Tiffany Trump & Don Trump Jr’s ex-wife tried to date their Secret Service agents

Republican National Convention - Day 4

There have been numerous fictional accounts romanticizing the relationships between famous women and their bodyguards. Those stories are based on a real thing – a number of royal women and celebrity women have fallen for their bodyguards or security guards, often to disastrous results. I always thought that Secret Service agents were above that. Like, the Secret Service is so difficult to get into and so heavily monitored, especially the agents protecting the First Family. So I’m a bit surprised that there are now stories about how Tiffany Trump and Vanessa Trump possibly got “too close” to Secret Service agents on their details. Who was spilling those details and how close did they get?

Tiffany and Vanessa Trump had eyebrow-raising relationships with the Secret Service agents protecting their family while Donald Trump was in the White House, a new book claims. The upcoming Zero Fail: The Rise and Fall of the Secret Service, by Pulitzer Prize-winning Washington Post reporter Carol Leonnig, describes how former President Trump’s youngest daughter and Donald Trump Jr.’s now-ex-wife both became “inappropriately — and perhaps dangerously — close” to members of the security detail. (A spokeswoman for Tiffany denies this.)

The Guardian and The Washington Post obtained advanced copies of Leonnig’s book, which is scheduled to be published on May 18. According to The Guardian’s description, Leonnig cites Secret Service agents to report that Vanessa had “started dating one of the agents who had been assigned to her family.”

It’s not clear when that alleged relationship began. Vanessa filed for divorce from Don Jr., both 43, in March 2018. Sources at the time told PEOPLE that the couple had weathered reports of his affair with a Celebrity Apprentice contestant years earlier but that, while their union recovered as they subsequently had more children, the relationship was in trouble long before the split.

According to Leonnig’s book, Tiffany sparked her own connection with a Secret Service agent with whom she “began spending an unusual amount of time alone” after a breakup. Agency officials “became concerned at how close Tiffany appeared to be getting to the tall, dark and handsome agent,” Leonnig writes, according to The Guardian and the Post. The agent was reassigned, though both he and Tiffany said there was no inappropriate relationship. It is unclear when this episode unfolded during the Trump presidency.

Asked for comment about Leonnig’s book and her reporting on Tiffany and Vanessa, a Secret Service spokesperson said: “The U.S. Secret Service is aware of an upcoming book which re-hashes past challenges the agency overcame and evolved from. Now and throughout its 156 year history, the agency’s skilled workforce is dedicated to the successful execution of its critical protective and investigative missions.”

A spokeswoman for Tiffany told the Post her “experience with the Secret Service was entirely professional” and that claims otherwise were “nothing more than gossip.” (Tiffany and Vanessa did not respond to calls and texts from PEOPLE.) Tiffany has been dating Michael Boulos since 2019. The couple announced their engagement the day before President Trump left office in January.

[From People]

“… Which re-hashes past challenges the agency overcame and evolved from…” Sounds like the Secret Service is confirming that their agents got too close to their protectees? I also kind of dislike how they’re making this all about the women. Yes, Vanessa and Tiffany should have been more respectful of the professional situation and they should have kept their hands to themselves. But it sounds like Vanessa’s Secret Service agent was into it and Tiffany’s agent was… not. And he probably got asked for a reassignment. Poor Tiffany, lol. It also sounds like the Trump women were the only ones in recent history to not understand professional boundaries. Shocking!

PS… I bet Melania was trying to get close to some of her agents too, don’t you think?

Republican National Convention - Day 2

2018 White House Easter Egg Roll

Photos courtesy of Avalon Red.

You can follow any responses to this entry through the RSS 2.0 feed.

59 Responses to “Tiffany Trump & Don Trump Jr’s ex-wife tried to date their Secret Service agents”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. Brittany says:

    Yeah I remember the Secret Service agents under Obama busted for hiring prostitutes on a work trip. Not so professional.

  2. Lexilla says:

    Interesting how People mag is able to text Trumps. Also, I see why this is focusing on the women because they had the power in this situation.

