{"id":560,"date":"2026-05-17T19:05:58","date_gmt":"2026-05-17T19:05:58","guid":{"rendered":"https:\/\/bostonrelocationinsider.com\/?p=560"},"modified":"2026-05-17T19:05:58","modified_gmt":"2026-05-17T19:05:58","slug":"it-wasnt-a-fling-will-middlebrooks-jenny-dell-reflect-on-their-fenway-love-story-and-being-a-media-power-couple","status":"publish","type":"post","link":"https:\/\/bostonrelocationinsider.com\/?p=560","title":{"rendered":"\u2018It wasn\u2019t a fling\u2019: Will Middlebrooks, Jenny Dell reflect on their Fenway love story and being a media power couple"},"content":{"rendered":"<article>\n<div>\n<p><span>From a third-floor suite at Fenway Park, Will Middlebrooks is scanning the gray sky as it spits rain. Midsummer Saturdays here are meant to be sun-drenched and postcard-ready, but a couple hours before the Red Sox\u2019 afternoon matchup against the Toronto Blue Jays, it seems doubtful the game will be played at all.<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=558\">\u2018That\u2019s home to me\u2019: Marcelo Mayer to practice at shortstop as Red Sox mull position change<\/a><\/p>\n<p><span>After studying the clouds for a few moments, Middlebrooks\u2009\u2014\u2009now in his fourth season as a television and radio analyst covering his former team\u2009\u2014\u2009says with a weatherman\u2019s confidence, \u201cThis is gonna clear up.\u201d<\/span><\/p>\n<p><span>His forecast will prove correct; the game will start on time. Middlebrooks\u2019s optimism is impressive, even as the truth becomes clear: Of course he\u2019s optimistic. His day\u2009\u2014\u2009his last few, really\u2009\u2014\u2009has been filled with sunshine.<\/span><\/p>\n<\/div>\n<div>\n<p><span>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.<\/span><\/p>\n<div>\n<div>\n<div><span>Get Starting Point<\/span><\/div>\n<div><span>A guide through the most important stories of the morning, delivered Monday through Friday.<\/span><\/div>\n<div>\n<div><label>Enter Email<\/label><\/p>\n<div><button>Sign Up<\/button><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<p><span>Middlebrooks\u2019s job has kept him away from their new home in Boynton Beach, Florida, too often lately. Of the Red Sox\u2019 162 games this season, he will end up being part of around 120, between NESN and WEEI, the club\u2019s flagship television and radio outlets, respectively. (<i>Globe <\/i>owner John Henry is principal owner of Fenway Sports Group, which owns the Red Sox and 80 percent of NESN.)<\/span><\/p>\n<p><span>\u201cI\u2019m in a span of being home for something like six of 50-something days,\u201d Middlebrooks says. \u201cOur careers require a lot of flexibility and sacrifice, and we both understand that because we\u2019re both in this business, but it\u2019s so hard when we\u2019re not all together.\u201d<\/span><\/p>\n<p><span>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. <\/span><\/p>\n<p><span>With Middlebrooks in Boston or on the road with the Red Sox, Dell had to handle the logistics on her own. <\/span><\/p>\n<p><span>\u201cThis one was tougher than when we moved cross-country [from Scottsdale, Arizona] in 2018,\u201d he says. \u201cWhich she also had to do alone.\u201d<\/span><\/p>\n<p><span>\u201cThis one did not go smooth,\u201d she confirms. <\/span><\/p>\n<p><span>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. <\/span><\/p>\n<p><span>For five days, home has come to Middlebrooks. <\/span><\/p>\n<p><span>There is no more fitting locale than Fenway Park for this reunion. Dell, now 39, and Middlebrooks, 37, connected here in 2012\u2009\u2014\u2009she the bright-eyed newcomer on NESN, he the Red Sox\u2019 wide-eyed rookie third baseman. It was here that, amid breathless coverage in the gossip pages\u2009\u2014\u2009and questions about the line between sports media and the teams they cover\u2009\u2014\u2009their relationship quickly blossomed into real love. <\/span><\/p>\n<p><span>This summertime visit gives their daughters a chance to further forge their own connection with Dad\u2019s workplace, and Mom\u2019s former one, and get to know the place where the early chapters of their family story were written. <\/span><\/p>\n<p><span>At one point, while the family and a reporter walk along the Dell Technologies Suites (no relation to Jenny) on the ballpark\u2019s third level, the girls point out the plaques honoring members of the Red Sox Hall of Fame. <\/span><\/p>\n<p><span>Middlebrooks smiles. \u201cThe other day, one of the girls asked me where my plaque was,\u201d he says, deploying the self-deprecation that has served him well as a broadcaster. \u201c\u2009\u2018Well, honey, you see, Daddy [only] hit 43 career home runs. .