The internet remains fixated on the age gap between White House Press Secretary Karoline Leavitt and her 60-year-old husband Nicholas Riccio, whose deep ties to Donald Trump’s political circle date back long before Leavitt entered the picture in 2022.

Riccio was no political novice when they met—but rather a prominent real estate developer and influential figure in conservative circles, known for backing Republican politics with both money and property.

Riccio grew up as one of four kids raised by his parents, Marilyn and Anthony, who divorced when he was young. He would end up homeless by 18 and living on the streets, seeking support from friends. He lived in his car while attending Plymouth State University to be able to afford tuition. He has often credited his mom for inspiring him to pursue his real estate dreams.

His humble beginnings were a far cry from the political and financial circles he would later navigate with ease.

Long before their romance began making headlines, Riccio had solidified his reputation as a dedicated Trump supporter, seamlessly blending luxury hospitality with political influence to push forward the MAGA agenda.

That dedication became crystal clear in 2019 when Riccio hosted a high-profile Women for Trump event at not one, but two of his upscale properties in Hampton Beach.

Co-organized by the Republican National Committee, the event was more than a political gesture—it was a full campaign investment. Riccio opened his beach cottage and checkbook to support Trump’s reelection.

On M Street in Hampton, nearly 80 MAGA-clad Republican women from across the Northeast filled the space. Some traveled as far as Boston to attend.

Led by Hampton Selectman Regina Barnes and Denise Katz, the event combined elegance with political power. Guests enjoyed a catered buffet and a “Trump 2020” cake, symbolizing their shared purpose.

Yet the event was more than just a dinner party with campaign swag. It doubled as a message platform.

Female attendees sang praises of Trump’s economic policies, noting record-low unemployment for women and a reported drop of 600,000 women living in poverty. These talking points, echoed throughout Riccio’s venue, signaled his early embrace of the narratives that would become central to the Trump campaign’s playbook. Riccio wasn’t just along for the ride — he was offering the keys to the building.

His political engagement didn’t stop with Trump.

In 2005, Riccio had a memorable encounter with President George W. Bush at the Pease International Tradeport, Nicki Swift reports. The two reportedly bonded over their mutual interest in professional sports franchise ownership.

It was three years after that pivotal Women for Trump event that Riccio met Leavitt at a political gathering hosted by a mutual friend. What began as a working relationship — with Riccio joining the finance committee for her 2022 congressional campaign in New Hampshire — soon evolved into romance. Their connection grew rapidly.

In July 2024, the couple welcomed their son, Nicholas Robert, and by January 2025, they had married at the posh Wentworth By The Sea Country Club — just days before Donald Trump’s second inauguration.

Back in April when Leavitt recently shared never-before-seen photos from their wedding, social media lit up — not just over the lavish celebration, but over Riccio’s age.

Critics often flood her posts with comments about her “grandpa” husband, especially after she began sharing images of Riccio holding their infant son at the White House, though she was accused of deleting negative comments.

But that doesn’t stop the commentary on other social media platforms. “Y’all should feel bad for Karoline’s husband Nicholas because he will never know if she’s “happy “ with him without him wondering if she’s lying to his face,” wrote one person on X.

Another asked, “How creepy is it that a grown man old enough to be her dad is Karoline Leavitt’s husband?”

Taking a swipe directly at her husband’s age, a third said, “Hey Karoline where is the no tax on Social Security? It should matter to you, won’t be long and your husband will be eligible.”

During a recent interview on “The Megyn Kelly Show,” Leavitt addressed the backlash, saying her husband got “more than he bargained for” when their whirlwind romance turned into full-blown political spectacle.

“I say, ‘I walked into your life and it’s been a circus ever since,” she stated affectionately describing their life together — juggling a new baby and a high-profile job.

Amid all the noise, Riccio’s support for Trump seems to remain unchanged.

While the public dissects their age difference and newfound visibility, it’s important to remember that Riccio wasn’t pulled into the MAGA world by his 27-year-old wife — he helped build the foundation for it. His relationship with Leavitt may have added headlines, but his loyalty to the conservative movement runs much deeper, rooted in years of political activism and strategic influence long before love entered the equation.