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He even has controlling interests in many MSM outlets from what Some claim, he owned 56% of the media at one time but has since dropped his interest to around 27%.

Sorry, but that's ridiculous. Who ever said that doesn't know what they are talking about.

Let's review, shall we.

There are the so called "Big Six" media conglomerates. They are: GE, Disney, News Corp, Time Warner, Viacom, and CBS. Here is a handy link where you can review what these corporations own: The Big Six.

Now lest look at what it would mean to own 25% of these, based on their current market cap.

GE's market cap is $209B. So call that $50B.
Disney's MC is $80B, Trumps share $20B.
News Corp. $40B, Trump's share $10B,
Time Warner MC $38B, Trump's share $9B,
Viacom MC $27B, Trump's share $7B
and finally CBS $16B, Trump's share $4B.

50+20+10+9+7+4 = $90 Billion.

Forbes most recent ranking of Trump's net worth was $2 billion. So, there is no way he owns "27% of the MSM" or anything close to it. Also, most of his net worth is tied up in property, the source of his wealth.

I seriously doubt he has a significant position in ANY media company.

Cheers!