10 Scandals Surrounding Kate Middleton's Brother, James

"Lumberjack," "Wildcard," "Black Sheep"- there are many things that James Middleton has been called in his day, and especially since his big sister Kate became famous when she and the future King of England began courting all the way back in 2002. But this man is most famous for being Kate's little brother, to his dismay, as he claims he wants to be known for his business. It is true that this entrepreneur has found some success with his very-random marshmallow business (yeah, more explanation later), but it has not come without cost, both financial and otherwise.

James' business ventures are just one small element of his life, which over the years has included nude photo scandals, drunken debauchery, rumors in the media and around the world of his sexuality, and more. This of course is very displeasing to the Royal Family, and embarrassing for his sister, the future Queen of England, who is almost always seen looking only prim, proper, perfect, and ready for a tea party.

But not James! He falls more in line with their other sister, Pippa, who has also dabbled in scandals from time to time. Between the two of them, they must give poor Kate more gray hairs than her two little ones (and speed up the process of Prince William's thinning hair too)!

For now, we will focus on the family's only son, James William Middleton. The following 10 inappropriate instances in James' life  are shocking but amusing, and have undoubtedly shamed his royal in-laws time and again. Cheerio!

10 Get-Rich-Quick


Before the world famous 2011 Royal Wedding of Prince William and Kate Middleton, her troublemaker little brother was involved in an "embarrassing" scheme. He worked for a get-rich-quick investment firm that was under investigation for alleged financial funny business. Basically, the company was accused of selling investments in a rainforest that did not yet exist. It was rumored that the much-anticipated Royal Wedding was even pushed back because of the scandal to make sure it didn't "taint" the marriage or disrupt any wedding festivities.

9 Drunken Spectacle


Everyone likes to have a drink here and there, especially to celebrate one's birthday. During a celebration of his 22nd birthday in 2009, James got so drunk he was practically carried by his father Michael Middleton and sister Pippa Middleton from a members-only London nightclub that is a hot spot for young royals. Wow, talk about an awkward walk of shame outside such a club.

8 Insensitive Baking


As we know, James Middleton is a lover of the baked good. In 2009, the cake-making entrepreneur's talents backfired while he was attempting to do something good. He had received an offer from the magazine Hello! to make 21 cakes to celebrate their 21st birthday. Kind of a waste of cakes, if you ask me.

7 Mischa Barton


In 2012, Mischa Barton of The O.C. fame threw a party in London to celebrate the opening of her first-ever clothing store, Mischa's Place. James Middleton was a guest at said party, and the two were rumored to have a "friendship". He apparently did the cupcakes (200 of them!) for the fashion bash, but since he attended with his then-girlfriend Alejandra Welsh Pena, rumors of anything beyond a friendship were short-lived. Talk about an unlikely friendship.

6 Photo Scandal


And it was just in time for the Royal Wedding! Somehow, photos were leaked of the soon-to-be princess' foolish younger brother doing all sorts of crazy things.  Some of his less-than-classy poses include his hands down his boxers, lounging completely naked with his hand in his crotch, exposing his butt, mimicking sex acts with friends (men), and dressed in a French maid's costume.  I don't know where to begin. First, what goes in someone's head to spark such tasteless actions? No one wants to see such photos!

5 Is He Gay...


4 ...Or A Ladies' Man?


Contrary to suspecting he is gay, he is also rumored to be a ladies man. People and their gossip, I swear! And apparently, these people also cannot make up their minds. Anyway, this contradictory rumor is because (according to some) he actually has had a long string of girlfriends but has chosen, perhaps wisely, to keep them to himself. They include a Brazilian model called Fernanda, Australian Amy Bradshaw, his friend's sister Francesca del Balzo, and eventually his longtime girlfriend, Donna Air.

3 Bailed Out By Mommy And Daddy


2 Marshmallow Madness


James came under some scrutiny when he suggested that his customers (and everyone) used his business (aka personalized marshmallows- how does one even come up with that idea?) to come out as gay, essentially using marshmallows as a tool to reveal to your loved ones the one thing you are likely more afraid to tell them than anything else in your life. In one way, I can see that something so frivolous and light-hearted such as marshmallows could deter from the serious nature of the conversation.

1 His "Relationship Sabbatical"


Umm... is that a thing? Apparently, at least for Royals (or their relatives) it is. Back in the days of lovable Friends faves Ross and Rachel, it was just called "taking a break." But now you can have a full-on sabbatical. Sweet! For James Middleton and longtime love Donna Air, they recently faced his move to Hong Kong to promote Boomf, and that is an understandable strain on any relationship. Donna has to stay in London with her daughter Freya. Various sources have said things like that this could be the end of the road for them, that they will "stay in touch as often as possible", and of course, there is that silly but intriguing concept of the "relationship sabbatical", a phrase quoted by a source close to the couple.

But not to worry; during this 6,000-mile separation, James has made sure his cocker spaniel Ella has a passport to go with him to the southeast Asian country. And if that is not enough to combat his loneliness, we all know that China (or the city China likes to think of as "theirs") has plenty of willing women in those massage parlors on every street corner. We wish you luck, James and Donna! Oh, wait... yeah, they broke up in February.

Sources:; dailymail

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10 Scandals Surrounding Kate Middleton's Brother, James