We all know how many people love and hate Donald Trump. His political career has truly changed how people think of him. When it comes to his son, Don Jr., personally, I think most people just DO NOT like this guy. He comes across as arrogant and smarmy. He looks like he should have been cast in the movie Wall Street or the movie Boiler Room.
Don Jr. has been in the news lately…. alot. There was a smattering of talk about him when there was all the news about Tiger Woods and Vanessa Trump’s relationship in the wake of Tiger’s traffic / DUI stop. Don Jr. Vanessa, and Don Jr. were married for just over 12 years from 2005 till 2018. They have five children together.
Is He Really Going to do The Apprentice?
After those little blurbs, there was the reporting that Amazon Studios bought “The Apprentice” franchise that Daddy Donald made so popular. And guess who they are thinking about rebooting the show with as host? That’s right, Don Jr.
Daddy Trump leveraged decades of media coverage as a New York mogul amid the ups and downs of the 1980s and 1990s into a smash-hit program that premiered in 2004, following several wannabe business executives through a several-week “job interview” to work for the Trump Organization.
Fifteen seasons and a presidency-compelled hiatus later, Amazon is reportedly considering Don Jr. for the role. As the eldest son, he has served as a frequent stand-in “boardroom adviser” for Trump executives Carolyn Kepcher and George Ross.
“He’s a good guy.” “He probably would be good.” “He’s got a little charisma going. You need a little charisma for that sucker. So, we’ll see what happens,” Trump said.
Several people familiar with the discussions told The Wall Street Journal that Amazon executives have discussed casting Trump Jr. as a host for an “Apprentice” reboot if the project launches.
An Amazon spokesperson told the Journal that the Bezos-led company previously acquired MGM, which itself bought a majority stake in reality-show impresario Mark Burnett’s company several years earlier.
Burnett has launched several reality shows, including “The Apprentice” and CBS-aired contests “The Amazing Race” and “Survivor,” with the latter now in its 50th season. The credits for “The Apprentice” list Trump Sr. as executive producer.
A reboot would be Amazon’s second foray into Trumpworld in recent months, as it recently debuted a $40 million biopic of first lady Melania Trump that drew praise from supporters and mockery from critics.
Did Don Jr. Get Married Again?
Why, yes, he did. He married socialite and entrepreneur Bettina Anderson. Their engagement was announced in December 2025. And the wedding took place in May 2026 in Florida. Now here is where it gets really strange.
Bettina’s father (who passed away in 2013) was Harry Loy Anderson Jr., who was a prominent banker and who became the youngest bank president in the U.S. In the 1990s. His bank held accounts for Jeffrey Epstein, and in 1998, he wrote a character reference letter for Jeffy to the U.S. Virgin Islands to support tax breaks. Bettina’s marriage to Donald Trump Jr. brought her further public attention, though no evidence ties her or her father to criminal conduct.
In addition to his marriage to Vanessa Trump from 2005 to 2019, he also got engaged to Kimberly Guilfoyle in late 2020, but they never married.
So that’s a lot of Don Jr. for you to handle. Have you gotten your fill yet of him?
Well, here is one other strange tidbit. President Trump did not attend Donald Trump Jr.’s wedding to Bettina Anderson, as he explained that he had to stay in Washington, D.C., for government business. Specifically, he cited ongoing international issues, mentioning Iran, and said it was a critical period for national security. The wedding was a small, private affair in the Bahamas, and while he prioritized his official duties, some people speculated about other possible reasons.
While security seemed to be the most obvious reason, there is growing thought that his health may have played a factor in the decision.