\u2009.\u2009.\u2009\u2019\u201d<\/span><\/p>\n<p><span>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.<\/span><\/p>\n<p><span><span>A<\/span><\/span><span><span>rriving at the NESN suite for an interview, Middlebrooks and Dell are dressed in what could be called their Fenway best\u2009\u2014\u2009she\u2019s 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\u2009\u2014\u2009and this reporter realizes he is in for a transcription nightmare. <\/span><\/span><\/p>\n<p><span>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. <\/span><\/p>\n<p><span>\u201cIt\u2019s a good thing that I\u2019m type A &#8230;\u201d she is saying.<\/span><\/p>\n<p><span>\u201c&#8230; She is type A. She\u2019s the organized one,\u201d he says. \u201cI grew up in baseball, where everything is taken care of for you and we\u2019re totally spoiled. She\u2019s like, <i>everything<\/i> is going to be scheduled &#8230;\u201d<\/span><\/p>\n<p><span>\u201cIt has to be,\u201d she says with a nod.<\/span><\/p>\n<p><span>\u201cIt has to be with as many moving pieces as we have.\u201d He rattles off an assortment of sports and other activities the girls are involved in.<\/span><\/p>\n<p><span>I joke that they must have a giant, complicated schedule taped to the refrigerator.<\/span><\/p>\n<p><span>Dell whips out her phone and opens up an app featuring color-coded schedules for the family. \u201cI\u2019m pink, he\u2019s green, the girls each have their own color,\u201d she says with more than a hint of pride. \u201cIt\u2019s completely organized.\u201d<\/span><\/p>\n<p><span>\u201cSo she\u2019s actually Type A-plus,\u201d Middlebrooks deadpans. <\/span><\/p>\n<p><span>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. <\/span><\/p>\n<p><span>Dell was green, and NESN delayed her debut during spring training so she could get more practice. When it became clear she wasn\u2019t quite ready for live shots, the station decided to tape her in-game segments ahead of time. Russ Kenn, the producer of NESN\u2019s 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. <\/span><\/p>\n<p><span>\u201cWhen we started with her, she had a lot to learn,\u201d says Mike Narracci, the director of NESN\u2019s Red Sox broadcasts back then. \u201cBut 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.\u201d <\/span><\/p>\n<p><span>Don Orsillo, NESN\u2019s 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. \u201cShe clicked with us right away and was a part of what we did instantly,\u201d says Orsillo, now in his 10th season of calling San Diego Padres games. \u201cShe had a similar sense of humor to ours&#8230; It felt like we had worked together for years.\u201d<\/span><\/p>\n<p><span>Dell was making her name in Boston. She didn\u2019t know it yet, but her future husband would soon arrive in the city.<\/span><\/p>\n<p><span><span>I<\/span><\/span><span><span>n May of 2012, after an injury sent Kevin Youkilis\u2009\u2014\u2009the popular but fading third baseman\u2009\u2014\u2009to 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<i> Baseball America.<\/i><\/span><\/span><\/p>\n<p><span>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. <\/span><\/p>\n<p><span>Here\u2019s one: Dell\u2019s childhood best friend was Lexi Allen\u2009\u2014 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\u2019s best friend growing up in Texarkana, Texas.