  3. Merricat says:

    I think Trump women have probably never been treated so well by the men in their lives as they have by the men paid to protect them.

    • Esmom says:

      This was my first thought when I first read about this. They don’t know what normal relationships are.

      It’s also not surprising that they wouldn’t be concerned about norms or ethics. The agents should have been, though.

    • Lila says:

      Yup, thought this too. Must have been a shock not to be treated like a piece of meat.

  4. Lightpurple says:

    Susan Ford married one of the agents assigned to her detail.

    The Vanessa story seems real and I love it. Junior is a cuckold, so fitting for a guy who caters to the Q crowd who love to hurl that insult at anyone who doesn’t agree with them.

    • Liz version 700 says:

      Professional ethics aside, I could totally understand Vanessa looking at the SS agent protecting her and thinking YES after being married to the whiny Jr Trump. But lord this story is wild. The Trumps are the trashiest family

      • Lizzie says:

        The agent wasn’t assigned to Vanessa but it’s a fine distinction. Agree with everything you said fellow Liz.

    • Golly Gee says:

      Vanessa has had an unbelievable love life. From a gang leader when she was still in high school, to an Arab prince to that idiot Trump and now we hear, a secret service agent. She should write a book.

      • Chicken Tetrazzini! says:

        Let’s give her a few more years, because I bet she can expand this list fascinatingly

      • Golly Gee says:

        Agreed! She’s still young and has lots of years ahead of her.

      • Courtney B says:

        I still love how she hit Jr with the divorce shortly before she came into money. He supposedly didn’t see it coming. 😂

  5. Willow says:

    Eh, everyone is consenting adults. As long as none of these people are foreign agents or are doing anything they could potentially be blackmailed for I don’t think it’s a security issue. Unless an agent protects the person they are dating instead of what they were assigned to do when something goes down? Hmm….

    • Merricat says:

      It is extremely unprofessional, and it introduces emotion into a job that requires a cool head.

      • (The OG) Jan90067 says:

        It also could lead to LITERALLY getting “caught with your pants down”. Not good if something goes down (oh geez… rereading, I didn’t realize the double entendre, and it stays! lolol)

    • Amy Too says:

      How do you say no to hanging out, on what the person you’re protecting thinks is a date, when your job is to literally follow them everywhere though? How do you escape an inappropriately sexual conversation when you have to stay all day until your shift is over? If your protectee has decided they just *have to* see you to talk about the “relationship” or to cry to you about how much they love you or want to be with you, and they call you up to come over, how do you say no when your job is to respond and show up when they need you? It just seems like even if it all started mutually and everyone was into it equally, there really is no way to step back or break up if one of them is no longer into it, or is into it way less than the other person (or on a different level: sexual vs emotional), or thinks things are moving too fast and wants to slow down.

      And the same thing for the woman. What if she’s embarrassed that things went a little too far one time and she would like to end things, but the agent is constantly there, saying things when they’re alone together, giving her looks out in public, trying to touch her, and it’s sort of hand waved away because being there all the time “is his job.” I guess it would probably be easier for the protectee to ask for a new agent for any reason or no reason because they are the VIP. But I wonder if it’s that easy for the secret service agent to ask to be reassigned, especially if the person they’re protecting insists that they like and are very comfortable with this particular agent and would not be as comfortable with a new agent.

      • Merricat says:

        It is no problem to reassign an agent; it is, in fact, encouraged.

      • Saucy&Sassy says:

        Amy Too, doesn’t this rise to the level of sexual harassment? Clearly the person in power with this family is the protectee. One of my pet peeves is that we don’t always acknowledge that men can be sexually harassed, too. I think under these circumstances, this should be reported immediately and the agent transferred away from the party who is getting too close. I agree that there can’t be emotion in a job that requires you to die for your protectee. When you mix emotion into the equation, mistakes can be made. And as said above, what happens if the agent wants out of the relationship? Is that even an option for them if the protectee doesn’t want it to end? Talk about a huge mess from start to finish.

