Jenny Dell on her ‘blessing,’ her best friend, and her time in Boston

Dell and Will Middlebrooks are expecting their baby girl to arrive in October.

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Will Middlebrooks and Jenny Dell are expecting their first child. –Twitter

Jenny Dell and Will Middlebrooks are expecting their baby girl to arrive in October. They’ve narrowed down a short list of names for the image on the ultrasound waving back, but plan to keep the final choice between the two of them until the day she’s born. It’s a small measure of privacy for a couple who’ve chosen to share their story with the world.

In May, Dell tweeted a picture of two pink shoes and a baseball, letting her 142,000 followers know that after “two and a half years, 524 shots, over 1,000 pills, multiple procedures, and countless tears,” she was pregnant. The responses soon flooded in from around the country and beyond.


“Thank you for publicly talking about this.”

“I had a similar journey.”

“My five-year-old is from IVF.”

Dell and Middlebrooks decided to go public with their experience because they wanted to get the word out about infertility. The stigma attached to the subject — especially talking openly about it — means that it’s rarely discussed by two such high-profile figures.

“It’s not a bad thing,” Dell told “Thankfully, there’s modern medicine that’s able to help out with having babies. It’s a long journey and it’s a painful one and a stressful one, but the fact that we were able to get to the end of it and now be pregnant with a beautiful little girl — it’s a blessing.”

Dell, a CBS sideline reporter who became a fan favorite during the two years she spent at NESN, knew from the beginning that she wanted to put their story out there for friends, family, and fans. She hoped to erase some of the stigma by sparking conversations about how common infertility is and how tough in vitro fertilization can be.

Middlebrooks, who played third base for the Red Sox from 2012-14 and now plies his trade for the Philadelphia Phillies, was a bit more hesitant. He wanted to make sure they shared their story in the most respectful way. So the couple sat down and crafted exactly what they wanted to say, wording it so the message conveyed something close to their hearts but carefully considered those who hadn’t been blessed with a child.


Once the message was posted, they read every single response. Now Dell and Middlebrooks are in the process of going through and responding to each one, thanking the well wishers and talking to those who replied with stories about their own journeys.

“You know, it’s so easy on social media to look at someone’s pictures or someone’s life and think, ‘Oh, they have it all. Their lives are so perfect. They’re in a happy marriage and they have these fun careers,’” Dell said. “But people never post about the struggle. People never post about the tough times in life. So we were able to share our story and I think a lot of people were able to relate to us.”

The journey

Jenny Dell Will Middlebrooks
Jenny Dell and Will Middlebrooks married on Valentine’s Day in 2016. —Courtesy of Jenny Dell

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On Valentine’s Day 2016, Dell and Middlebrooks tied the knot in Scottsdale, Ariz., their adopted home. They settled in the city after Middlebrooks was traded by the Red Sox, the team that drafted him out of high school, to the Padres. San Diego’s spring training was in Scottsdale, and they quickly realized the Southwest climes made perfect sense as a base for the winter months.

The couple started trying to get pregnant right away, to no avail. Late that year, they visited a fertility clinic for the first time to ensure it was possible for them to conceive. To their relief, everything looked normal. Still, Dell and Middlebrooks went through two failed rounds of IUIs before turning to IVF in 2017.

The IVF treatment demands a series of shots, which for her began in October — smack dab in the middle of football season. The NFL schedule had Dell, who traded the diamond for the gridiron when she left Boston, traveling the country with a bag of medicine and a bag of needles. The precise routine the shots required meant she sometimes had to run off the field during the second quarter, administer the shots, and run back to the sideline like nothing ever happened.


On the road, she had her “amazing” CBS crew. At home, she had Will.

Middlebrooks “went above and beyond,” Dell said, administering her shots when they were together and never missing a doctor’s appointment. She noted the process isn’t easy for the husband, either.

“Obviously the wife is the one dealing with the brunt of it just because she’s the one physically going through the shots and the appointments and the work and all that craziness — he’s been the most supportive, loving husband and I couldn’t be more grateful for the way that he’s handled this whole journey. I know he’s going to make the best dad,” Dell said.

Middlebrooks learned he’d need that Rookie Dad t-shirt, when, in February, Dell found out she was pregant after her first embryo transfer try. All the shots, the pills, the sideline sprints and heartbreaking frustrations — worth it in an instant.

Two weeks later, Dell headed home to Connecticut to tell her family the good news. She stopped on the way at her alma mater, UMass Amherst, for a guest speaker role at a symposium and a slice of chicken quesadilla pizza at Antonio’s, an institution in the college town. As she drove, Dell called her father, who kept the Phillies spring training game in Florida playing on the radio in the background while they talked. Then the line went silent.


“Oh, honey.”

“Dad — what is it?”

“Oh, no.”

Middlebrooks had collided with a teammate underneath a pop fly. Dell’s father switched on his television to see the full extent of the injury. When he did, he told his daughter she needed to get back to Florida as soon as possible. Middlebrooks was carted off the field clutching a gruesome broken leg, his 2018 season over before it ever began.

So Dell did the unthinkable — turned the car around sans slice — and drove straight to Bradley Airport in Hartford, where she caught the next flight south. One of the Phillies’ wives picked her up from the airport in Tampa and took her home to Clearwater. Middlebrooks was waiting on the couch, cocooned in a giant cast.

The roles were reversed.

“As a wife, you want to fix things and make things good for the people around you, especially your husband, and it just broke my heart to see him there in pain, knowing there was nothing I could do,” Dell said.

