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​Donald Trump's latest sparring partner: a Saudi prince

The New York Times has compiled a list of everyone GOP candidate Donald Trump has insulted since he started his presidential campaign
Who has Donald Trump targeted the most? 01:09

Move over, Megyn Kelly. Republican presidential candidate Donald Trump has a new target for his ire.

The latest to feel Trump's lash is Prince Alwaleed bin Talal, a Saudi prince and investor who is worth $19.2 billion, according to the Bloomberg Billionaires index. Interestingly, Alwaleed's relationship with Trump wasn't always so adversarial, given that the prince bought assets from Trump in the 1990s when the real estate mogul's finances were on shakier footing.

Alwaleed's investment company, Kingdom Holding, owns stakes in Lyft and Twitter, the latter of which is, ironically, where much of the spat with Trump is playing out.

Alwaleed may not be a household name, but he's long captured the attention of American investors, both for his savvy money decisions and his flamboyant lifestyle. Among other high-profile financial moves, Alwaleed invested $590 million in Citibank in 1991 after the bank had suffered some financial setbacks, and took a stake in Apple (AAPL) in 1997. More recently, in 2013 he bought a $300 million stake in social media firm Twitter (TWTR).

Both investments have reaped rich rewards for the prince. As for his lifestyle, his 460,000-square-foot complex in Riyadh has a staff of 100 and 371 rooms, according to Vanity Fair. He's also been reported to engage in hobbies such as falconry.

While Alwaleed's extravagance might seem right up Trump's alley, a spat has been simmering since late last year, when Trump called for the U.S. to ban all Muslims from entering the U.S. At the time, Alwaleed tweeted that Trump should give up his aspirations to earn the nation's highest office and called him a "disgrace." Trump, for his part, called the prince "dopey."

Megyn Kelly: Donald Trump tried to "woo" me 02:07

The latest twist came on Thursday when Trump merged three of his pet peeves -- Fox News, host Megyn Kelly and Alwaleed -- in a tweet that seemed geared toward undermining Fox News by suggesting foreign ownership. (Trump boycotted Fox News during Thursday night's GOP debate.) Trump's tweet included an image of Megyn Kelly flanked by Alwaleed, along with the text, "Most people don't know that the co-owner of Fox News is Prince Alwaleed of Saudi Arabia here with his sister and with host Mygan [sic] Kelly."

There are a couple major problems with the Trump's tweet, however. First, it's photoshopped, with one Twitter user pointing out to Trump that "it looks like it was made by a 3-year-old in MS Paint." The photo also isn't exactly new, given that it was debunked by urban legend site last year.

Second, it's not true that Alwaleed is the co-owner of Fox News. The prince first invested in News Corp. in 1997. In 2013, News Corp. split into two companies: 20th Century Fox, which includes Fox News, and the "new" News Corp. While Alwaleed continues to hold a significant portion of 20th Century Fox's shares, he's hardly a co-owner, given that implies controlling half of the company. Alwaweed's stake in the media business is about 7 percent, according to a recent regulatory filing.

What most people actually don't realize is the connection between Alwaleed and Trump goes back decades, mostly with Trump benefiting from Alwaleed's deep pockets.

In 1991, Alwaleed bought Trump's 283-food yacht from creditors at what BusinessWeek called "the knockdown price of $18 million." Four years later, Alwaleed and his partner acquired majority control of The Plaza, the luxurious New York City hotel, buying out Trump and opening the door to creditors forgiving Trump $125 million in debt.

Those long-standing connections weren't lost on Alwaleed, who had a zinger ready to fly after Trump tweeted the photoshopped image of himself and Megyn Kelly.

The prince shot back, "Trump: You base your statements on photoshopped pics? I bailed you out twice; a 3rd time, maybe?"

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