I confess; I once wrote a fan letter to Donald Trump. It was 1987-88. I had a First Edition copy of The Art of the Deal, and was just starting back to college after being out of school for four years. I was a Finance major at the University of Massachusetts in Boston. I subscribed to Money and Fortune magazines. Donald Trump fascinated me. Even at the time, he was famous primarily for being an egotistical blowhard with little skill, business or otherwise, but a great deal of chutzpah—enough to make him an interesting character and to make himself a lot of money. I regarded him as a modern day P. T. Barnum.
In The Art of the Deal, Trump wrote about his plans to develop a large spot of land on the west side of Manhattan, the site of a former New York Central Railroad yard, into something called Television City. It was typical Trump: an audacious idea with an equally outrageous name. In my fan latter, I told Mr. Trump that I hoped to be one of the development’s first residents. Television City never happened. The project eventually morphed into Riverside South on a much smaller scale than the original plan, and was sold to various investors including some from Hong Kong and China. I do not live there.
I followed Trump for years, buying his other books as they came out, and reading about him in financial magazines and newspapers. I enjoyed watching him in interviews. He was larger than life, the embodiment of so many of the traits Americans highly prize even if we don’t want to admit it: abundant self-confidence, an unapologetic hunger for money and power, and an overwhelming sense of American exceptionalism. The late 1980s was the era of Tom Wolfe’s Bonfire of the Vanities, Oliver Stone’s movie Wall Street, and the hero worship of financial wizards like Michael Milken, Ivan Boesky, and Peter Lynch. Okay, so some of them landed in jail, but the main thing was they made a lot of money!
When Trump threw out the idea of running for president in 2000, I initially thought he would be a strong contender. His stated views at the time were relatively moderate. Then when he made another short trial run in 2012, an online “Which candidate do I agree with most” survey told me Trump should be one of my top picks. Again, he seemed reasonably moderate…for a while.
Then he stated on the birther thing, insisting that Obama was not a natural born citizen. I started having second thoughts about Trump. By the campaign leading up to 2016, Trump had clearly decided to court the extreme right, including white supremacists. He ran a shock campaign, employing all the spotlight grabbing tricks he had learned over the years. His successful “reality TV” career had taught him that outlandish behavior and inflammatory pronouncements garnered impressive viewership ratings. The Donald Trump who had amused and entertained me was gone, and in place of that over-the-top but still likable character there was this repulsive bully spouting hatred and playing to the lowest common denominator.
I hoped the other Donald Trump was still in there somewhere, and that this new guy was just playing a game to get attention. I was wrong. His Republican rivals underestimated him, but the Democrats made a much bigger mistake. They assumed that since Trump had basically been laughed out of the election process early in the game in both 2000 and 2012 he was easily beatable. They were horribly wrong.
The letters I have been sending my Senators (Grassley and Ernst) and the White House lately have not been fan letters.