His wife, Jenny Dell Middlebrooks, a former Red Sox sideline reporter and now the Emmy-nominated lead college football reporter for CBS Sports, is with him at the ballpark. So are their daughters, Madison, 6, and Makenzie, 5.
Middlebrooks’s job has kept him away from their new home in Boynton Beach, Florida, too often lately. Of the Red Sox’ 162 games this season, he will end up being part of around 120, between NESN and WEEI, the club’s flagship television and radio outlets, respectively. (Globe owner John Henry is principal owner of Fenway Sports Group, which owns the Red Sox and 80 percent of NESN.)
“I’m in a span of being home for something like six of 50-something days,” Middlebrooks says. “Our careers require a lot of flexibility and sacrifice, and we both understand that because we’re both in this business, but it’s so hard when we’re not all together.”
The hectic lifestyle of a couple juggling family and career brings an additional layer of chaos, more so recently because of some literal moving pieces. In mid-June, the family moved two streets away from their previous home in Florida, mainly because the new address offers better school options for the girls.
With Middlebrooks in Boston or on the road with the Red Sox, Dell had to handle the logistics on her own.
“This one was tougher than when we moved cross-country [from Scottsdale, Arizona] in 2018,” he says. “Which she also had to do alone.”
“This one did not go smooth,” she confirms.
With their daughters out of school for the summer and the move at last complete, Dell and the girls have zipped up to Boston for a June visit.
For five days, home has come to Middlebrooks.
There is no more fitting locale than Fenway Park for this reunion. Dell, now 39, and Middlebrooks, 37, connected here in 2012 — she the bright-eyed newcomer on NESN, he the Red Sox’ wide-eyed rookie third baseman. It was here that, amid breathless coverage in the gossip pages — and questions about the line between sports media and the teams they cover — their relationship quickly blossomed into real love.
This summertime visit gives their daughters a chance to further forge their own connection with Dad’s workplace, and Mom’s former one, and get to know the place where the early chapters of their family story were written.
At one point, while the family and a reporter walk along the Dell Technologies Suites (no relation to Jenny) on the ballpark’s third level, the girls point out the plaques honoring members of the Red Sox Hall of Fame.
Middlebrooks smiles. “The other day, one of the girls asked me where my plaque was,” he says, deploying the self-deprecation that has served him well as a broadcaster. “ ‘Well, honey, you see, Daddy [only] hit 43 career home runs. . . . ’”
He may never be a Hall of Famer. But Boston and Fenway have given Middlebrooks and Dell something better, as they see it. A home, a place where they can come back to find their bearings, no matter their official address and how many moves she must oversee. A family. And a love story that has lasted.
Arriving at the NESN suite for an interview, Middlebrooks and Dell are dressed in what could be called their Fenway best — she’s wearing a Red Sox jacket, while Middlebrooks is in his NESN gear, and yet both look like escapees from a Polo Ralph Lauren ad. They sit down and immediately start conversing — and this reporter realizes he is in for a transcription nightmare.
While the girls fiddle with their iPads, chirping happily away, the couple banter with a rhythm that even the best sit-com writers struggle to nail. Both build on what the other has said, with frequent bursts of laughter. None of it is conducive to effortless note-taking.
“It’s a good thing that I’m type A …” she is saying.
“… She is type A. She’s the organized one,” he says. “I grew up in baseball, where everything is taken care of for you and we’re totally spoiled. She’s like, everything is going to be scheduled …”
“It has to be,” she says with a nod.
“It has to be with as many moving pieces as we have.” He rattles off an assortment of sports and other activities the girls are involved in.
I joke that they must have a giant, complicated schedule taped to the refrigerator.
Dell whips out her phone and opens up an app featuring color-coded schedules for the family. “I’m pink, he’s green, the girls each have their own color,” she says with more than a hint of pride. “It’s completely organized.”
“So she’s actually Type A-plus,” Middlebrooks deadpans.
