Here's How Much Donald Trump Jr. Really Paid For His Ex-Wife's Engagement Ring

The Republican party touts conservative family values, but it's well-known that Donald Trump Jr. — a high-profile member of Donald Trump's 2016 presidential campaign — had an affair back in 2011. The affair came to light because Don Jr.'s mistress, former Danity Kane singer Aubrey O'Day, discussed it on MTV's "Ex on the Beach" (via People). "We both thought we were each other's soulmates," O'Day told the publication in 2019. "It's something we spoke about often. A soulmate is someone you spend a period of time ... with that you're connected as one. I had that with Don." When asked why she had decided to come forward, O'Day replied that she wanted to clear the air and address the rumors of her dalliance with Don Jr.

As for Don Jr.'s wife at the time, the Daily Mail reported that Vanessa Trump discovered her ex-husband's infidelity from "sexy texts" on his phone. That's when Vanessa "went crazy and was super jealous," according to an Us Weekly source, who added that Vanessa confronted O'Day over the phone. But despite Vanessa's best attempts to save her marriage, she and Don Jr. ultimately divorced in 2018. "We have decided to go our separate ways," the estranged couple said in a statement.

As of this publication, Don Jr. has moved on with fiancée Kimberly Guilfoyle. Since news of the engagement broke, Guilfoyle has sported some serious bling on that finger, which is a far cry from the engagement ring Don Jr. once gave Vanessa.

Donald Trump Jr. certainly had the cash to purchase the sparkler of Vanessa Trump's dreams, but in the end, he opted to save his money. The New York Post branded Donald Trump's eldest "the cheapest gazillionaire" when he proposed in the Bailey, Banks and Biddle jewelry store of Shore Hills, New Jersey with a $100,000 ring. Yes, the "4-carat, emerald-cut diamond ring" had a hefty price tag attached to it, but Junior snagged the sparkler for free in exchange for allowing paps to capture the moment. It was a move that even his father "reportedly thought was a little déclassé," according to Vanity Fair.

Junior's penny-pinching ways were apparently a constant throughout his marriage to Vanessa. In 2018, multiple sources told Page Six that Vanessa's ex "treat[ed] her like a second-class citizen" and restricted her to such a tight budget that she needed to rely on others for money. According to one source, "[Junior] gives [Vanessa] very little help and has been keeping her on a tight budget. She doesn't live a lavish life and can very rarely pick up a check at dinner." Sources additionally confirmed that Junior's reluctance to share money contributed to the pair's marital woes. Another insider told People that the split had been pending for a while, and that finances were only a small part of the couple's issues. "Even before all this Trump presidency stuff started, they weren't good and their marriage was strained," they said.

Donald Trump Jr. no longer appears to be a cheapskate now that he's with former Fox News host, Kimberly Guilfoyle. The two went public with their relationship the same year that Junior announced his divorce from Vanessa Trump, per Elle. Interestingly, Vanessa leapt to her ex's defense when the media criticized him for moving on so quickly. But one thing she probably wasn't thrilled about? The fact that Junior spared no expense when it came time to propose to Guilfoyle.

Speaking to The List, diamond expert Olivia Landau estimated Guilfoyle's ring could have cost as much as $250,000. "It looks like an emerald cut, perhaps around 5 carats. It looks like there may be trapezoid side stones. This is a very classic design," Landau said. Clearly, Guilfoyle seems to have done well in her relationship with Don Jr. Unlike Vanessa, who was restricted in her funds, Guilfoyle was paid $60,000 to introduce her fiancé at a rally event in January 2021, CNN reported. This was met with widespread criticism. "We think the majority of the public would be concerned if the girlfriend of Donald Trump Jr. made $60,000 for a few-minutes speech," Mississippi Democrat Bennie Thompson said.