How many talents can one man have? If you’re Jae Holland, the answer is ‘as many as you want.’ A born leader in the entertainment industry, the Lynn, MA native has built -and continues to build- an illustrious career in music, events, coaching, and philanthropy. BostonMan’s Elizabeth Pehota delves into the serendipitous journey with Boston’s Unsung Hero of Entertainment!

Photo courtesy of Jae Holland

IN the bustling world of professional sports, where precision, planning, and performance often dominate the conversation, Jae Holland’s story is a testament to the power of serendipity. As the Director of Fan Services & Entertainment for the Boston Red Sox, Holland’s journey is a story of success that has been not only driven by his skillset, but by chance encounters, heartfelt moments, and making the most of and growing from unexpected, fortuitous opportunities.

Growing up in Lynn, Massachusetts, Jae Holland attended Lynn Tech High School, where his love for sports and entertainment first began to take root. Yet, it wasn’t until his time at Fisher College that a serendipitous moment set the course for his remarkable career. Fisher College, a private institution nestled within Boston’s brownstones on Beacon Street, was not even on Holland’s radar initially. He had other plans for college, but financial constraints and unforeseen changes forced him to reconsider his options. Fisher College came to his high school for an on-the-spot acceptance day, and Holland never looked back.

Photo courtesy of Jae Holland

Interestingly, a friend Holland grew up with in Lynn ended up attending Fisher College as well, and they only discovered this coincidence on move-in day.

“It’s funny,” said Holland. “We grew up in the same building, but had no idea we were both going to Fisher until that day.”

It was a serendipitous sign, marking the first of many chance occurrences that would ultimately change his life.

During his time at Fisher, Holland formed meaningful relationships with the staff, including Arthur Asbury, the student registrar. Asbury’s jovial demeanor and candid conversations made a lasting impression on Holland. One day, Asbury mentioned a part-time position with the Boston Red Sox, suggesting Holland apply.

“I told him no way I was applying to work for the Red Sox,” Holland says with a laugh. “I am not a baseball fan.

Asbury, however, was persistent. He saw something in Holland—a potential that could shine at Fenway Park. He kept nudging Holland, insisting he had the personality the Red Sox were looking for. Eventually, Asbury made Holland a deal. If Holland attended a networking event at Fenway Park then Asbury would sign off on Holland’s overloaded class schedule for the semester.

Photo courtesy of Jae Holland

“To his credit, he stuck with it,” said Holland. “ I told him I would go and I am a man of my word.”

Holland arrived at Fenway Park, overwhelmed by the massive line of hopefuls stretching far past Kenmore Square. Not one to be deterred, he confidently walked past the line, acting as though he belonged.

Inside, he mingled with people, especially those wearing the Red Sox sweaters, engaging in conversation and making sure to introduce himself to everyone multiple times because he wasn’t sure who knew Asbury, and he wanted him to ensure he would sign off on his class schedule. The next day, Asbury, true to his word, signed off on Holland’s classes, and soon after, Holland received a call for an interview with the Red Sox.

Photo courtesy of Jae Holland

A lucky moment of happenstance.

Expecting a one-on-one interview, Holland was surprised to find himself in a room with more than a half-dozen casually dressed staff members. Despite his nerves, he charmed the room with his genuine enthusiasm and big personality. “I walked in and broke the ice with a joke about having a long night, “said Holland. “Everyone started laughing, and that set a positive tone for the interview.”

The interview went extremely well, and to Holland’s surprise, they weren’t testing his knowledge he had learned from watching SportsCenter. “Not one question was asked about baseball,” Holland admits. “I thought they’d want someone who knew baseball inside out, but their focus was on my personality and fit for the organization.”

This initial interview led to more meetings, volunteer work, and eventually, in early 2007, he stepped up to the plate with a part-time position as a Fenway Ambassador. His first year culminated in the Red Sox winning the World Series, an experience Holland describes as surreal.

Photo courtesy of Jae Holland

“That kicked off my journey with the Red Sox,” said Holland. “I was on a duck boat during the parade down Boylston Street, seeing my classmates and professors cheering us on. It was an unforgettable moment.”

Holland’s career with the Red Sox progressed steadily. After five and a half seasons as a Fenway Ambassador, he became full-time in August 2011. From there, he climbed the ranks within the Fan Services and Entertainment department, earning promotions from coordinator to specialist, then manager, senior manager, and finally, director in January 2022.

