Startled by Karoline Leavitt’s background as an older husband, but what makes everyone appreciate the most is the reason he chose Karoline Leavitt to be his wife.

In a stunning turn that captured headlines worldwide, 27-year-old Karoline Leavitt, President Donald Trump’s historic pick for White House Press Secretary, didn’t just shatter political records—she also shattered societal expectations with her bold, unconventional love story.

Why He Chose Her: The Quiet, Devastating Truth Behind Karoline Leavitt’s Marriage to a Man 32 Years Older—and Why It’s Making America Rethink Everything

The world saw the photo.
A 27-year-old political rising star—Karoline Leavitt—beaming, ring raised, announcing her engagement to a man few recognized.

The headlines focused on the age gap.
The memes came fast.
And the questions were louder than the applause:

“She’s 27. He’s 59. What could they possibly have in common?”
“Is this power? Money? Convenience?”

But there’s something no one asked—something that, until now, remained behind closed doors and under layers of grief, shame, and private pain:

What did Nicholas Riccio see in her that made him choose to love again—after decades of not letting anyone get close?

A Man Who Had Nothing—Until He Built Everything Alone

Before the real estate.
Before the 10 homes.
Before the black SUV and the Hampton Beach empire…

There was a boy sleeping in a car behind a liquor store.

Nicholas Riccio was 18 when he ran out of couches to sleep on.

After a messy parental divorce and years of instability, he found himself calling friends not to hang out—but to use their showers.

He stocked shelves at night.
Ate canned soup with the label half-peeled off.
Learned early that the world rarely gives second chances—and never gives them for free.

He worked. Alone. Always alone.

“I stopped believing people stayed,” Riccio once told a friend. “So I stopped letting them try.”

Love? That Door Closed Decades Ago

By 35, Riccio had made his first million.

By 40, he owned properties up and down the New Hampshire coast.

But by 50, he still ate dinner alone.

The few women he dated described him as generous—but unreachable.

One ex put it this way:

“He never let me in. It’s like he was always waiting for me to leave, so he beat me to it.”

He never married.
Never had children.
Didn’t attend weddings.
Avoided funerals.

“It’s easier when no one needs you,” he once said. “And safer when you don’t need them back.”

And Then Came Karoline

They met in a room full of donors.
She wasn’t even supposed to be there.

Fresh off a failed congressional bid, Leavitt was 25, sharp-tongued, and out of options.

Riccio saw her speak from across the room.
Not about herself—but about why people give up too early.

She wasn’t polished.
She was pissed.
And Riccio felt something snap inside his carefully built shell.

“She didn’t just remind me of who I used to be,” he later said. “She reminded me of who I stopped trying to be.”

He introduced himself quietly.
She said she knew who he was.
He didn’t believe her—until she quoted one of his rental ads… word for word.

She Saw the Man, Not the Armor

Karoline Leavitt didn’t fall for the money.

She didn’t need rescuing.

What she saw in Riccio was rarer than success.

She saw stillness. Boundaries. A man who didn’t need to be the star of the room—but would defend the person he loved like hell.

And Riccio, for the first time in 30 years, let someone see the scar tissue.

He told her about the fire.
The deal he lost in 2009 that nearly ruined him.
The night he almost sold everything and disappeared.
The friend he couldn’t save from addiction.
The brother who stopped calling.

She didn’t look away.

She stayed.

“She Wasn’t What I Wanted—She Was What I Didn’t Know I Needed”

Riccio had lived half a life in solitude—by design.

He didn’t believe in lasting connection.

Until one night, as they walked the Hampton boardwalk, Karoline said:

“You don’t have to be strong with me. I know what it’s like to stand in rooms where you’re not supposed to belong.”

And in that moment, he realized she wasn’t looking for a mentor, a backer, or a father figure.

She was looking for a witness.

“I didn’t want to be admired,” he said. “I wanted to be chosen. And she chose me—without conditions.”

Why He Married Her—Even Knowing What the World Would Say

When Riccio proposed in 2023, he did it privately.

No cameras. No yacht. Just a rented cabin, a single ring box, and a handwritten note that read:

“Thank you for seeing me when no one else did.”

They posted the photo a week later.
The backlash was instant.

“Gold digger.”
“Daddy issues.”
“What is this, Succession?”

But Riccio didn’t flinch.

Because he knew: She’d seen the parts of him no one ever asked about.

The Son That Made Him Believe in Legacy Again

When their son was born in July 2024, Riccio was 58.

He said he was terrified.
Too old. Too scarred. Too late.

But Karoline told him:

“You weren’t too late for me. And you won’t be too late for him.”

Today, Riccio takes his son to the beach every Sunday.
They don’t talk politics.
They collect shells.

“You get to rewrite everything,” he said. “No one tells you that. But you do.”

Conclusion: The Answer Isn’t Her Age—It’s His Healing

So why did he choose her?

Because after 30 years of surviving, he finally met someone who saw past the defenses and loved what was left.

Because she wasn’t scared of his quiet.
Because she didn’t need his money.
Because she held his grief like it was something sacred, not something shameful.

Because when you’ve lived a life assuming people leave—the bravest thing you can do is believe someone who promises to stay.

 

More details about both of their lives

 

President Donald Trump’s White House press secretary, Karoline Leavitt, has become a superstar in the political realm—however, her husband boasts his own very impressive career in real estate.(karolineleavitt/Instagram)

The mom of one captured the world’s attention when she made her debut in the briefing room on Jan. 28, quickly impressing viewers with her maturity.(karolineleavitt/Instagram)

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.

In addition to her accomplished resume, Leavitt’s sophisticated attitude can also be credited to her 59-year-old spouse, who has been thrust into the public eye as his wife makes waves in her new position. (karolineleavitt/Instagram)

Although Riccio is an ultraprivate man, he has grown accustomed to a lavish lifestyle as he is the manager of multimillion-dollar real estate company, Riccio Enterprises LLC, a subsidiary of Nautical Beach Properties.(karolineleavitt/Instagram)

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.”

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

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

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.

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.

Leavitt and Riccio went on to welcome a son on July 10, 2024, with Leavitt calling it the ‘best moment of her life.’ (karolineleavitt/Instagram)

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.(karolineleavitt/Instagram)

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.