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If Black Lives Matter, Dave Portnoy Must Be Cancelled

“In a defining time for racism in America, Barstool Sports — and partners such as NASCAR and Penn National — risk permanent brand damage if they don’t separate immediately from the site’s hatemongering founder, Dave Portnoy.”

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To describe Dave Portnoy as despicable only skims the word choices. He’s a hatemonger and a sicko, no other way to put it, and after taking five showers in stooping to write about him, I am tempted to hire a killer shark to devour his every body part, including a penis if he has one, recalling his career-propelling stunt of posting naked photos of Tom Brady’s then-2-year-old son.

He has used the N-word liberally, approved of blackface costumes and said Colin Kaepernick bears a strong resemblance to Osama bin Laden, referring to the quarterback-turned-activist as “an ISIS guy … Throw a head wrap on this guy, he’s a terrorist.’’ These glimpses of sub-humanity were from 2016 videos that have resurfaced, one in which he belts out Ja Rule’s “Livin’ It Up’’ thusly: “To all my n——-s I’ve been living it up.’’ This is the nutbag who referred to ESPN’s Sam Ponder as “a f—— slut’’ and urged her to “sex it up and be slutty.’’ You wonder what this creep does and says on an hourly basis, an experience from which I’m saved as someone who ignores his digital operation, Barstool Sports.

As always, Portnoy excuses his racism as comedy and satire, a copout Charles Manson could have tapped, I suppose. Like other megalomaniacs, he is too far gone for help. But what disturbs me is how media companies and sports leagues have embraced his brand of fungal disease without regard for the stench they’re inheriting. Peter Chernin, a film producer and former Fox TV executive, enabled Portnoy by buying majority control of Barstool in 2016. ESPN, in another hazy stab during the John Skipper era, tried a late-night show called “Barstool Van Talk’’ that lasted one episode following a Bristol revolt. Inevitably, a gambling company chased the same crude-dude demographic, with Penn National Gaming Inc. spending $163 million in January for a 36 percent stake.

DiBenedetto Finishes 21st at Las Vegas Sunday Night

Then there’s hypocritical NASCAR, which spent millions last year on a Barstool marketing partnership and only bought itself a perception crisis at the worst possible time. The circuit took a historic step in separating from its racist past in the recent drivers’ march that supported black racer Bubba Wallace, yet the relationship with Portnoyism continues, somehow, which is akin to tying a noose in Wallace’s garage. Here was NASCAR’s statement after the death of George Floyd: “While our sport has made progress over the years, there remains much work to be done and we fully embrace our responsibility to help bridge the racial divide that continues to exist in our country. We must do better, and our commitment to promoting equality and inclusion continues and will never waver.’’

Except when keeping a business pact with a racist.

There is no more obvious conclusion, along with water being wet and the sun being warm, than this: Portnoy should be immediately removed from the company he founded before Barstool is tagged permanently as a racist shop. And while I sense he’ll need to be strapped to a gurney and sedated while hauled away by 10 men in white suits, perhaps a company coup finally was set in motion Thursday against the man-child who claims he’s “uncancellable.’’ A Barstool host who calls himself PFT Commenter, from a show called “Pardon My Take,’’ ripped Portnoy for not considering the company’s minority employees when he refused to apologize this week  — “I’m not gonna bend the knee,’’ he said — for his past comments.

“When I saw that clip of ignorant and racist comments from the 2016 Colin Kaepernick rundown, I, like a lot of my colleagues, was mad and embarrassed,’’ wrote the PFT character about the videos, which included shameful behavior from Barstool hosts Dan Katz and Kevin Clancy. “To put it bluntly, it’s especially f——- -up that our black coworkers have been unfairly put in the position of choosing to either a) accept racist remarks, or b) publicly fighting with their boss.’’

This followed a podcast by some of those minority employees — led by former NFL lineman Willie Colon, host of Barstool’s 2Biggs podcast — who lashed out at Portnoy. They titled the podcast N.I.G.G.E.R., short for “Now It’s Gonna Get Extremely Real.’’ Said Colon: “I said to Dave, for the people who work here and work for you, we’re kind of offended by it, so when you throw your middle fingers up at the cancel culture, you’re really throwing your middle fingers up at us. And he was like, `I hear you, but I have a bigger following than you, I write your checks, and the people who support me and Barstool help me write your checks, so f—— eat a dick.’ ‘’

https://twitter.com/2BiggsPod/status/1278460574440009728?s=20

For a nanosecond, I thought they might be duping us in a scam for more Barstool attention. But I don’t think so. Publicly, company executive Erika Nardini refuses to condemn Portnoy, her bread and butter, tweeting this week, “Change doesn’t come from cancellation, and it will never come from everyone having f—— consensus all the time. It comes from difficult times and strong people who see new opportunities and take risks.’’ But privately, if she’s smart, she will feel the tempest in her house and find a bulldozer to remove the toxic waste. When the subject is race, amid this country’s most heated year of racial tension in decades, no one is play-acting. This is all very real and all very dangerous.