In his current role, Holland oversees the fan experience at Fenway Park, a responsibility he takes to heart.

“We can’t control the outcome of the game, but we can control how people feel when they walk through our gates,” Holland explains. “Our goal is to ensure that every fan has a memorable experience, whether they’re in the concourse, the seating bowl, or engaging with our staff.”

The other side of his job involves orchestrating the ballpark entertainment.

“It’s like managing 81 different award shows,” he says. “From pregame ceremonies to anthem singers and first pitches, we make sure each group feels special and properly represented.”

Photo courtesy of Jae Holland

His team prepares daily scripts and coordinates with various groups to ensure smooth operations.

“As a director, I focus not only on the present day’s events but also on what’s coming up in the next few days. It’s a balancing act, ensuring everything runs smoothly while planning ahead.”

One of Holland’s favorite memories involves a then young boy named Jordan Leandre, who was battling cancer. Back in 2007, Holland was assigned to assist Leandre and his family during a visit to the park. Leandre, known around the office and even featured in the movie Fever Pitch, was set to sing the national anthem despite his limited mobility. Holland recalls Leandre’s innocent request to run the bases after his performance. Unsure at first, Holland made it happen.

It was magical. Before Leandre even finished his last note of ‘The Star-Spangled Banner,’ he took off, and the stadium loved it.

“I’m pretty sure he thought he was Usain Bolt,” said Holland with a smile.

The crowd’s roars increased as he made his way around the bases, and became even louder as he neared home plate.

A fortunate coincidence is that the 1967 Impossible Dream Team was having a 40 year reunion at this Red Sox game, and with Leandre singing the national anthem, it was a moment of fate.

“As he’s making his way around, the 1967 team all meet him at home plate,” said Holland. “The crowd was crazy. The team picked him up and carried him off. It was so symbolic because in 1967, they carried the starting pitcher off the field. Those are the types of moments you can’t even script.”

Another standout memory for Holland is from 2022 when Fenway Park celebrated Juneteenth for the first time. As an African American man, Holland felt immense pride in this event. There were special giveaways and tributes during the game. It was a proud moment for Holland as he truly felt that Fenway had become a place that anyone, no matter their race, could belong.

Photo courtesy of Jae Holland

“Seeing that come to fruition, understanding the history that comes with it, and being able to see that night come together was so special,” said Holland. “It was a proud moment.

Holland’s career is also peppered with interactions with celebrities. Meeting Dr. Dre, for instance, was particularly memorable.

“He was promoting ‘Beats by Dre’ and was incredibly humble and down-to-earth,” Holland recalls. “Getting to hear unreleased music and knowing he actually drinks gin and juice was just a bonus.”

Photo courtesy of Jae Holland

Perhaps the most serendipitous celebrity encounter involved wrestling legend Ric Flair.

Holland is an avid wrestling fan and host of the ‘Unsanctioned Podcast’. This personal passion of his played a crucial role when Holland was tasked with surprising Red Sox Hall of Famer Dustin Pedroia, a huge Ric Flair fan, at his retirement party. Holland’s connection with Flair came through Kevin Sullivan, a former wrestling guest on his podcast.

“Planning Dustin’s retirement ceremony, we thought, ‘How do we get in contact with Ric Flair?'” Holland recalls.

Initially, they tried reaching out through WWE’s official channels, but the process was slow so that was when Holland thought to reach out to Sullivan since he is well-connected in the wrestling world. Luckily, Sullivan picked up the phone and was dedicated to making Flair come to Fenway for Pedroia’s retirement party.

“He told me, ‘Give me 15 minutes.’ Sure enough, within that time, I got a call from Flair’s wife to set it up,” said Holland.

The anticipation built as Holland coordinated the surprise, keeping it under wraps from Pedroia. “Ric Flair was honored to be asked,” Holland says. “He remembered feeling excited when he met Dustin years ago and happily agreed to be a part of his surprise.”

Photo courtesy of Jae Holland

As a lifelong Flair fan, Holland picked up Flair at the airport ahead of Pedroia’s retirement party. “Rick is someone I idolized, so I had to remind myself to be professional,” Holland laughs. “Hearing Flair’s stories about his times in Boston was incredible.”