  6. harla says:

    Personally I don’t think that Melania gets close to anyone, at any time or any where so no I don’t see her doing this.

    • Esmom says:

      I don’t know. We’ve seen how she looked at Justin Trudeau and at handsome young military escorts. I tend to think her eye wandered a lot. Not sure how far she ever took it, though.

    • Lizzie Bathory says:

      I also doubt Melania tried this. I agree that she doesn’t seem close to much of anyone, but she is rumored to be in a long-term relationship with a guy named Hank, a former (?) security guard at the Tiffany’s store in Trump Tower.

    • Jaded says:

      Well apparently she’s been boffing Henry “Hank” Siemers, the head of security at Tiffany’s in Trump Tower New York. It’s been alluded to that Trump knew about Siemers and was totally okay with it. This might explain why Melania didn’t bat an eyelash over those “grab her by the p***y” remarks during the 2016 election.

      • Merricat says:

        Trump is impotent; that’s one of the reasons he’s so aggressive about women.

  7. Wiglet Watcher says:

    With this, how they agents trashed the Obama bathroom. How the SSAgents were some of the poorest trained and Donald selected them from their private beliefs.

    There has always been issues here and there no matter the administration, but this family is trash and they bring out the worst.

  8. EMc says:

    People fall in love with coworkers all the time, so…? I’m not outraged, I guess. Obviously if it gets to the point where someone’s safety is compromised then something needs done, and it sounds like it was. I agree that it feels like the women are being belittled somehow with this article, and I don’t like it.

    • Lexilla says:

      But they weren’t coworkers. I’m not outraged either, but there are definitely power dynamics that could play into this, if the Trumps had a say in the agents’ placement or job security. (I honestly don’t know if they did?)

    • Lizzie says:

      Trade female agents and trump men and it might look like they were taken advantage of.

    • Izzy says:

      Most people’s co-workers don’t have a job description that actually includes “potentially taking a bullet for you.” This is a different kind of work environment and comparing this to a basic office romance is a false equivalence.

      • EMc says:

        Okay, ill give you false equivalency on them being coworkers. But my point remains. People that spend lengthy amounts of time together on a daily basis run the risk of developing feelings for each other. And everyone assumes it wasn’t two-sided, which is a huge factor in the situation. The power dynamics are all over the board in many relationships in regards to work. I’m gonna leave my pitchfork alone until I know more.

  9. Noki says:

    Tiffanys current fiance seems like he was forced into the situation.

    • Hell Nah! says:

      Ha ha, Noki, I love your theory!

      If nothing else, the timing of the engagement announcement made me wonder if it was fast-tracked in order to give poor, ignored Tiff some gleam while her worthless father was still in office.

      At any rate, time will tell about the fiance’s “committment” to TT.

  10. ElleE says:

    Trumps, male and female, only have one kind of relationship: manipulative (poorly stated, I know) , of course.

    The secret service needs to get out from DHS and go back to being part of the Treasury. Morale is low, professionalism is, well, you be the judge. I will say that even though the official word is that a Capitol police officer shot the terrorist breaking into the speakers chamber on Jan. 6, the man was wearing a suit and cuff links and black gloves (so prob. Pence’s ss detail actually doing his job like a professional and not getting accolades. See “low morale “ point above ssshhhhhhh)

    • Courtney B says:

      There are some capitol police, I think, who wear suits. Maybe a separate security division? I think they were some of those seen in the Chamber. But otherwise, yeah, I’ve thought it was likely a secret service agent.

  11. nicegirl says:

    Thank you so much for this post.

  12. Veronica S. says:

    I mean, not as surprising as it sounds I guess. You figure they spend a lot of time together, and unless you’re a jerk who treats them like wallpaper, you probably get to talking pretty frequently. I don’t think it’s much of a problem as long as they’re transparent about it and get replaced.

