Trump: Why the Media Loves to Hate

I learned something new this weekend—and it has nothing to do with Donald Trump figuring out ways to legally game the tax code.

It’s that this story resonates well beyond its import, which means to me, the real news here is about the media’s obsessive and compulsive attempt to block the possibility of a Trump presidency.

Reporters generally hate anyone the GOP puts up, but Trump is a particularly inviting target for their left-wing animus, and it goes beyond his attacks on liberal shibboleths like immigration. It’s a jealousy-rooted hate that envelopes Trump’s whole persona; his ostentatious use of his wealth, his beautiful wives [from all three marriages], and of course, that he’s television famous.

Most reporters, particularly those on the print side of the profession, yearn for more TV time to hump their stories, books and possibly provide a little side income to supplement their crummy salaries. Trump has manipulated the tube while making news and money controlling the medium, and in some cases, the executives that run it.

Because of all that, most reporters, would rather elect a near felon than someone they loathe because his wealth, wives and orange skin, which is why not a day goes by that some news story is written much less to inform but to put another nail in the Trump presidential coffin.

Take the New York Times tax story from last weekend. Kudos to the Gray Lady for a great scoop. What blew me away were headline numbers that stated Trump took a nearly $1 billion loss on his income in 1995 – the result of business dealings gone terribly wrong in the early 1990s-- might have allowed him to write off 18 years of taxes on income.

I wouldn’t have hesitated to report this stuff if Trump’s tax returns mysteriously landed on my desk, which is basically how the paper’s two reporters got the documents, so they said on national television.

Of course I would have added some context. Who really didn’t know much of this stuff about Trump’s business and aversion to pay taxes? Trump’s near brush with bankruptcy in the early 1990s is legendary. Even before last week’s debate, Trump bragged about how he uses IRS rules to avoid paying even a dime in taxes that he doesn’t have to pay.

Then there’s the nonsensical pile on to yes, give the story some “context.” Some commentators are arguing the big loss proves Trump is a lousy businessman (a B.S. argument since businessmen lose money all the time, but indulge me for a minute), while others say his use of the system to avoid paying taxes on millions of dollars of income proves the class-warfare argument that the deck is stacked in favor of the rich and successful.

Which is it? Is the Donald a failed businessman or a really rich successful guy who uses an unfair tax code to save money? The media elite can’t seem to make up its mind.

I’m no blind defender of Trump, who I have known for much of my career and full disclosure, I like the man even if I have taken plenty of shots at his wild and sometime grotesque statements. He is clearly not the strongest GOP candidate to challenge Hillary Clinton—Marco Rubio, John Kasich and even Ted Cruz would be tying her in knots by now given the state of the Obama economy she needs to embrace to get the president’s endorsement, as well as her own near felonious behavior involving her private email server as President Obama’s secretary of state.

Trump’s blind spots are ubiquitous; aside from being involved in a line of business (real estate) that demands sharp elbows and making lots of enemies, he has no filter and has engaged in noxious debates on everything from the alleged criminal activity of illegal immigrants to the weight issues of a beauty pageant queen.

He’s also not someone who immerses himself in policy, which until now has been a prerequisite for any major-party presidential candidate. And it has cost him: His lack of policy chops showed itself to be a fatal flaw in the first debate, which he clearly lost.

On top of all his missteps on the campaign trail Trump made a real bone-head decision not to release his taxes early and deal with the fallout then and not a couple weeks before the presidential election.

But Trump is no felon because of his tax losses and write offs or presumably he would have been indicted by now. Yes, he lost a lot of money in the early 1990s, but he’s made a lot of money since by being a shrewd  businessman, not making the same mistakes he made in the past (taking outsized risks while branding and licensing his amazing name and personality).

He’s been the target of everyone in the media for many years, but he’s shown an amazing resilience and has come back more times than most business people I know.

The coalition align against Trump is an odd one; lefty reporters and conservative pundits who are engaging in a self-defeating Schadenfreude. See what Hillary Clinton wants to do vis-a-vis the economy, taxes Supreme Court judges, etc. and the choice for any real conservative isn’t even close.

Sure, Trump says some dumb things, but his tax plan is about as pro-growth as they come for business and individuals, and I can’t imagine a GOP congress will indulge his fantasy about rewriting trade pacts like NAFTA or scrapping the Trans-Pacific Partnership (TPP). Clinton, like her predecessor and most of the left-wing of the Democratic Party have been enacting some really dumb things for the past eight years and they would like to continue this roll for many more.

People in the Trump campaign tell me they’re bracing for more tax disclosures, and that means more attacks from the left (i.e. most of the main stream media) and the right (i.e. the majority of the conservative pundit class).

If he survives this onslaught and wins in November it will be his greatest comeback by far.