Secret behind how nepo baby, 27, REALLY became Pentagon's Karoline Leavitt... as ugly gossip about her 'crass' husband swirls in DC
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She first encountered her future husband at a Halloween gathering, sporting a costume of a Border Patrol officer.

During the previous election cycle, her father gained the moniker ‘Trump turncoat’ after he supported Ron DeSantis’ fleeting presidential bid.

Now, at just 27, Kingsley Wilson emerges as the surprising figurehead of Donald Trump’s revamped ‘Department of War,’ highlighting the unpredictable pathways to prominence within this administration.

As the Pentagon’s counterpart to Karoline Leavitt, the former social media executive has become the spokesperson for the world’s most formidable military force.

Nonetheless, how she acquired the position and the influence she plans to exert remain shrouded in mystery.

Married to John Wilson, a policy expert whose connections in Washington, D.C., played a pivotal role in her rise, the Pentagon’s press secretary is part of a complex power duo. The couple, who tied the knot in 2023, presents a multifaceted dynamic behind the scenes.

‘John’s connections really helped introduce her to this world in a way she hadn’t seen before,’ a source close to both told the Daily Mail. 

The same source recalls John’s reputation during his time in Representative Matt Gaetz’s office, prior to his marriage. 

His former boss confirmed to the Daily Mail that John Wilson began his career in the office as an intern and progressed to become a Legislative Counsel.

At the age of just 27, Kingsley Wilson is the unlikely face of Donald Trump's rebranded 'Department of War'

At the age of just 27, Kingsley Wilson is the unlikely face of Donald Trump’s rebranded ‘Department of War’

Wilson met her husband at a Halloween party while dressed as a Border Patrol agent and married in 2023. (Pictured at the Kennedy Center Gala on September 27)

Wilson met her husband at a Halloween party while dressed as a Border Patrol agent and married in 2023. (Pictured at the Kennedy Center Gala on September 27)

‘He regularly prepared me for the biggest hearings and debates in Congress,’ Gaetz explained.

‘He was known to get around a little bit –– had a player’s reputation before he met Kingsley,’ a former coworker told the Daily Mail. Other ex-colleagues recalled that he had a ‘crass’ demeanor.

Their relationship began in 2021.

John notably informed friends he found a catch, ‘in the movement.’

Wilson, who began dating John in 2021, herself celebrated how they met in a now–deleted tweet from October 2024: ‘3 years ago today I went to a Halloween party dressed as Border Patrol and met my husband. Be unapologetically right–wing. It will pay off.’

It has. 

Wilson is now helping lead a communications revolution that’s kicked legacy media out of the Pentagon building entirely, replacing traditional reporters with right–wing outlets.

Her pedigree didn’t hurt. 

Mystery swirls about how she landed the post – and what mark she intends to make in her tenure

Mystery swirls about how she landed the post – and what mark she intends to make in her tenure

Despite the duo's difference of opinions in presidential picks, Wilson wished her 'incredible' dad a happy Father's Day in 2023, which prompted one social media commentator to reply to the post, noting that 'just because she doesn't agree with him on a candidate doesn't mean she doesn't love her daddy'

Despite the duo’s difference of opinions in presidential picks, Wilson wished her ‘incredible’ dad a happy Father’s Day in 2023, which prompted one social media commentator to reply to the post, noting that ‘just because she doesn’t agree with him on a candidate doesn’t mean she doesn’t love her daddy’

As the Pentagon's answer to Karoline Leavitt, the former social media executive sits as the mouthpiece for the high–stakes world of military intelligence

As the Pentagon’s answer to Karoline Leavitt, the former social media executive sits as the mouthpiece for the high–stakes world of military intelligence

Wilson is the daughter of Steve Cortes, a former Trump adviser who switched teams and threw in for DeSantis early in the 2024 primary. Kingsley, meanwhile, endorsed Trump early through the DC Young Republicans, putting father and daughter on opposite sides of the Republican race.

Despite the duo’s difference of opinions in presidential picks, Wilson wished her ‘incredible’ dad a Happy Father’s day in 2023, which prompted one social media commentator to reply to the post, noting that ‘just because she doesn’t agree with him on a candidate doesn’t mean she doesn’t love her daddy.’

One former member of the DC Young Republicans dismissed her career as a ‘nepo baby’ trajectory, comparing her to Hollywood celebrities outshined by their children.

Her résumé includes a quick rise at social platform Gettr –– the Trump–aligned social media platform founded by former Trump senior advisor Jason Miller– a stint at the hardline Center for Renewing America, and serving as national committeewoman for the D.C. Young Republicans. 

Sources say her quick jump to the Department of Defense was largely driven to Gaetz. Her husband previously worked for Gaetz on Capitol Hill before also being placed in a Pentagon policy role.

‘Gaetz was the in,’ another Young Republican source explained. 

The Daily Mail reached out to Gaetz for the story, who confirmed.

‘Kingsley Wilson is an incredibly skilled communications professional. I observed her work at the Center for Renewing America with now OMB Director Russ Vought and was consistently impressed with her poise and unique ability to persuade. When she sought to serve in the Trump/Vance Administration, I gave her my highest possible recommendation, as did many others,’ Gaetz told the Daily Mail. 