<\/span><\/p>\n<p><span>When Dell started at NESN, she had intended to seek out Middlebrooks. \u201cWhen 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, \u2018I have a friend, Will Middlebrooks, he\u2019s going to be a rookie this year. He\u2019s probably just as nervous as you are.\u2019\u201d So during her first visit to the clubhouse in spring training, Dell made a beeline for his locker. <\/span><\/p>\n<p><span>\u201cI was No. 83, stuck in the corner, down by the food room,\u201d Middlebrooks recalls. \u201cI was 23, and definitely nervous.\u201d<\/span><\/p>\n<p><span>\u201cSo I walk in,\u201d Dell says, \u201cAnd David Ortiz immediately gives me a hard time about my shoes, \u2018You! New girl! What\u2019s on your feet?\u2019 So I wasn\u2019t that inconspicuous, I guess.\u201d<\/span><\/p>\n<p><span>She pauses and breaks into a big smile. \u201cWill\u2019s was the first locker I went to. Turned out to be a great decision.\u201d<\/span><\/p>\n<p><span><span>A<\/span><\/span><span><span>sked 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. <\/span><\/span><\/p>\n<p><span>\u201cWe 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,\u201d Dell says. \u201cAnd we were basically told, <i>Keep it under the radar, because you don\u2019t know if this is going to be a quick little relationship or turn into something more.<\/i>\u201d<\/span><\/p>\n<p><span>The couple tried to keep their romance under wraps during the next season, which would prove an emotional one at Fenway Park. <\/span><\/p>\n<p><span>In the aftermath of the Boston Marathon bombings in April of that year, the Red Sox played a role in the city\u2019s healing. Before the first game at Fenway after the bombings, Ortiz addressed the fans and gave the city a rallying cry that would endure. \u201cThis is our [expletive] city,\u201d he declared, \u201cand nobody is going to dictate our freedom. Stay strong.\u201d <\/span><\/p>\n<p><span>Middlebrooks, for his part, tweeted the morning after the bombings: \u201cI can\u2019t wait to put on my jersey today &#8230; I get to play for the strongest city out there. #BostonStrong.\u201d <\/span><\/p>\n<p><span>\u201cThat year, my role really turned from being the Red Sox reporter to\u2009\u2014\u2009I don\u2019t want to say a voice to help the city, but every game we had someone on [the broadcast] who was deeply affected,\u201d Dell says. <\/span><\/p>\n<p><span>\u201cIt became part of our identity that year,\u201d Middlebrooks adds. \u201cWe wanted people to be part of us, that we were all in it together.\u201d Meanwhile, on the field, the emboldened Sox\u2009\u2014\u2009a last-place team the previous season\u2009\u2014\u2009were marching to the playoffs. <\/span><\/p>\n<p><span>The quest to keep their relationship private was mostly successful, though the rumor mill did not rest all season. <i>The Boston Herald\u2019<\/i>s \u201cInside Track\u201d gossip column\u2009\u2014\u2009which referred to Dell as a \u201cbaseball babe beat reporter\u201d and \u201cbodacious brunette\u201d\u2009\u2014\u2009occasionally hinted at their connection with lines such as this one in November 2013: \u201cNESN vixen Jenny Dell and Red Sox infielder Will Middlebrooks [seen] hanging together at Howl At The Moon.\u201d<\/span><\/p>\n<p><span>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.<\/span><\/p>\n<p><span>\u201cThere were times when he was in Triple A, rehabbing an injury, and I\u2019m up with the big team, and doing reports on how he\u2019s doing in the minor leagues,\u201d she says. \u201c\u2018Well, he went 3 for 4 today with a homer, I am well aware.\u2019\u201d<\/span><\/p>\n<p><span>\u201cIt was interesting,\u201d he says, \u201cbecause especially at the beginning of a relationship, you\u2019re 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.\u201d<\/span><\/p>\n<p><span>The couple moved in together that season, knowing they couldn\u2019t be seen out in public, but also that their relationship was deepening. And, as Middlebrooks puts it, \u201cYou learn about a person real quick when you\u2019re living together, and at a ballpark together, and traveling on the road together.