10 Scandals Surrounding Kate Middleton's Brother, James

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"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.

Kate was not pleased as at this point she had been waiting more than seven years to marry her prince. In the end, James was not implicated in any wrongdoing. But still, this was the sort of scandal that could have cast a huge dark spot on not only the pending Royal Wedding, but the entire Middleton family.

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.

And this was only 90 minutes after they had arrived! Kate was visibly embarrassed and tried to hide her face. She made no effort to help her brother, while their mother Carole Middleton tried to (unsuccessfully) stop all the people taking pictures. She was obviously unsuccessful. She even chased down one photographer who was capturing the moment her son urinated on a fence! It sounds like quite the debacle. And quite the family outing!

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.

When he baked the 21 cakes, one was made with the image of the beloved Diana, the late Princess of Wales, on it. The gesture was seen as "insensitive" and he was accused of profiting from his royal connections (at this point in time his sister was two years away from marrying the future King of England). I really don't see the issue paying homage to the beloved Princess Diana. But at this point, he was already seen as a potential liability to Kate, and this only worsened that sentiment.

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.

While there, he bought some items for his sisters (not sure I would want my brother picking out my clothes- weird). They have been called an "odd couple," "unlikely friends," and have even rumored to be more at times.

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!

Though these unflattering photos became famous the week of the Royal Wedding (no coincidence there, I'm sure), some date back as far as 2008, meaning they were taken during James' college years. What did you expect? He got kicked out of hosh posh club, certainly he's done worst in college! So it is not as shocking, then, that they were taken at all. Boys will be boys, will they not?

5. Is He Gay...

There are many people who suspect James Middleton of being gay, and I can't say that I blame them. Some of his choices are indeed questionable. First, his plus-one to William and Kate's Royal Wedding was his male best friend, a fact that was deliberately kept quiet precisely because of the rumors about his sexuality. He is often referred to as "flamboyant" in the press, and he has many close friendships with men. For a while he had a noticeable lack of girlfriends in his life (platonic or romantic), which of course only fueled the rumors of his homosexuality. There really is nothing wrong if he was. Sure, it'd be treated as a bombshell if he did come out. But in this day age...who cares, really?

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.

He is said to have a thing for foreign women, and thinks that the gay rumors are funny. It seems as if perhaps Donna was the one to settle him down though, as he dated her for three years and even played daddy to her daughter.

3. Bailed Out By Mommy And Daddy

James was forced to turn to his parents for financial support after his cake business suffered huge losses in 2012. He allegedly owed creditors $50,000.00. Luckily for everyone involved, Michael and Carole Middleton were able to help, as their own business Party Pieces has made them millions over the years. The business basically owes creditors more than it was earning, which apparently is not uncommon for start-up businesses, especially in the economic climate of 2012. James had this to say of the situation: "I made the decision to finance the business myself along with a loan rather than go to investors. This has its pros and cons. It does mean things don't move as quickly as I would like but it does mean I keep complete ownership and control over my company." Hey, he sounds like he has a good head on his shoulders.

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.

But it is just so random that it comes off as somewhat shocking given that coming out to one's family is generally quite a serious discussion to have. Terrifying even. But nevertheless, James says of his Boomf marketing ploy that his "sweets are the perfect way to break the news to family and friends." This is madness all around, folks. First of all, the marshmallows. Just... huh? Second of all, in this day and age when everything offends everyone, it is sheer madness to publicly even hint at using marshmallows to come out as gay. But alas, he did.

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: metro.co.uk; dailymail