Get ready, the “Stalker-in-Chief” is coming for us.

In the 1991 film, Sleeping with the Enemy, Julia Roberts goes to extraordinary lengths — even faking her own death — to escape her abusive husband. The film is part of an entire genre of movies in which the unsuspecting are initially attracted to charismatic people, only to discover the object of their affection is a psychopath.

In fact, the stalker plot is a go-to format in film and television. I’m amazed at how much of the Netflix library follows this formula: Sexy person / couple / college student / lawyer / new employee meets sexy co-worker / client /…


During the last Presidential campaign, one of Donald Trump’s main selling points was that he was an uber-successful billionaire, and he would bring that unique business skillset to the White House to catapult America into the stratosphere.

But recently, newly released Trump tax data showed he actually lost $1.7 billion dollars, more than any other taxpayer, over a nine year period. The President is very concerned that no additional details of his finances are released to the public, filing lawsuits to resist all investigations into his taxes.

I have no idea whether or not Trump is a billionaire or a…


I lost a friend to lung cancer a few years ago, which unfortunately did not come as much of a surprise. He was a thoroughly addicted smoker — the kind of guy who lit a cigarette with a cigarette. Friends and family did everything they could to get him to quit, warning his addiction could only lead to serious disease and death. But he’d have nothing to do with those kind of reasonable predictions.

“Hell, I’ll probably die in a car wreck before these things get me,” he said in a raspy smoker’s voice. Even when he received his diagnosis…


You can’t win the game if you don’t know the objective.

Winning has always been an important component of the American identity. It’s incomprehensible to most Americans not to be the best: the most powerful, the smartest, the most admired, the most feared. This was an important selling point in the Trump campaign, as he made the compelling promise, “We will have so much winning if I get elected that you may get bored with winning.”

Many are ready for the winning to commence, but the big problem with a statement like that surrounds the definition of winning. In this…


Let’s take a hard look at how he’s managed his brand in the past…

I recently asked a salesman at Nordstrom’s if dropping the Ivanka Trump brand had impacted business. “Nope,” he smiled. “A guy just came in and dropped $700 on shirts he’d planned to buy somewhere else.” Nordstrom’s stock price is up since the President went on a tweet warpath over their decision.

On the Trump-positive end of the spectrum, Ivanka’s perfume sales increased on Amazon, and after a group organized a boycott of Trump wine, retailers sold out. But politically-motivated purchases are an unsustainable long-term brand strategy.

One of the biggest controversies we face is an issue of branding. Is the…


A year ago when Donald Trump emerged a serious political contender, I noticed how uncannily he followed the infomercial huckster bible I’d help develop two decades earlier.

When I was in my twenties, I wanted to work in television, and infomercials offered a way in. The industry was still in its infancy, and could be incredibly lucrative. A single infomercial could produce over $100 million in sales (my record generated over $360 million), so the economics were appealing.

My specialty was working with established companies that utilized the format as an additional marketing channel, with clients that included companies like…


Smacking a religious figure was a risky move, especially in a foreign country.

When I was sixteen I punched a Priest. Father Dan was a little padre, about my size at the time. A big Irish or Pollack father would have sloughed off my pitiful jab and pounded me into the sidewalk. But Dan, possessing the pliable heart of a true drama queen, fell into the gutter and began to wail.

It was London, England, 1976. In those days smacking a religious figure was a risky move, especially in a foreign country. You might be charged with some ancient statute…


My father was a collector of sorts. But most unusual — his soap collection.

My father was a collector of sorts. Not the kind of man that collected cars or coins or anything most people would perceive to be of value. Little chance we would discover dusty Pollock’s and de Kooning’s squirreled away in a basement corner — Dad unaware or unconcerned with the fortune that lived by the furnace — paintings mysteriously acquired after World War II in trade for a bottle of port or a carton of cigarettes after a drunken night of Greenwich Village revelry. Nothing that…

Timothy O'Leary

Author of Dick Cheney Shot Me In the Face: And Other Tales of Men In Pain. Plus a lot of other stuff. www.timothyolearylit.com

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