\u201d<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=556\">Inside the phenomenon of the Portland Hearts of Pine: \u2018This will save American soccer\u2019<\/a><\/p>\n<p><span>You find out who is Type A-plus, it\u2019s suggested.<\/span><\/p>\n<p><span>\u201cHe found who he was <i>really<\/i> about to get involved with,\u201d she says, laughing.<\/span><\/p>\n<p><span><span>T<\/span><\/span><span><span>heir efforts to keep things professional at work made for some awkward moments during the end of that season.<\/span><\/span><\/p>\n<p><span>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. <\/span><\/p>\n<p><span>\u201cI\u2019m down on the field doing all the interviews,\u201d Dell recalls, \u201cand I\u2019m bear-hugging Papi [Ortiz] and [Mike Napoli] and all the guys, and then with Will, I shook his hand.\u201d<\/span><\/p>\n<p><span>\u201cShe shook my hand,\u201d Middlebrooks repeats, shaking his head.<\/span><\/p>\n<p><span>\u201cAnd I was like, \u2018Congrats, Will!\u2019 Inside I just wanted to grab him and be like, \u2018You just won the World Series!\u2019\u201d <\/span><\/p>\n<p><span>Later, after the party moved from the locker room to a club, they weren\u2019t so subtle, at least in Narracci\u2019s recollection. <\/span><\/p>\n<p><span>\u201cWe don\u2019t recommend you date a player, obviously, and we communicate that,\u201d Narracci says. \u201cBut I didn\u2019t know they were together with my own eyes until the celebration at Game On after the win. I saw them together and was like, \u2018Oh, OK, great,\u2019 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. <\/span><\/p>\n<p><span>\u201cYou can\u2019t stop who you love and who loves you, you know?\u201d<\/span><\/p>\n<p><span><span>O<\/span><\/span><span><span>n New Year\u2019s Eve that year, Middlebrooks and Dell at last confirmed that they were together. <\/span><\/span><\/p>\n<p><span>On his Twitter account, Middlebrooks posted a picture of them together with the message, \u201cHappy New Year from us to you! Here\u2019s to a great 2014! @JennyDellNESN.\u201d <\/span><\/p>\n<p><span>It had been an unexpected Cupid who encouraged them to go public.<\/span><\/p>\n<p><span>\u201cThat was actually Jerry Remy\u2019s idea,\u201d Dell says. \u201cHe was like, \u2018Hey, you and Will are at the point now when you\u2019ve been together for at least a year. Go ahead, let people know.\u2019\u201d <\/span><\/p>\n<p><span>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\u2019s predecessors at NESN. <\/span><\/p>\n<p><span>A few weeks after Middlebrooks and Dell\u2019s announcement, Abby Chin, the Celtics sideline reporter for NBC Sports Boston, told a New Hampshire radio station: \u201cAs a woman in this business, we are constantly climbing an uphill battle when it comes to credibility,\u201d she said. \u201cSo even the slightest nick in your armor could have a much larger effect.\u2009.\u2009. Women in this business don\u2019t get three strikes, they get one.\u201d<\/span><\/p>\n<p><span>(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 <i>Globe<\/i> sports columnist Jackie MacMullan put the conundrum this way: \u201cI know when I became a journalist, you had to be objective. That was the rule&#8230; It\u2019s impossible to be objective about someone when you\u2019re in a personal relationship.\u201d )<\/span><\/p>\n<p><span>\u201cI understood the weight that it carried as a reporter,\u201d Dell says. \u201cYou don\u2019t want to be looked at a certain way. There\u2019s a lot of women in the industry that are looked at in different ways because of relationships.\u201d<\/span><\/p>\n<p><span>In January 2014, NESN management, partially in response to backlash about Dell\u2019s relationship with Middlebrooks, moved her to a studio role. <\/span><\/p>\n<p><span>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. \u201cIt wasn\u2019t a black-and-white decision, because maybe she could divorce her personal life from her professional one,\u201d Werner said at the time. \u201cBut in the end we decided it was time to move on.\u201d <\/span><\/p>\n<p><span>\u201cIt wasn\u2019t a fling,\u201d Dell says. \u201cI 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\u2019s supposed to.