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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?”

Brady Farkas

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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.

BSM Writers

Being Wrong On-Air Isn’t A Bad Thing

…if you feel yourself getting uncomfortable over the fact that you were wrong, stop to realize that’s your pride talking. Your ego. And if people call you out for being wrong, it’s actually a good sign.

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WRONG BAD

In the press conference after the Warriors won their fourth NBA title in eight years, Steph Curry referenced a very specific gesture from a very specific episode of Get Up that aired in August 2021.

“Clearly remember some experts and talking heads putting up the big zero,” Curry said, then holding up a hollowed fist to one eye, looking through it as if it were a telescope.

“How many championships we would have going forward because of everything we went through.”

Yep, Kendrick Perkins and Domonique Foxworth each predicted the Warriors wouldn’t win a single title over the course of the four-year extension Curry had just signed. The Warriors won the NBA title and guess what? Curry gets to gloat.

The funny part to me was the people who felt Perkins or Foxworth should be mad or embarrassed. Why? Because they were wrong?

That’s part of the game. If you’re a host or analyst who is never wrong in a prediction, it’s more likely that you’re excruciatingly boring than exceedingly smart. Being wrong is not necessarily fun, but it’s not a bad thing in this business.

You shouldn’t try to be wrong, but you shouldn’t be afraid of it, either. And if you are wrong, own it. Hold your L as I’ve heard the kids say. Don’t try to minimize it or explain it or try to point out how many other people are wrong, too. Do what Kendrick Perkins did on Get Up the day after the Warriors won the title.

“When they go on to win it, guess what?” He said, sitting next to Mike Greenberg. “You have to eat that.”

Do not do what Perkins did later that morning on First Take.

Perkins: “I come on here and it’s cool, right? Y’all can pull up Perk receipts and things to that nature. And then you give other people a pass like J-Will.”

Jason Williams: “I don’t get passes on this show.”

Perkins: “You had to, you had a receipt, too, because me and you both picked the Memphis Grizzlies to beat the Golden State Warriors, but I’m OK with that. I’m OK with that. Go ahead Stephen A. I know you’re about to have fun and do your thing. Go ahead.”

Stephen A. Smith: “First of all, I’m going to get serious for a second with the both of you, especially you, Perk, and I want to tell you something right now. Let me throw myself on Front Street, we can sit up there and make fun of me. You know how many damn Finals predictions I got wrong? I don’t give a damn. I mean, I got a whole bunch of them wrong. Ain’t no reason to come on the air and defend yourself. Perk, listen man. You were wrong. And we making fun, and Steph Curry making fun of you. You laugh at that my brother. He got you today. That’s all. He got you today.”

It’s absolutely great advice, and if you feel yourself getting uncomfortable over the fact that you were wrong, stop to realize that’s your pride talking. Your ego. And if people call you out for being wrong, it’s actually a good sign. It means they’re not just listening, but holding on to what you say. You matter. Don’t ruin that by getting defensive and testy.

WORTH EVERY PENNY

I did a double-take when I saw Chris Russo’s list of the greatest QB-TE combinations ever on Wednesday and this was before I ever got to Tom Brady-to-Rob Gronkowski listed at No. 5. It was actually No. 4 that stopped me cold: Starr-Kramer.

My first thought: Jerry Kramer didn’t play tight end.

My second thought: I must be unaware of this really good tight end from the Lombardi-era Packers.

After further review, I don’t think that’s necessarily true, either. Ron Kramer did play for the Lombardi-era Packers, and he was a good player. He caught 14 scoring passes in a three-year stretch where he really mattered, but he failed to catch a single touchdown pass in six of the 10 NFL seasons he played. He was named first-team All-Pro once and finished his career with 229 receptions.

Now this is not the only reason that this is an absolutely terrible list. It is the most egregious, however. Bart Starr and Kramer are not among the 25 top QB-TE combinations in NFL history let alone the top five. And if you’re to believe Russo’s list, eighty percent of the top tandems played in the NFL in the 30-year window from 1958 to 1987 with only one tandem from the past 30 years meriting inclusion when this is the era in which tight end production has steadily climbed.