The conversation turns to their beginnings in Boston. Dell, a Connecticut native and University of Massachusetts Amherst graduate (she remembers celebrating in her dorm when the Sox won the 2004 World Series), was hired by NESN in 2012 after a brief, mostly behind-the-scenes role at ESPN. She had big shoes to fill: popular sideline reporter Heidi Watney had just left the network and would join the MLB Network a year later.
Dell was green, and NESN delayed her debut during spring training so she could get more practice. When it became clear she wasn’t quite ready for live shots, the station decided to tape her in-game segments ahead of time. Russ Kenn, the producer of NESN’s Red Sox broadcasts at the time, took the unusual route of emailing members of the Boston media that spring, asking for ideas about how to help her become more comfortable.
“When we started with her, she had a lot to learn,” says Mike Narracci, the director of NESN’s Red Sox broadcasts back then. “But she was smart and eager and coachable. You just want to see progress each game, and she just kept getting better and better until she advanced to where she is now.”
Don Orsillo, NESN’s play-by-play voice from 2001 to 2015, says it helped that Dell quickly developed chemistry with him and Jerry Remy, the beloved color commentator who died in 2021. “She clicked with us right away and was a part of what we did instantly,” says Orsillo, now in his 10th season of calling San Diego Padres games. “She had a similar sense of humor to ours… It felt like we had worked together for years.”
Dell was making her name in Boston. She didn’t know it yet, but her future husband would soon arrive in the city.
In May of 2012, after an injury sent Kevin Youkilis — the popular but fading third baseman — to the disabled list, Middlebrooks got the call. He was the obvious choice. At the time, he was ranked as the best prospect in the Red Sox organization (one spot ahead of future All-Star Xander Bogaerts) and 51st overall in all of professional ball by Baseball America.
Dell and Middlebrooks had first met a couple months prior, during spring training in Fort Myers. An assortment of unusual coincidences later made them wonder whether they were destined to meet.
Here’s one: Dell’s childhood best friend was Lexi Allen — now Lexi Solder, having married Nate Solder, a former tackle for the New England Patriots. When Nate was with the Patriots, he lived with backup quarterback Ryan Mallett for a time. Mallett, who died in June 2023, was Middlebrooks’s best friend growing up in Texarkana, Texas.
When Dell started at NESN, she had intended to seek out Middlebrooks. “When I first got the job and was still at ESPN, a friend of mine knew Will. I mentioned that I was nervous about going into the clubhouse for the first time, and she said, ‘I have a friend, Will Middlebrooks, he’s going to be a rookie this year. He’s probably just as nervous as you are.’” So during her first visit to the clubhouse in spring training, Dell made a beeline for his locker.
“I was No. 83, stuck in the corner, down by the food room,” Middlebrooks recalls. “I was 23, and definitely nervous.”
“So I walk in,” Dell says, “And David Ortiz immediately gives me a hard time about my shoes, ‘You! New girl! What’s on your feet?’ So I wasn’t that inconspicuous, I guess.”
She pauses and breaks into a big smile. “Will’s was the first locker I went to. Turned out to be a great decision.”
Asked about the early stages of the relationship, Dell demurs, saying the couple prefers to keep that period private. But after the 2012 season, the two hung out in a group of mutual friends. Around this time, Dell approached her managers at NESN.
“We wanted to go through the proper channels when we even started talking to make sure that this was going to be something that was OK,” Dell says. “And we were basically told, Keep it under the radar, because you don’t know if this is going to be a quick little relationship or turn into something more.”
The couple tried to keep their romance under wraps during the next season, which would prove an emotional one at Fenway Park.
In the aftermath of the Boston Marathon bombings in April of that year, the Red Sox played a role in the city’s healing. Before the first game at Fenway after the bombings, Ortiz addressed the fans and gave the city a rallying cry that would endure. “This is our [expletive] city,” he declared, “and nobody is going to dictate our freedom. Stay strong.”
Middlebrooks, for his part, tweeted the morning after the bombings: “I can’t wait to put on my jersey today … I get to play for the strongest city out there. #BostonStrong.”
