What’s the Deal with Trump and Playboy?
This week both Trump Jr and Sr were in the news for allegedly having affairs with Playboy models. But Trump has been a fan of the magazine for a lot longer than that.
It’s been recent news that Donald Trump Jr., the desperate-eyed, chinless heir to the Trump throne, had an affair with singer/reality TV personality Aubrey O’Day. They worked together on season five of Celebrity Apprentice in 2012. In 2009, O’Day posed for Playboy. She and Donald Trump Jr. reportedly had their affair in 2011. And in 2013, the first song on O’Day’s album was a torch song called DJT. (Shhh those happen to be Trump’s initials.)
What’s interesting about all this, other than the mystery of how anyone finds members of the Trump family at all attractive, is the Playboy connection. Fun fact: Out of the seven seasons of Celebrity Apprentice, there was only one season that didn’t include a contestant who had posed for Playboy.
Season 1 had two!
Carol Alt—the super swimsuit model of the 80s—posed for the magazine in 2008, when she was 48.
Tiffany Fallon was the Playmate of the Year in 2005. It’s a wonder diehard Christian Stephen Baldwin was able to participate. That season also happened to be the last time Omarosa was ever heard from again…
Season 2
The season that the late, great Joan Rivers won (another fun fact: she was one of only two female winners in the entire run of the series. Probably just a coincidence,) also starred Brande Roderick, Playboy’s Playmate of the Year for 2001.
Season 3
The Donald (and Donald Jr) would have to be satisfied with Selita Ebanks, a Victoria Secret Angel and Sports Illustrated Swimsuit model.
Season 4
Perhaps making up for the previous year, this season had three women who posed for Playboy. Though, to be fair, La Toya Jackson and Lisa Rinna (who posed for the magazine twice, once in 1998 when she was pregnant, and again in 2009) are certainly famous for other things. But Hope Dworaczyk, Playmate of the Year in 2010, not so much.
Season 5
Another banner year. In addition to Aubrey O’Day, this season starred former pop icon Debbie Gibson (who posed in March 2005) and Relic Hunter Tia Carrere (Janurary 2005). And, though she didn’t pose for the magazine, comedian Lisa Lampanelli wrote a column for Playboy for a while.
Season 6
This All-Star season saw the return of Lisa Rinna, Brande Rodericke, and La Toya Jackson. Also, Stephen Baldwin.
Season 7
This season really only had Vivica A. Fox, who was in Playboy in 2004, but it remains a mystery to what degree of undress she was.
Season 8
This season was actually hosted by Arnold Schwarzenegger, much to the chagrin of POTUS. Nevertheless, in the name of transparency—because clearly it wasn’t just the Donald demanding Playboy models—this season did include celebrities who also happened to pose for the magazine: Brooke Burke-Charvet, Carrie Keagon, and Carrie Wilson of Wilson Phillips. Right?
While a similar article could be written linking the Real Housewife franchise with Celebrity Apprentice, since there were plenty that were fired by Donald Trump, there has yet to be any rumours about either Trump dallying with one of them. Whereas Trump’s fondness for Playboy—as well as Playboy’s embarrassment over the same—is well-documented. In fact, just this week, Karen McDougal (PMOY 1998) filed suit similar to Stormy Daniels’ against Trump seeking the right to speak publicly about an alleged affair she had with the future POTUS.
The connection between the Donald and Playboy made a certain kind of sense though, at least in the 90s and early aughts. Back then, Playboy and Trump were both past their prime, making money on regrettable licensing deals, and bordering on self-parody. They both represented a kind of waning machismo and false luxury. They’ve since gone in different directions. Under the creative control of Cooper Hefner, Playboy has tried to make a return to social justice and free expression, whereas Trump has become the embodiment of all that is wrong with America. Example: Trump tried to ban transgendered people from joining the military, Playboy, under the creative control of the slightly less problematic Cooper Hefner, had their first transgender Playmate. Obviously, serving in the military and getting your picture taken topless are not comparable activities, but you get the point.
Now, to be clear, I am throwing absolutely no shade on the Celebrity Apprentice contestants, either for posing for the mag, or for starring on a sad reality show that contributed to the downfall of democracy—a woman’s got to work, and even Donald Trump himself didn’t think he’d win the presidency. But, since the Trumps seem to treat the adult entertainment industry—and Playboy in particular—as a kind of Ashley Madison catalogue, it does make us wonder if there will be more stories to come.
