How Trump’s Press Secretary Karoline Leavitt’s Husband Overcame Homelessness To Build Multimillion-Dollar Real Estate Empire

President Donald Trump‘s White House press secretary, 27-year-old Karoline Leavitt, made history when she became the youngest person ever to hold the role—and she couldn’t have done it without the help of her husband, Nicholas Riccio, who is 32 years her senior.

The mom of one captured the world’s attention when she made her debut in the briefing room in Washington, D.C., on Jan. 28, quickly impressing viewers with her maturity and confidence in front of the camera.

As Leavitt has already learned, standing in the spotlight on the world’s political stage has its drawbacks—namely, the furious scrutiny and criticism she has been subject to since taking on the role.

But the communications expert is no stranger to holding her own in the face of pressure, having begun her career as an intern at Fox News before later running for Congress at the age of 25.

Her bid for a seat in the U.S. House of Representatives as the Republican nominee in New Hampshire‘s 1st District ultimately failed, but it certainly helped to thrust Leavitt into the conversation as far as conservative politics are concerned. It also drew new interest in her personal life—namely, her marriage to real estate mogul and New Hampshire local Riccio, 59.

When asked about her spouse in the past, Leavitt has made clear that he is incredibly private and doesn’t like to use social media.

But while Riccio may not be a star in his own right, he is something of a local legend in New Hampshire, where he has built up a multimillion-dollar property portfolio—fulfilling a childhood dream in the process.

However, while he now enjoys a life of privilege, Riccio—who has a net worth of $6 million, according to Distractify—did not achieve his success easily.

The 59-year-old was raised in New Hampshire by his parents, Anthony and Marilyn, who divorced when he was just a young child.

Riccio hopped between homes following their separation, until he ended up living on the streets at the age of 18.

“When I was 19 or 20, I would call my buddies to go over [to] their houses to watch a game just so I could take a shower,” he previously revealed to The Portsmouth Herald.

Riccio put himself through college by stocking shelves at a grocery store and borrowing money, eventually graduating from Plymouth State University.

It was then that his interest in real estate was first fueled.

The businessman—who often opted to sleep in his car when he couldn’t afford to pay rent—took a real estate course in 1990 and fell in love with the building world. He opted to turn his interests to New Hampshire’s Hampton Beach when he realized how many properties in the area were in desperate need of rejuvenation.

He recalled to the Sunday Herald in 2005 that he and his mother were out for a drive in Hampton Beach when they came across M Street, a long stretch of properties that had fallen into a state of severe disrepair over the years—leading to some of the structures being condemned.

Riccio knew almost immediately that he wanted to make the street his legacy—but without the funds to buy up the entire street straight away, he had to start small.

He pushed his finances and managed to pull together enough money to buy just one of the buildings. And thus began his real estate portfolio.

According to property records, there are currently 10 homes registered under his company’s LLC, with nine of them in New Hampshire and one in West Virginia.

The homes were all built in the late 1900s and cost Riccio anywhere from $5,500 to $400,000.

In 2023, Riccio’s New Hampshire property made headlines when it erupted into flames. The cause of the fire was never determined; however, it was reported that the property suffered extreme water and fire damage.

According to Riccio’s company website, Nautical Beach Properties aims to help guests “enjoy” the sunshine and sparkling water nearby.

“Make yourself comfortable at the Nautical Beach Properties. Sit outside in the afternoon sun and enjoy the sunset. We are a short walk to the sandy beach and boardwalk activities. Come enjoy our friendly hospitality and more. Located close to everything you need for vacationing.

“Enjoy morning walks on the beach, sunset cruises, a wide variety of restaurants, miniature golf, water slides, and several arcades for fun the whole family can enjoy. At Hampton Harbor, just down the street, you can charter boats for whale watching and deep sea fishing.

“Hampton Beach offers a variety of nightly entertainment at the Sea Shell Stage with fireworks every Wednesday night. Lots of great shopping with souvenirs, beach wear, and other necessities and groceries,” the website reads.

Riccio currently has a number of properties and rooms up for rent. A one-bedroom waterfront room will cost guests $139 per night, while a beach house will run them around $154 a night.

Although it is unclear when Riccio and Leavitt started dating, it’s believed that the pair met through a mutual friend at a political event.

Leavitt—who worked in the previous Trump White House, where she was a member of then-Press Secretary Kayleigh McEnany‘s team—previously revealed that her husband is the “opposite” of her and is an “introvert.”

“He doesn’t have social media and he’s an introvert (complete opposite of me),” she has explained.

“I respect his privacy on here – but he’s my number one fan, the best dad, and just the best man I’ve ever met.” 

In 2022, Riccio even helped fund Leavitt’s campaign for a seat in the U.S. House of Representatives, which she ultimately lost.

The following year, the couple went Instagram-official when Leavitt posted a flick of Riccio proposing to her, alongside the caption: “I get to marry the man of my dreams. I feel SO overwhelmingly BLESSED. Thank you God.”

They went on to welcome a son on July 10, 2024, with Leavitt calling it the “best moment of her life.”

“It’s true when they say there’s nothing comparable to the love you feel for your child,” she wrote on Instagram at the time.

“My heart has grown bigger than I ever imagined possible. Babies are the ultimate blessing and I’m bursting with gratitude for our beautiful, happy, healthy boy.”

Just weeks before she stepped behind the podium as the White House press secretary, Leavitt revealed she was looking forward to heading back into the White House but admitted she was “nervous” about missing moments with her son.

She took to Instagram to lift the lid on the woes she was battling ahead of her new role, revealing that she was “praying” about the situation.

One follower questioned: “Do you worry about the demands of the job and missing out on moments with your son?” 

Leavitt replied: “Yes. I literally pray about this everyday. It’s very difficult but it’s also all I know. 

“I went back to work just days after giving birth. I have learned to multi-task and prioritize my time. 

“I’m also grateful to have an amazing husband and family who help me. Couldn’t do it without them.

“I remind myself this job is temporary, it’s the opportunity of a lifetime, and I know one day he will be proud of his mama.” 

Leavitt also shared a glimpse into what it was like working for Trump and how she was handling her upcoming move.

“We are getting ready to move. I lived in D.C. and worked in the White House during President Trump’s first time so I know the city well, and looking forward to going back,” she wrote.