pay him and industry double-talkers who gave Charles Barkley a pass after similar remarks.”

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Excoriate Skip Bayless. Eviscerate him, emasculate him. Attach him to a tackling dummy and let Dak Prescott take whacks at him, with follow-up body blows from Troy Aikman. Let his brother, the chef Rick Bayless, cover his body in hot chiles and threaten to deep-fry him until he apologizes.

But please know that the problems with this shameful story — Bayless mocking Prescott, the Dallas Cowboys quarterback, for acknowledging his struggles with depression and anxiety — don’t stop at the microphone of the “Undisputed’’ opinion-spewer. Also to be indicted here, strongly, are the executives who employ this cantankerous cuss at Fox Sports 1, and the shallow-minded sports media peers who selectively admonish Bayless while not caring, say, when Charles Barkley makes similarly insensitive remarks about Paul George’s mental health challenges.

To me, last week’s Bayless eruption is what’s wrong with the profession in a single sound bite. He is paid handsomely not for his expertise but for his penchant to draw cheap attention by making outrageous, preposterous comments. FS1 thinks the formula is successful, even when lowly ratings suggest he has been a massive failure for his reported $5 million a year. So the boss who signed off on his 2016 hiring, Fox Sports CEO and executive producer Eric Shanks, continues to trot out Bayless like a baseball manager who won’t give up on a troublesome, washed-up pitcher. Shanks has been innovative in his career — he helped create NFL RedZone and the yellow first-down line on football telecasts — but the Bayless experiment is much like his glowing puck on long-ago hockey productions.

A grotesquely bad idea.

Media executives tend not to acknowledge their mistakes, you see. In this case, one of the Murdochs might notice the Bayless money drain and shank Shanks. Poaching Bayless from ESPN was the brainchild of Jamie Horowitz, who created the “First Take’’ success story in Bristol by pairing Bayless with Stephen A. Smith. But the hopes of then-fledgling FS1, which thought Bayless’ rants would make big noise, devolved into an undisputed ratings dud. The danger now is that he might be so desperate for attention and metrics that he’ll say anything. Should FS1 yank him from the chair before he sinks to even lower lows on the screech meter?

Let’s just make sure we point out, for the sake of accountability and fairness, that he’s not alone in the sin bin. The sports media, especially fanboy types who play favorites, expose their own flaws by trashing Bayless as a horrible human while giving Barkley his usual passes, which suggests their criticism is grounded in petty jealousy more than genuine disgust and nullifies their professional legitimacy.

Here is what Bayless said about Prescott’s depression issues, which surfaced early in the pandemic and worsened when his brother, Jace, committed suicide: “You are commanding an entire franchise. … And they’re all looking to you to be their CEO, to be in charge of the football team. Because of all that, I don’t have sympathy for him going public with `I got depressed’ and `I suffered depression early in COVID to the point that I couldn’t even go work out.’ Look, he’s the quarterback of America’s team. The sport that he plays is dog-eat-dog. It is no compassion, no quarter given on the football field. If you reveal publicly any little weakness, it can affect your team’s ability to believe in you in the toughest spot.”

The take isn’t hot. It’s heartless, repulsive and a fireable offense. But is it any less disgraceful than Barkley’s response when George, the Los Angeles Clippers star, said he was in a “dark place’’ within the restrictive environment of the NBA Bubble? “I don’t think guys making millions of dollars should be worried just because they’re stuck in a place where they can go fishing and play golf and play basketball and make millions of dollars,” the TNT analyst told Dan Patrick. “That’s not a dark place. The thing that happened in Wisconsin (the Jacob Blake shooting), the things happening with this pandemic, all these people losing their jobs — those people are in a dark place. We are the luckiest people in the world to dribble a stupid basketball and make millions of dollars. We’re never in a dark place. I just think we need to be careful what we complain about.”

Any mental health issue should be discussed with delicate compassion by everyone. If Bayless should be fired for his comment, Barkley should be fired for his. Don’t chastise one because he’s a former newspaper columnist who never played big-time sports and pardon the other because he’s an NBA Hall of Famer. Either focus on the verbal crime itself — and not the popularity or likability of who said it — or return to the grade-school sandbox where too many sports media people belong anyway. This isn’t simply about Bayless, per se. It’s about the shocking inability of network commentators, amid the turbulence of 2020, to understand the most fragile basics about depression.

Yet industry people who openly hate Bayless make it only about Bayless, such as Sports Illustrated media writer Jimmy Traina, who returns here for a second time because he lacks intellectual equilibrium. While obliterating Bayless, Traina ignores Barkley because he likes Barkley. If a critic can’t separate his professional work from personal favoritism, he’s shouldn’t be a critic. Such charlatans only let TNT — and parent company AT&T — off the hook without having to answer for Barkley’s numerous low-blow takes.     NBA star Kevin Love has been a robust spokesperson for mental health. He supported George after his recent comments, tweeting, “… post game speaking about being in a `dark place’ and underestimating the effects of mental health, depression, anxiety — is HUGE coming from a player of his caliber. Was always a fan of PG but now even more so.’’