“That year, my role really turned from being the Red Sox reporter to — I don’t want to say a voice to help the city, but every game we had someone on [the broadcast] who was deeply affected,” Dell says.
“It became part of our identity that year,” Middlebrooks adds. “We wanted people to be part of us, that we were all in it together.” Meanwhile, on the field, the emboldened Sox — a last-place team the previous season — were marching to the playoffs.
The quest to keep their relationship private was mostly successful, though the rumor mill did not rest all season. The Boston Herald’s “Inside Track” gossip column — which referred to Dell as a “baseball babe beat reporter” and “bodacious brunette” — occasionally hinted at their connection with lines such as this one in November 2013: “NESN vixen Jenny Dell and Red Sox infielder Will Middlebrooks [seen] hanging together at Howl At The Moon.”
Dell emphasizes that when they were at the ballpark, they were fully focused on their jobs, which for her meant tracking the performance of all the players. She jokes that not much digging was necessary to know what was going on with Middlebrooks.
“There were times when he was in Triple A, rehabbing an injury, and I’m up with the big team, and doing reports on how he’s doing in the minor leagues,” she says. “‘Well, he went 3 for 4 today with a homer, I am well aware.’”
“It was interesting,” he says, “because especially at the beginning of a relationship, you’re in the honeymoon stage and you want to be out and about and do fun things, and we had a very different start of our relationship. An unconventional start.”
The couple moved in together that season, knowing they couldn’t be seen out in public, but also that their relationship was deepening. And, as Middlebrooks puts it, “You learn about a person real quick when you’re living together, and at a ballpark together, and traveling on the road together.”
You find out who is Type A-plus, it’s suggested.
“He found who he was really about to get involved with,” she says, laughing.
Their efforts to keep things professional at work made for some awkward moments during the end of that season.
One of those moments took place as the Red Sox celebrated at Fenway after defeating the St. Louis Cardinals in Game 6 of the World Series, clinching their third championship in the span of a decade.
“I’m down on the field doing all the interviews,” Dell recalls, “and I’m bear-hugging Papi [Ortiz] and [Mike Napoli] and all the guys, and then with Will, I shook his hand.”
“She shook my hand,” Middlebrooks repeats, shaking his head.
“And I was like, ‘Congrats, Will!’ Inside I just wanted to grab him and be like, ‘You just won the World Series!’”
Later, after the party moved from the locker room to a club, they weren’t so subtle, at least in Narracci’s recollection.
“We don’t recommend you date a player, obviously, and we communicate that,” Narracci says. “But I didn’t know they were together with my own eyes until the celebration at Game On after the win. I saw them together and was like, ‘Oh, OK, great,’ and winked at her across the room. I was happy for them, because I like both of them and thought they were a great couple.
“You can’t stop who you love and who loves you, you know?”
On New Year’s Eve that year, Middlebrooks and Dell at last confirmed that they were together.
On his Twitter account, Middlebrooks posted a picture of them together with the message, “Happy New Year from us to you! Here’s to a great 2014! @JennyDellNESN.”
It had been an unexpected Cupid who encouraged them to go public.
“That was actually Jerry Remy’s idea,” Dell says. “He was like, ‘Hey, you and Will are at the point now when you’ve been together for at least a year. Go ahead, let people know.’”
Most people seemed thrilled for them, she says. But there were valid and serious ethical questions that had to be dealt with. Female journalists have endured decades of struggle to be treated seriously as reporters. Women have worked hard to shake off the persistent trope of the reporter who becomes involved with her sources. It did not help that there had been blurred lines and salacious rumors with some of Dell’s predecessors at NESN.
A few weeks after Middlebrooks and Dell’s announcement, Abby Chin, the Celtics sideline reporter for NBC Sports Boston, told a New Hampshire radio station: “As a woman in this business, we are constantly climbing an uphill battle when it comes to credibility,” she said. “So even the slightest nick in your armor could have a much larger effect. . . Women in this business don’t get three strikes, they get one.”