\u201d <\/span><\/p>\n<p><span>\u201cIt wasn\u2019t really until we got engaged,\u201d Middlebrooks says, \u201cthat people realized, <i>Wait. They really love each other.<\/i>\u201d<\/span><\/p>\n<p><span><span>D<\/span><\/span><span><span>ell 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. <\/span><\/span><\/p>\n<p><span>While Dell worked her way up the ranks at CBS Sports\u2009\u2014\u2009she 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\u2009\u2014\u2009Middlebrooks\u2019s 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\u2019d 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.<\/span><\/p>\n<p><span>\u201cIt felt like something bad happened every year,\u201d he recalls. \u201cBroke my wrist at the end of 2012, and then after that it just snowballed. Calf, finger, disc in back, two shoulder surgeries. I\u2019d play a few months, things would be going well, injuries would happen, I\u2019d come back, finish the year great, and I\u2019d get a job the next year.\u201d<\/span><\/p>\n<p><span>The news off the field was much better. On Valentine\u2019s 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\u2019 first dance was Ingrid Michaelson\u2019s version of \u201cCan\u2019t Help Falling in Love.\u201d<\/span><\/p>\n<p><span>Middlebrooks\u2019s 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. <\/span><\/p>\n<p><span>The injury happened the day after they had found out Dell was pregnant, which had been an arduous journey of its own. \u201cTwo and a half years, 524 shots, over 1,000 pills, multiple procedures, and countless tears,\u201d she wrote on social media at the time, \u201call for this moment.\u201d<\/span><\/p>\n<p><span>\u201cThe highest of the highs and the lowest of the lows,\u201d Middlebrooks recalls.<\/span><\/p>\n<p><span><span>A<\/span><\/span><span><span>fter several months of rehab, Middlebrooks was still struggling to walk. It was then that \u201cI realized I probably wasn\u2019t going to play again,\u201d 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. <\/span><\/span><\/p>\n<p><span>\u201cI was miserable,\u201d he says. \u201cIt was my identity, who I always was, and that was gone.\u201d<\/span><\/p>\n<p><span>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\u2019t 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.<\/span><\/p>\n<p><span>Besides, Dell had other ideas, along with some excellent contacts.<\/span><\/p>\n<p><span>\u201cI called CBS,\u201d she says.<\/span><\/p>\n<p><span>\u201cShe came home from CBS HQ one day in early June, and she was like, \u2018Hey, you need to give this [broadcasting] a try,\u2019\u2009\u201d says Middlebrooks. \u201c\u2009\u2018Get a haircut. Find a suit. Maybe read up on these five topics.\u2019\u2009\u201d<\/span><\/p>\n<p><span>\u201cI hadn\u2019t watched a pitch of baseball, because it broke my heart and I was still in that state. And I was like, \u2018Absolutely not.\u2019 She had already told them I was going to do it, and I was kind of pissed.\u201d<\/span><\/p>\n<p><span>\u201cHe needed to get off his\u2009\u2026,\u201d she says, smiling. \u201cSo I forced his hand. As much as he didn\u2019t 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.\u201d<\/span><\/p>\n<div>\n<div>\n<blockquote>\n<div>\n<div>\n<div> <\/div>\n<\/div>\n<div><svg><g><g><g><\/g><\/g><\/g><\/svg><\/div>\n<div>\n<div>View this post on Instagram<\/div>\n<\/div>\n<div>\n<div> <\/div>\n<div> <\/div>\n<div> <\/div>\n<\/div>\n<div> <\/div>\n<p>A post shared by Will Middlebrooks (@willmiddlebrooks_)<\/p>\n<\/div>\n<\/blockquote>\n<\/div>\n<\/div>\n<p><span><i>Audacy\/WEEI photo<\/i><\/span><\/p>\n<\/p>\n<p><span>Middlebrooks joined CBS HQ as a baseball analyst that year, and also called college games for CBS Sports Network. While he didn\u2019t 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. <\/span><\/p>\n<p><span>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. \u201cI did a three-man booth with Eck and OB [current play-by-play announcer Dave O\u2019Brien],\u201d he says. \u201cAnd it was a blast. Eck helped me a lot. He told me to be myself because they wouldn\u2019t ask you to do this if they didn\u2019t like you.