The surprise unfolded perfectly. During Pedroia’s ceremony, the PA announcer hinted at one more surprise. “We cut to Flair, who entered through centerfield amidst some pyro,” Holland describes. “Pedroia’s reaction was priceless—he may have dropped a few F-bombs (out of excitement) in there.”

To top it off, Flair presented Pedroia with a custom World Heavyweight Championship belt, an unforgettable moment cementing their bond.

Photo courtesy of Jae Holland

Another moment of serendipity for Holland meeting his idol and his connections laying the foundation for the surprise of a lifetime.

Beyond his professional duties with the Red Sox, Jae has made a notable impact in the entertainment industry. His foray into acting began with the independent film “Surprise, Surprise,” where he showcased his talent and versatility. Initially cast in a minor role, Holland stepped up as a lead when an actor exited the project. In addition to acting, he took on multiple roles behind the scenes, earning producer and music supervisor credits. This project not only highlighted his acting skills but also demonstrated his ability to curate and promote music, reflecting his deep understanding of the entertainment landscape.

Music has always been a significant part of Holland’s life. Transitioning from an aspiring artist to a successful songwriter, he has contributed to numerous projects. His collaboration with independent R&B artists such as Nancia and Rey Royale to name a couple on their recent albums are a testament to his songwriting prowess. Hearing fans sing along to the songs he wrote, including one he performed on, brings Jae immense pride and joy. His efforts to highlight independent artists reflect his commitment to fostering a vibrant music community.

Photo courtesy of Jae Holland

“I was actually singing on one of the tracks that I wrote, and someone in the audience knew every word,” said Holland. ‘It was such a great feeling to hear them say, ‘I love that song; it’s so different for you. I never thought you’d do something like that.’ As a writer, it’s amazing to see people connect with your work and show so much appreciation. Working with Nancia on her last two projects and on Rey’s most recent project, “I Am R&B 2: The Love Chronicles have been awesome.”

He developed his on-air skills and connected with a broader audience. His current show, “The REY ROYALE Experience,” airs every Tuesday night at 9pm on the Urban Heat 98.1 FM, an iHeartRadio affiliate. Alongside co-hosts Rey Royale, Okimi, DJ Slayer and show contributor, T.R. Personified the show immerses itself in R&B culture. The show underscores Jae’s ability to entertain & educate listeners, while elevating talented artists further cementing his status as a versatile entertainer.

Holland’s dedication to promoting R&B and soul music led him to organize events at the House of Blues Foundation Room. These events provided a platform for R&B artists, addressing the scarcity of venues dedicated to the genre, and led Holland to find a new unexpected passion.

“I thought, ‘Why pay someone to host these when I can do it myself?’ said Holland. “Hosting these events opened up more opportunities, and soon people were reaching out to ask me to host their events as well.”

Photo courtesy of Jae Holland

An additional fortuitous, and well deserved, career outcome for Holland.

While Holland was speaking in front of crowds as a host, he used his confidence gained to even try his hand at stand-up comedy. His willingness to step into this challenging arena showcases his courage and versatility. Though he humbly downplays his comedic talent, his efforts to entertain in various formats are commendable.

“I think people were just being nice, but they were coming up to me to say ‘you’re very funny,’” said Holland. I like to entertain and try to add skills to this Swiss Army knife of mine.”

Balancing his responsibilities with the Red Sox and his numerous passions requires exceptional time management and dedication. Holland’s ability to juggle multiple roles—from sports executive to songwriter, radio host, and event promoter—demonstrates his commitment to excellence in all his endeavors. His journey is a testament to the power of networking, a piece of advice he fervently shares with others.

Photo courtesy of Jae Holland

“Networking is everything,” he says. “Every connection you make could be the one that changes your life.”

In a full-circle moment of serendipity, Holland is set to speak at his former high school’s commencement ceremony. Reflecting on his journey, he hopes to inspire the next generation to embrace the unexpected and seize every opportunity.

“You never know where life will take you,” Holland said. “But if you stay open to the possibilities and keep making connections, amazing things can happen.”

Photo courtesy of Jae Holland

To keep up with + stay in touch with Jae Holland, please follow x message him on Tik Tok & Instagram @TheCoso781  and/or follow his page on Facebook @Jayo City.