(The debate picked up again a few years later, when Jessica Moran, a reporter for Comcast SportsNet New England, resigned after questions surfaced about her relationship with Red Sox manager John Farrell. Former Globe sports columnist Jackie MacMullan put the conundrum this way: “I know when I became a journalist, you had to be objective. That was the rule… It’s impossible to be objective about someone when you’re in a personal relationship.” )
“I understood the weight that it carried as a reporter,” Dell says. “You don’t want to be looked at a certain way. There’s a lot of women in the industry that are looked at in different ways because of relationships.”
In January 2014, NESN management, partially in response to backlash about Dell’s relationship with Middlebrooks, moved her to a studio role.
That February, during spring training, Tom Werner, the chairman of Fenway Sports Group, said she was free to leave the network before her contract was up, if she wanted. “It wasn’t a black-and-white decision, because maybe she could divorce her personal life from her professional one,” Werner said at the time. “But in the end we decided it was time to move on.”
“It wasn’t a fling,” Dell says. “I was willing to risk my career, because I understood how it was going to look when it did come out. I knew there was a reason it was worth it. And here we are, married for 10 years with two kids. I guess it all works out how it’s supposed to.”
“It wasn’t really until we got engaged,” Middlebrooks says, “that people realized, Wait. They really love each other.”
Dell left the network in May, landing at CBS Sports a month later as an NFL sideline reporter. That summer in Newport, Rhode Island, Middlebrooks proposed to Dell. How confident was he that she would say yes? He had a surprise party of friends and family waiting at a nearby restaurant.
While Dell worked her way up the ranks at CBS Sports — she moved to college football after a year and grew into a star in the role, earning a Sports Emmy nomination this year for Best Sideline Reporter — Middlebrooks’s career took an unexpected and painful trajectory. Troubles getting on base and a string of injuries derailed his promising beginnings, when he looked like he’d join Mookie Betts, Xander Bogaerts, and Jackie Bradley Jr. as part of an exciting young core. In December 2014, the Red Sox traded him to the Padres for backup catcher Ryan Hanigan.
“It felt like something bad happened every year,” he recalls. “Broke my wrist at the end of 2012, and then after that it just snowballed. Calf, finger, disc in back, two shoulder surgeries. I’d play a few months, things would be going well, injuries would happen, I’d come back, finish the year great, and I’d get a job the next year.”
The news off the field was much better. On Valentine’s Day 2016, the two tied the knot during a ceremony over a long weekend in Arizona, where they lived at the time. The song for the newlyweds’ first dance was Ingrid Michaelson’s version of “Can’t Help Falling in Love.”
Middlebrooks’s baseball fortunes, however, took a turn for the worse and refused to change course. After abbreviated stints with the Padres and Brewers, catastrophe struck in 2018 while he was in spring training with the Phillies. In a collision with a teammate, Middlebrooks fractured his left fibula and suffered ankle damage.
The injury happened the day after they had found out Dell was pregnant, which had been an arduous journey of its own. “Two and a half years, 524 shots, over 1,000 pills, multiple procedures, and countless tears,” she wrote on social media at the time, “all for this moment.”
“The highest of the highs and the lowest of the lows,” Middlebrooks recalls.
After several months of rehab, Middlebrooks was still struggling to walk. It was then that “I realized I probably wasn’t going to play again,” he recalls. In January 2019, three months after Madison was born, Middlebrooks retired from professional baseball. Just 30 years old, he grappled with the abrupt end to his once-promising career.
“I was miserable,” he says. “It was my identity, who I always was, and that was gone.”
Middlebrooks thought he might go into coaching like his dad, Tom, who coached several sports, including baseball, in Texarkana for more than 40 years. But with a newborn and dreams of growing their family, he didn’t like the idea of riding buses from town to town in the minors in the long quest to get back to the big leagues as a coach.
Besides, Dell had other ideas, along with some excellent contacts.
“I called CBS,” she says.