\u201d<\/span><\/p>\n<p><span>Part of Middlebrooks\u2019s charm is his penchant for poking fun at himself. (\u201cThe best part of broadcasting is that I never go \u20180-fer\u2019 anymore,\u201d he quips.) But O\u2019Brien also sees what Dell recognized in him when she nudged him toward this new career. \u201cHe sees things most people wouldn\u2019t notice,\u201d 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.<\/span><\/p>\n<p><span>\u201cIt looks like Bassitt is about to have his way against the Red Sox again,\u201d O\u2019Brien says, \u201cbut Will says, \u2018There\u2019s something up with him. He looks like he\u2019s about to get hit. They\u2019re going to get to him.\u2019 And wouldn\u2019t 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, \u2018How did you know that?\u2019\u201d<\/span><\/p>\n<p><span><span>S<\/span><\/span><span><span>ome of Middlebrooks\u2019s 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\u2019s 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\u2019s time for Dad to lock in. <\/span><\/span><\/p>\n<p><span>As our conversation winds down, I ask for a scouting report on Dell as a mom. Suddenly, the couple\u2019s rapid banter becomes earnest\u2009\u2014\u2009emotional, even. <\/span><\/p>\n<p><span>\u201cShe is the engine of our family,\u201d Middlebrooks says. Dell\u2019s eyes begin to well up as he talks and she wipes away a tear. He won\u2019t look at her, because he knows he will tear up too. <\/span><\/p>\n<p><span>\u201cWe joke about [being] Type A,\u201d he says. But \u201cmentally, emotionally, professionally, I don\u2019t know where I\u2019d be without her. She\u2019s so caring, and the most strong-willed person I\u2019ve ever met. She\u2019s a star in her job, and yet everyone else comes before her.\u201d<\/span><\/p>\n<p><span>He looks at her. \u201cI should tell you this more,\u201d he says.<\/span><\/p>\n<p><span>And the scouting report on Will? \u201cWhatever he is passionate about, he will give his all for that,\u201d Dell says. \u201cIt used to be baseball. Now it\u2019s about being a dad.\u201d<\/span><\/p>\n<p><span>She enlists Madison for her insights. \u201cWhat are some of the things you love about Daddy?\u201d<\/span><\/p>\n<p><span>Madison ponders the question. \u201cHe gives me candy.\u201d She pauses. \u201cAnd money.\u201d <\/span><\/p>\n<p><span>\u201cWhat\u2019s your serious answer?\u201d Middlebrooks says with a laugh.<\/span><\/p>\n<p><span>\u201cUmmm &#8230; a lot of things. He takes us to baseball games. And plays baseball outside with us.\u201d<\/span><\/p>\n<p><span>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. \u201cMaybe we\u2019ll rent it to a Bruins player in the offseason,\u201d he muses. <\/span><\/p>\n<p><span>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. <\/span><\/p>\n<p><span>\u201cWe want them to grow up understanding how special this is,\u201d Dell says.<\/span><\/p>\n<p><span>\u201cI still walk into the stadium and still fall in love with it,\u201d says Middlebrooks. \u201cWe want them to feel that way too. Some pretty good things happened for their parents in this place.\u201d<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=554\">Don\u2019t miss a moment of the action: Sign up for Court Sense, our Celtics newsletter<\/a><\/p>\n<\/div>\n<\/article>\n","protected":false},"excerpt":{"rendered":"<p>Their relationship began as fodder for the gossip pages \u2013 and things haven\u2019t slowed down since. <\/p>\n","protected":false},"author":1,"featured_media":559,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[7],"tags":[],"class_list":["post-560","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-sport"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.6 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>\u2018It wasn\u2019t a fling\u2019: Will Middlebrooks, Jenny Dell reflect on their Fenway love story and being a media power couple - 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