But Love didn’t address Barkley, either, though naturally mentioning Bayless in a set of tweets: “You want to know why now, and always, it’s important for Dak Prescott to share his struggles … it’s because racial lines play a major part in people’s relationship with mental health — “opening up about a mental illness can feel like giving one more weapon to someone you know can use it against you.”…. Skip missed fact that BECAUSE Dak is the quarterback and leader of America’s team — him outwardly expressing this will lead young men and women of every demographic to be less alone and express themselves openly. Mental health issues rob us of achieving our full potential. … Dak helped move a number of people forward today.’’

Why do people attack Bayless and leave Barkley alone? Are they afraid of Chuck’s wrath? Is it the old Cosellian jockocracy at work? Hell, my phone used to ping every time Barkley torched me on “Inside The NBA’’ — not that my commentaries on “Around The Horn’’ ever exceeded a 7 on a scale of 1 (benign) to 10 (felonious). Think I cared about Chuck? The message of the column ALWAYS is more important than the preservation of relationships, kids. That’s why we’re columnists. We own the independent space.

In that vein, I’m not convinced Fox Sports would have issued a quick statement rebuking Bayless if critics and social media hadn’t railed against him. Shanks is attached to the hip of Cowboys owner Jerry Jones, to the point Erin Andrews actually thanked Jones for conducting an interview last week on behalf of Fox (WTF?). Therefore, Shanks was answering to many when he approved this release: “At Fox Sports, we are proud of Dak Prescott for publicly revealing his struggle with depression and mental health. No matter the cause of the struggle, Fox Sports believes Dak showed tremendous courage which is evident in both his leadership on the Dallas Cowboys and in his character off the field. We do not agree with Skip Bayless’ opinion on Undisputed this morning. We have addressed the significance of this matter with Skip and how his insensitive comments were received by people internally at Fox Sports and our audience.”

Not that Shanks ever would suspend him, which would have been an appropriate punishment. There was Bayless the next morning, back on “Undisputed’’ and not exactly remorseful, claiming he wasn’t aware during his commentary that Prescott’s brother had taken his life. Being aware is a primary part of Bayless’ job description, and if he doesn’t study enough to know the particulars about a prominent NFL player, he shouldn’t be in the chair. Saying his comments were “misconstrued by many,’’ he explained, “The only Dak depression I discussed on the show was from an interview he taped with (talk show host) Graham Bensinger. Dak said that depression hit soon after the pandemic hit, right after the quarantine. I said that if Dak needed help for pandemic depression, he should have sought it then.”

He concluded by describing Prescott as “my quarterback,’’ as if Bayless’ status as a Cowboys fan should supersede any and all misconstruing. I remind you that in a few months, this man-child turns 69 years old.

If Bayless wants to discuss one’s “weakness,’’ I know his. He exposed it years ago when we competed in Chicago — I was the Sun-Times columnist, he was at the Tribune. To his credit, he was passionate about his subject material, more than I could say about the city’s other sports columnists during my 17 years there. But when I’d take a stand, he invariably would take the other side. I happen to be right more than I’m wrong — insert laughtrack here — so it caught up to him. Also, I was writing lengthier pieces and he was confined to a narrow hole down the side of a traditional newspaper broadsheet, which led to internal Tribune disagreements and his resignation. From there, he headed to ESPN and his eventual debate pairing with Smith.

So blame me for Bayless’ transformation as a TV monster.

With networks willing to do anything — unethical, immoral — to spike a ratings book, it’s no coincidence Bayless voiced such a low-brow opinion only a week after Smith’s own regrettable opinion on “First Take’’ about “White privilege’’ — his belief that Steve Nash was hired as Brooklyn Nets head coach only because he’s White. Just as Smith won two days of news-cycle attention — and viewers — Bayless got his two days of eyeballs. Their  programs do compete directly, with Smith and Max Kellerman regularly blowing away Bayless and Shannon Sharpe in the numbers game. And it surprises no one that Smith, who still hasn’t apologized to Nash, seized Bayless’ misfire by delivering a powerful commentary about mental health while sympathizing with Prescott. Of course, he did. Would Stephen A. have done so independent of Bayless’ comments? I doubt it.

Such is the slime game of morning daytime sports talk. Years after FS1 trumpeted Bayless, to the outrage of Fox teammate Aikman, the reckless take-artist appears to have singlehandedly ruined a stalled network and stolen a fortune from the Murdochs. This episode ultimately might push FS1 not to renew Bayless, but TNT still loves Barkley, who recently rebuked Smith and frequently rebukes Bayless, all in the name of televised sports gasbaggery that decency and dignity long ago forgot.

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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