“She came home from CBS HQ one day in early June, and she was like, ‘Hey, you need to give this [broadcasting] a try,’ ” says Middlebrooks. “ ‘Get a haircut. Find a suit. Maybe read up on these five topics.’ ”
“I hadn’t watched a pitch of baseball, because it broke my heart and I was still in that state. And I was like, ‘Absolutely not.’ She had already told them I was going to do it, and I was kind of pissed.”
“He needed to get off his …,” she says, smiling. “So I forced his hand. As much as he didn’t want to do TV at first, I knew he would be good at it. Sports are always on in our house, and he was so good at forecasting what would happen and why, even when he was just watching casually.”
Audacy/WEEI photo
Middlebrooks joined CBS HQ as a baseball analyst that year, and also called college games for CBS Sports Network. While he didn’t love it at first, he soon found satisfaction in utilizing his knowledge and talking about the game again, just as Dell had predicted he would.
NESN noticed, and hired him to join its cast of studio analysts for the 2022 season. Late that season, when word broke that beloved analyst Dennis Eckersley would retire, Middlebrooks got a tryout in the booth. “I did a three-man booth with Eck and OB [current play-by-play announcer Dave O’Brien],” he says. “And it was a blast. Eck helped me a lot. He told me to be myself because they wouldn’t ask you to do this if they didn’t like you.”
Part of Middlebrooks’s charm is his penchant for poking fun at himself. (“The best part of broadcasting is that I never go ‘0-fer’ anymore,” he quips.) But O’Brien also sees what Dell recognized in him when she nudged him toward this new career. “He sees things most people wouldn’t notice,” he says. He cites an example from June, when Blue Jays pitcher Chris Bassitt, a recent nemesis of the Red Sox, recorded two quick outs to open the game.
“It looks like Bassitt is about to have his way against the Red Sox again,” O’Brien says, “but Will says, ‘There’s something up with him. He looks like he’s about to get hit. They’re going to get to him.’ And wouldn’t you know it, boom-boom-boom, the Sox knock him all over the ballpark and the game is over early. And I look at him like, ‘How did you know that?’”
Some of Middlebrooks’s prescience comes from a life spent in baseball. And some comes from preparation, the kind of homework he has to do on this Saturday before the players take the field. Already, it’s been an eventful day, with Madison and Makenzie taking in the sights of the park and playing ball on the impossibly green grass. But it’s time for Dad to lock in.
As our conversation winds down, I ask for a scouting report on Dell as a mom. Suddenly, the couple’s rapid banter becomes earnest — emotional, even.
“She is the engine of our family,” Middlebrooks says. Dell’s eyes begin to well up as he talks and she wipes away a tear. He won’t look at her, because he knows he will tear up too.
“We joke about [being] Type A,” he says. But “mentally, emotionally, professionally, I don’t know where I’d be without her. She’s so caring, and the most strong-willed person I’ve ever met. She’s a star in her job, and yet everyone else comes before her.”
He looks at her. “I should tell you this more,” he says.
And the scouting report on Will? “Whatever he is passionate about, he will give his all for that,” Dell says. “It used to be baseball. Now it’s about being a dad.”
She enlists Madison for her insights. “What are some of the things you love about Daddy?”
Madison ponders the question. “He gives me candy.” She pauses. “And money.”
“What’s your serious answer?” Middlebrooks says with a laugh.
“Ummm … a lot of things. He takes us to baseball games. And plays baseball outside with us.”
The charts will remain color-coded for the busy family, with Mom and Dad in their high-profile broadcasting careers and the kids busy with their own activities. But they are hoping to streamline. Middlebrooks and Dell are searching for their own place in Boston, for the summer months when the girls are out of school. “Maybe we’ll rent it to a Bruins player in the offseason,” he muses.
Before he heads to the booth to begin his prep, Middlebrooks makes a quick detour, heading down to the Fenway lawn for just a few more minutes with Dell and the girls.
“We want them to grow up understanding how special this is,” Dell says.
“I still walk into the stadium and still fall in love with it,” says Middlebrooks. “We want them to feel that way too. Some pretty good things happened for their parents in this place.”