Her résumé includes a quick rise at social platform Gettr –– the Trump–aligned social media platform founded by former Trump senior advisor Jason Miller– a stint at the hardline Center for Renewing America, and serving as national committeewoman for the D.C. Young Republicans

Her résumé includes a quick rise at social platform Gettr –– the Trump–aligned social media platform founded by former Trump senior advisor Jason Miller– a stint at the hardline Center for Renewing America, and serving as national committeewoman for the D.C. Young Republicans

Wilson, who began dating John in 2021, herself celebrated how they met in a now–deleted tweet from October 2024: '3 years ago today I went to a Halloween party dressed as Border Patrol and met my husband. Be unapologetically right–wing. It will pay off'

Wilson, who began dating John in 2021, herself celebrated how they met in a now–deleted tweet from October 2024: ‘3 years ago today I went to a Halloween party dressed as Border Patrol and met my husband. Be unapologetically right–wing. It will pay off’

Department of War Deputy Press Secretary Joel Valdez defended Wilson, telling the Daily Mail that the press secretary is focused on the President and Secretary’s agenda –– and that her focus is not on ‘Washington insider b*******.’

‘Any insinuation that Kingsley Wilson has advanced in her career solely due to her husband and his connections is plain wrong and insulting, particularly to those who have had the opportunity to witness her capabilities firsthand. Kingsley has earned her current position because of her talent as a communicator, her experience as a former political commentator, and in part because of her former work as a communications staffer for President Trump’s past presidential campaign – accomplishments she earned before meeting her now husband,’ Valdez said.

With the blessing and recommendations of some influential figures in the MAGA world, Kingsley jumped from online provocateur to one of the major faces of the Pentagon –– an unprecedented move for one of the most sensitive communications jobs in the world. 

‘Trump world is based far more on actual capacity than dolled up resume. Center for Renewing America was basically an administration in waiting,’ a high-level source that has worked closely with both Kingsley and John Wilson, explained.  

Her predecessors, in Trump’s first term, such as Alyssa Farah and Dana White, brought extensive resumes that included serving as press secretaries for the Vice President or as high-level staffers for the Senate Armed Services Committee before joining the Pentagon.

There are no known plans for Kingsley to hold another Pentagon briefing at this time.

She was the voice of ‘Operation Midnight Hammer’ and the administration’s ‘war’ on narco–terrorists behind the podium all but one time when the ‘new–media’ took over, and rarely does interviews with the press.

Wilson declined the Daily Mail’s request for an interview.

'Trump world is based far more on actual capacity than dolled up resume. Center for Renewing America was basically an administration in waiting,' a high-level source that has worked closely with both Kingsley and John Wilson, explained

‘Trump world is based far more on actual capacity than dolled up resume. Center for Renewing America was basically an administration in waiting,’ a high-level source that has worked closely with both Kingsley and John Wilson, explained

But critics say she’s no Leavitt, the White House press secretary who commands a room.

‘Karoline… you know those people who, when they are in the room, demand attention? I wouldn’t say that Kingsley does,’ said a Pentagon new media source. It’s very recorded. It’s very performed. You can tell she has been prepping for the past five hours, literally just reading talking points.’

A longtime DC Young Republicans member was even more blunt: ‘If I asked 20 random staffers who Kingsley is, they’d be like, who is that?’

A former White House aide tells the Daily Mail that the opinions on Kingsley’s performance are ‘mixed.’ 

The fear is that Wilson, insulated from tough questioning after the Pentagon purged traditional reporters, might crumble under real pressure.

‘I feel like she could really get destroyed up there at that podium if the real hard–hitting journalists were there,’ the Pentagon source added. ‘There are no off–the–cuff reactions. There’s no humanity in the way she speaks.’

Jordan Conradson, a Gateway Pundit reporter now covering the Pentagon, defended her: ‘I think Kingsley is great. I think she’s very intelligent. She has a good grasp on what’s going on, and she’s able to convey the messaging very well.’

He praised the administration for ‘propping up younger voices.’

Pentagon Spokesperson Kingsley Wilson posing with colleagues and friends in red white and blue

Pentagon Spokesperson Kingsley Wilson posing with colleagues and friends in red white and blue

Former White House Press Secretary Sean Spicer tells the Daily Mail that he believes Kingsley has a bright future ahead of her in the Republican sphere.

‘Kingsley literally grew up in the MAGA movement and is one of the most promising future leaders of it. She has been a key part of spreading the president’s policies and achievements to new audiences of Americans,’ Spicer said. 

Laura Loomer, a member of the Pentagon’s new media and Trump’s self-described ‘chief loyalty enforcer,’ told the Daily Mail she ‘plays it safe.’

Wilson has scrubbed her digital footprint since taking the role, deleting posts that reportedly ranged from questioning US involvement in conflicts abroad to promoting anti–Semitic conspiracy theories on X.

‘She’s kind of like a ghost on everything now,’ one source said. ‘I guess that’s because she doesn’t want anyone to dig anything up in her forward–facing role.’

Privately, those who know her describe Wilson as ‘godly’ and ‘kind,’ someone who ‘always speaks to you with intention.’

‘I’ve always gotten the impression from her that she was very much like, wants to be a mom and a wife,’ a source friends with Kingsley said. ‘I’ve never really gotten the impression that she wanted to be in that front–facing type of role.’

Yet Pentagon insiders say she’s accessible – to the right people. ‘We have access to them. I think they shared their number with everybody,’ Conradson said. ‘Whenever I need something, really, I just shoot them texts.’

From her stance on kinetic strikes to freezing out ‘legacy media gatekeepers,’ Wilson is making clear the old rules are dead.

And as she predicted in that deleted Halloween post, being ‘unapologetically right–wing’ has paid off.

‘There is no doubt that Mrs. Wilson is always prepared, uniquely qualified, and completely endorsed by myself and Secretary Hegseth to communicate our message to the American people,’ Chief Pentagon Spokesman Sean Parnell told the Daily Mail in response to the story.

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