“I don’t know exactly how to fix this short of making Willie Dave’s boss,’’ wrote the PFT guy, “but I do know that what’s happened over the last four days is not going to work in the long term.’’

NASCAR isn’t commenting. Nor is Penn National — my two email inquiries went unanswered. So, their silence will be interpreted as a tacit acceptance of All Things Portnoy, which means those companies aren’t as committed to stamping out racism as they claim, such as Penn National’s stated vow to “stand united against hate, racism, violence and intolerance of any sort and salute all the peaceful warriors and protesters on the front lines of social injustice making their voice heard.’’ Where the company erred was allowing Portnoy to have all editorial control over content, thus nullifying supposed “guardrails’’ prohibiting “language that encourages underage gambling, illegal bets, or comments that might be deemed as harassment or discrimination of women or minorities, for example.”

They sold out to a madman, a compromise that should be known by people of all races when they visit Penn National’s 41 gaming and racing properties in 19 states and live betting properties in six states — Barstool Sports book app included. One reason for the sellout: Portnoy has had such a hypnotic hold on his “Stoolies’’ sheep — even as a pandemic day trader — that Penn National stock jumped 15 percent after he dropped the name on CNBC’s “Mad Money’’ last month. Never mind the workforce that Penn National could have salvaged without the Barstool investment; after furloughing 26,000 employees in April, the company filed notice it will lay off 233 people next month at its corporate offices. The executives sure love that stock bump … but for how much longer?

Penn National Gaming on Twitter: "Today we rang the bell. #NASDAQ… "

Who does Portnoy think he is, Warren Buffett?

“I’m better than he is. That’s a fact,’’ he said, even after being banned from E*Trade for a curious June 10 transaction.

I wonder what those aforementioned “peaceful warriors’’ would do to Portnoy if he stepped into a Black Lives Matter protest. By comparison, the killer shark might look tame. When activist/commentator Jemele Hill drew attention to his past videos, he mocked “cancel culture’’ and tried to justify his incendiary words by blaming societal shifts. “I’ve been doing this for two decades. I’ve made fun of every group of people, every race, every creed, every culture — you name it, we’ve made jokes about it,” he said in a video. “So if the No Fun Club, if the cancel culture wants to go back blog by blog, video by video, day by day, week by week, month by month, year by year, decade by decade and comb through everything we’ve ever f—in’ said and done, yeah, you’re gonna find a few jokes that missed the mark, that things if they are said today, you’d be like, `How’d they f—in’ say this? What are they, idiots?’ But times change, sensitivities change, cultures change. When you’ve been doing it as long as we have, things f—in’ change!”

That much is true. Societies do evolve for the better, the wiser and the fairer, leaving behind the cavemen. I just wonder, in a 2020 media context, why anyone interested in sports, regardless of demographic, would listen to this trash and not opt for a cooler, more enlightened host such as Jalen Rose or Colin Cowherd. Or even Pat McAfee, who has Barstool tendencies but was wise to cut the cord for more mainstream media pursuits.

Barstool Sports Founder Takes Over "Call Her Daddy" Instagram Amid ...

Portnoy tends to retaliate via targeted harassment, meaning my social media sites might be bombarded by the same cretin followers who pelt other critics. But maybe not. If Stoolies must decide between Barstool and Portnoy in a coup situation, I think Van Halen wins. David Lee Roth always can be replaced by a tamer Sammy Hagar.

Besides, I am not the story. The story is why companies in position to cancel Portnoy prefer to keep feeding the monster. “Whenever you try to cancel us, and do these movements that pop up once every couple years, it only makes us stronger,” he said. “Normal people only want an escape for a couple f—king seconds from this f—ked-up world, and that’s all we’re trying to do. And it just makes them like us more. … Keep trying to cancel us. We’ll just keep growing stronger. And when you’re miserable and dead and f—king off doing your own thing, in the next decade, we’ll still be here, doing us, and you’ll still be losing sleep about it. That’s just how it goes. You see this mug? Ain’t going anywhere.”

The killer shark is thinking otherwise. So is Willie Colon.

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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BSM Writers

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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