On a chilly October day in October, 1983, I stood on the starting line of a race in downtown Oak Park, Illinois. It was fifty degrees outside. Rain had fallen the night before and the clouds still formed a low, gray ceiling above the city.

A few weeks before, I’d finished first in a 10K race called Run For the Money. It was sponsored by a bank of some sort. There was no cash prize. I considered that false advertising. After the race, one of the local runners that I’d beaten in the race introduced himself to me and explained that my finishing time of 31:42 was actually misleading. “The course is 200 meters long,” he explained. “We measured it ourselves.”
So that was more false advertising. Perhaps I’d just run a 31:10 10K? Or faster? One never knows in such circumstances.
A few weeks later at the starting line of the Frank Lloyd Wright 10K in Oak Park, my confidence was high and I was eager to run. The gun went off and once again, I led from start to finish and completed the race in 32:00, just twenty seconds behind the course record set by a guy named Tom Mountain.
I’d win the same event a year later after a year of competition in which I ran 24 races, setting personal records at every distance ranging from 5k (14:45) to 25K (1:24). My 10K PR finally did drop to 31:10, but I placed second in that race anyway.

That’s how tough it was to win back in those days. That’s why winning actually meant something. You had to earn it through hard training, race-day concentration and mental toughness.
That’s also why I’ve always held high standards about what it means to win. Because along the way to many wins, there’s also a fair share of so-called “losing” to do. If we’re smart, we learn from that.
Just as importantly, if you happen to win and then turn around and malign everyone else as losers, does that make you the ultimate winner? No, that makes you a miserable jerk.
If you also happen to be so fatally insecure that you feel like you’re winning only when criticizing or bullying others, that makes you an absolute asshole. And we all know who we’re talking about by now. Isn’t that indicative that there’s a problem afoot? That what some people call “so much winning” isn’t actually winning at all?
There’s also a pathological problem among people who feel like cheering on that type of “winning” makes them a winner too. Those are the actually the worst kind of losers in this world: the vicarious and vicious.
So in order to draw some clean lines around what it means to win, perhaps it helps to share a pair of cogent definitions of the word WIN. Perhaps that can help people understand what the word really means.
To win means: to reach by expenditure of effort.
To win means: to make friendly or favorable to oneself or to one’s cause
So let us be clear: claiming a vicarious victory by supporting a person (or a team, or a party) that behaves like a total asshole and treats everyone like “losers” does not deserve support, much less respect.
For example, it is not “winning” as a supposed Commander In Chief to show derision toward military veterans, Gold Star familiies and prisoners of war, brand service men and women “losers” and “suckers,” and call generals and heads of our military forces “dopes and babies.”
He also insults and harasses women, supports racist tropes and groups and conspiracy theorists, as well as lies and downplayed the threat of a dangerous and deadly pandemic. He does it all because the only thing he claims to care about is “winning.”
In Trumpian terms, that is short for “he only cares about himself.”
That is the hallmark of a sociopathic loser. His supporters own that moniker as well. Everyone who supports Trump is behaving like the losers and suckers that he assumes that they are. It’s so simple to see. And so hard to avoid.