  13. TheOriginalMia says:

    I laughed when I heard about Vanessa and her SSA. Junior is so coked out these days it isn’t a stretch to believe Vanessa found comfort in a decent guy. One who probably isn’t suffering from coke-induced erectile deficiency. As for Tiff, I could see it as well. These are humans. They are going to make mistakes. Thing is that the whole agency got reviewed in the month leading up to the inauguration and the SS was found lacking. Their bias for the Trumpian way caused some of them to overlook and approve them they shouldn’t have. Hence, Biden’s old team being assigned to him & his family. Trump ruins everything and he ruined a few SSA careers.

  14. Julia K says:

    Melania is a professional trophy wife and knows she could lose out on that post nup payout. She would never get involved with her security detail. Too many loose lips in that dept.

  15. NewKay_ says:

    Is talll dark a d handsome- code for Black

  16. L4frimaire says:

    This is probably more common than you think. There were rumors Eleanor Mondale, late VP Walter Mondale’s daughter, dated Secret Service agents. A bunch of Secret Service agents were put on leave or recalled during one of then-Secretary of State Hillary Clinton’s trip to South America because they hired prostitutes. Some agents were taken off Biden’s detail because they were too loyal to Trump. The wife in an unhappy marriage and the forgotten daughter looking for attention. Sounds very cliche and nothing in the Trump WH would surprise me. An organization as large as the Secret Service is going to have scandals and org failures. This is small potatoes compared the amount of corruption and grift in that administration that has seemingly been forgotten, and shouldn’t be.

  17. Dude says:

    Carl hiasson’s latest book is about exactly this. It is a great read!

  18. Susan says:

    My dad was in the SS and for a short while, protected then prez Reagan. I remember at the time there were LOTS of stories about the Carter fam, he said Reagan was pretty chill and pleasant. The trouble w that job is it’s very “elite” so to speak but the pay is not reflective. In the 1980s my dad was making I think around 50k? Not bad clearly but not reflective of the training and expectations. We wouldn’t see him for weeks. I wonder if that is like working for the BRF in England, you do it for the “honor,” not the $$. My dad made up for it later in life with government connections, though, now that I think about it.

    • Vernie says:

      Can you elaborate on the stories about the Carters? They seem so low key and down to earth. Wasn’t it a big departure from protocol when President Carter made his staff drive themselves around, instead of all getting drivers, in order to save public funds or something?

      • Susan says:

        You know, Vernie, it’s funny, I wish I knew! My dad is now deceased and my mom is in assisted living and doesn’t remember a lot. I remember them talking about Rosalyn a lot…my dad was a die hard Democrat and was very resentful about protecting Reagan (LOL) and I know he voted for Carter so it wasn’t a political thing. I think Rosalyn gave the SS guys fits if I recall correctly. I will ask my mom next time I see her. Oddly enough, I also vaguely recall Reagan furloughing govt employees and my dad was LIVID.

    • Vernie says:

      Susan, thank you for your response! I find this DC-adjacent gossip fascinating. I lived in DC during the late aughts and had friends who worked in government/at the WH, etc. but I was a nobody with zero connections so I have to live vicariously through others, haha. Sending best wishes to you and your mom.

  19. J ferber says:

    Merricat, yes. Especially for Vanessa, who never had a real man in a marital and sexual relationship. She just had to bite the bullet, pop out kids and then dump him when her daddy made a fortune and left it to her. Of course, her choice. Personally, I’d only have done that if I were starving in Appalachia (yes, I know people starve elsewhere in the U.S.) or if I were a heroin junkie enslaved to a vicious pimp. So yes to a hot bodyguard for a delicious fling on the down low. Not so down low now, I guess.

  20. NotSoSocialButterfly says:

    Melanoma is holding out for Trudeau.

  21. Shannon says:

    Meh…this has happened a lot. The U.S. SS has done a great job of concealing all the affairs and underage relationships. Small potatoes.

  22. Holly hobby says:

    I say Vanessa deserved that SS agent after all those years with Jr. Tiffany, on the other hand is a Rump so I don’t doubt that agent wanted to be reassigned either.

  23. VoluptuousTeapot says:

    Ellee, yes. They still function as part of treasury anyway.