Then I found out that Russo is making $10,000 per appearance on “First Take.”

My first thought: You don’t have to pay that much to get a 60-something white guy to grossly exaggerate how great stuff used to be.

My second thought: That might be the best $10,000 ESPN has ever spent.

Once a week, Russo comes on and draws a reaction out of a younger demographic by playing a good-natured version of Dana Carvey’s Grumpy Old Man. Russo groans to JJ Redick about the lack of fundamental basketball skills in today’s game or he proclaims the majesty of a tight end-quarterback pairing that was among the top five in its decade, but doesn’t sniff the top five of all-time.

And guess what? It works. Redick rolls his eyes, asks Russo which game he’s watching, and on Wednesday he got me to spend a good 25 minutes looking up statistics for some Packers tight end I’d never heard of. Not satisfied with that, I then moved on to determine Russo’s biggest omission from the list, which I’ve concluded is Philip Rivers and Antonio Gates, who connected for 89 touchdowns over 15 seasons, which is only 73 more touchdowns than Kramer scored in his career. John Elway and Shannon Sharpe should be on there, too.

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BSM Writers

Money Isn’t The Key Reason Why Sellers Sell Sports Radio

I started selling sports radio because I enjoyed working with clients who loved sports, our station, and wanted to reach fans with our commercials and promotions.

Jeff Caves

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Radio Sales

A radio salesperson’s value being purely tied to money is overrated to me. Our managers all believe that our main motivation for selling radio is to make more money. They see no problem in asking us to sell more in various ways because it increases our paycheck. We are offered more money to sell digital, NTR, to sell another station in the cluster, weekend remotes, new direct business, or via the phone in 8 hours. 

But is that why you sell sports radio?

In 2022, the Top 10 highest paying sales jobs are all in technology. Not a media company among them. You could argue that if it were all about making money, we should quit and work in tech. Famous bank robber Willie Sutton was asked why he robbed twenty banks over twenty years. He reportedly said,” that’s where the money is”. Sutton is the classic example of a person who wanted what money could provide and was willing to do whatever it took to get it, BUT he also admitted he liked robbing banks and felt alive. So, Sutton didn’t do it just for the money.

A salesperson’s relationship with money and prestige is also at the center of the play Death of a Salesman. Willy Loman is an aging and failing salesman who decides he is worth more dead than alive and kills himself in an auto accident giving his family the death benefit from his life insurance policy. Loman wasn’t working for the money. He wanted the prestige of what money could buy for himself and his family. 

Recently, I met a woman who spent twelve years selling radio from 1999-2011. I asked her why she left her senior sales job. She said she didn’t like the changes in the industry. Consolidation was at its peak, and most salespeople were asked to do more with less help. She described her radio sales job as one with “golden handcuffs”. The station paid her too much money to quit even though she hated the job. She finally quit. The job wasn’t worth the money to her.

I started selling sports radio because I enjoyed working with clients who loved sports, our station, and wanted to reach fans with our commercials and promotions. I never wanted to sell anything else and specifically enjoyed selling programming centered around reaching fans of Boise State University football. That’s it. Very similar to what Mark Glynn and his KJR staff experience when selling Kraken hockey and Huskies football.  

I never thought selling sports radio was the best way to make money. I just enjoyed the way I could make money. I focused on the process and what I enjoyed about the position—the freedom to come and go and set my schedule for the most part. I concentrated on annual contracts and clients who wanted to run radio commercials over the air to get more traffic and build their brand.

Most of my clients were local direct and listened to the station. Some other sales initiatives had steep learning curves, were one-day events or contracted out shaky support staff. In other words, the money didn’t motivate me enough. How I spent my time was more important. 

So, if you are in management, maybe consider why your sales staff is working at the station. Because to me, they’d be robbing banks if it were all about making lots of money.  

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BSM Writers

Media Noise: BSM Podcast Network Round Table

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Demetri Ravanos welcomes the two newest members of the BSM Podcast Network to the show. Brady Farkas and Stephen Strom join for a roundtable discussion that includes the new media, Sage Steele and Roger Goodell telling Congress that Dave Portnoy isn’t banned from NFL events.

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