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CBS sideline reporter Jenny Dell in the second half of a 2014 NFL game between the New England Patriots and Miami Dolphins. —AP Photo/Charles Krupa

The former Red Sox infielder has been dogged by injuries in recent years. His broken leg was particularly painful because it came at the very beginning of a season Middlebrooks started preparing for hours after the previous one ended. The couple skipped any offseason vacations so he could focus on the trainer’s room and the batting cage, then had those hours washed down the drain by a freak accident.

The 29-year-old has played for the Padres, Milwaukee Brewers, Texas Rangers, and now the Phillies since he lifted the World Series trophy with Boston in 2013. He’s set on returning to the field this year. So is his wife, who plans on working a couple football games early in the season, having her child, and returning to action for a few more at the end.

Dell said they’ve both gone through plenty of ups and downs personally and professionally since leaving Boston, but the couple always ends up on the same page.

“It would be really hard to be with someone whose life is perfect all the time and you’re struggling inside. They’re trying to help you and you’re like, ‘Okay, you don’t get it.’ But I can look at Will and say, ‘Okay, you get it,'” Dell laughed.

The friend

One night, as Middlebrooks administered Dell’s shot, she asked her husband to sing a song. He asked what she wanted to hear, but before he could launch into verse, his patient began sobbing for no discernible reason.

“Why are you crying?” Middlebrooks asked.

“I don’t know!” Dell responded.

“Are you crying because I didn’t start singing right away?”

“I don’t know!”

After a night like that, Dell said, it was nice to talk to someone who could relate to the experience. That’s why she decided to join a Facebook support group for those going through IVF. She posted in the group, sharing her own transfer date in the hopes of finding someone on the similar schedule. A woman from Washington answered her call. Within two messages, Dell had found the best friend she never knew she needed.

To this day, Dell and that woman, Claire Edwards, have never met in person, but Dell said they’re as close as sisters. They started off messaging back-and-forth on Facebook. After that conversation became a non-stop stream that showed no signs of abating, Middlebrooks suggested they exchange phone numbers. They’ve been in constant contact ever since.

The woman talked about dealing with everything from shots to husbands to restaurants that ran out of macaroni and cheese (and elicited more tears). Dell said that it was a blessing to have someone who understood the pain and hormones, as well as the stress the process puts on your body and relationships.

“It was a great, vast, crazy whirlwind of emotions that you’re going through,” she said. “They always say that women who are pregnant are hormonal, which we are, but then you add IVF into that and it’s like a whole new ballgame.”

Edwards was by her side through it all. Now, they’re both expecting. Edwards recently received the same good news as Dell and Middlebrooks had a couple months before. The moment she put the phone down, she texted her friend from Facebook.

Dell prefaced what happened next with, “First of all, I’m a very emotional person.”

She had never cried so hard for someone she hadn’t met. Middlebrooks was concerned by the sudden burst of tears, but once he found out their cause, he immediately understood. Although he had never even talked to Edwards, he knew how much their bond meant to the two of them. When both the babies are old enough, the two budding families will take a vacation together.

“You know those friends that you can go years without talking to, and when you see them it’s like no time has passed?” Dell asked. “I have a feeling that it’s going to be similar to that — even though we’ve never actually met.”

The city

When Dell first posted in that support group, it never crossed her mind that people in it might know her or Middlebrooks. She told the group right away when she found out she was pregnant in February. She didn’t tell the rest of the world until May. Somehow, in between, the news never escaped a group with 22,000 members.

Many of the women reached out after her announcement in May.

“Red Sox Nation loves you.”

“We were following this journey the whole way.”

“We’re so excited for you and Will.”

Dell thanked them all for not saying a word about the news before she did. The Red Sox Nation nod and the numerous local fans who sent their congratulations reminded the couple of the passion Boston fans have for their sports teams. It’s been four years since Dell and NESN parted ways and Middlebrooks was traded to San Diego. They’ve been ‘blown away’ by the continued support.

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Will Middlebrooks and Jenny Dell in Boston in 2014. —Bill Brett for

For Dell, a Connecticut native, the sideline reporter job with the Red Sox was her first time working live television. She described the “overwhelming” experience of being thrust into the limelight — “I had no idea what I was in for” — but she eventually settled into the role, with help from the support system behind her and Don Orsillo and Jerry Remy in the broadcast booth above.

Dell left the network in 2014 after it became known that she was dating Middlebrooks. The relationship was the worst-kept secret in town for months beforehand, but it wasn’t until Dell went public with the news that the network removed her from Red Sox broadcasts to avoid a potential conflict of interest.

The reaction in Boston was primarily one of support from the fans and the local media, but the national media’s coverage of the situation had a markedly different tone.

“Will was getting high-fives from everyone and I was getting called names somehow,” Dell said. “That’s just the way it goes.”

She remains friends with many of the women whose husbands were on the team. When she announced her pregnancy, one of the first people to congratulate her was Erin Bradley, Jackie Bradley Jr.’s wife. There’s a bond between the players in Boston, of course, but there’s also a special one among the wives, Dell said.

Now, as Dell and Middlebrooks contemplate whether to stay near their network of friends — the “little Arizona family” — in Scottsdale or move closer to their real families in New England or Texas, she didn’t rule out a return to the city where they fell in love. Either way, Baby Girl Middlebrooks will be “really loved wherever she is.”

And who will that October arrival be cheering for the next time the pennant race draws to a close?

“I feel like she has to be a Red Sox fan,” Dell said. “I mean, that’s where it all began, right? Without the Red Sox, Will and I would never have happened and she would be nowhere in existence. I guess technically we have to support whatever team Will’s playing for — but I’m hoping this little girl knows that her true roots belong with the Red Sox.”