In 2011, Richard Wooten ran for 6th Ward alderman in Chicago. He lost.
In 2015, he ran again. He lost again.
In 2019, a third time. Lost.
In 2023 — twelve years after the first attempt — he ran one more time. Out of eleven candidates, he finished second, forced a runoff, and took nearly forty-two percent of the vote against the eventual winner, William Hall. It was, by a wide margin, his closest and strongest showing.
He still lost.
Four elections. Four losses. Twelve years between the first and the last. If you’re looking for the version of this story where the fourth loss turns into a win, this isn’t that story. This is the story of a man who kept showing up to be told no by the same neighborhood, again and again, for over a decade — and what that actually does to a person, which is not what most of us assume.
What losing in public actually teaches you
Most men never lose anything in public. That’s not a compliment to them — it’s usually just the shape of their lives. They avoid the arena. They don’t run for the thing that could say no to their face, in front of everyone who knows them, with a vote count attached to prove exactly how badly they lost.
Richard did that four times.
There’s a particular kind of training that only public failure provides, and it has nothing to do with talent or strategy. It’s the training of getting told no, clearly and repeatedly, by people you respect — and finding out what’s actually left of you once the applause and the title you were chasing don’t materialize. Most men spend their whole lives protecting themselves from ever finding that out. Richard found out four separate times, over twelve years, with his name on a ballot and his neighbors’ decision printed in the newspaper the next morning.
That’s not a small thing to survive. It’s a specific kind of strength, and it’s one most men have never had to build, because they’ve never been in a position where they had to.
The 2023 runoff
The closest he came was also the last time he tried. Second out of eleven candidates. A runoff. Nearly forty-two percent of the vote against a well-run opponent. If there was ever a moment where the story could have ended in victory, that was it — twelve years of showing up, and this time it was close.
It wasn’t close enough. And what’s worth noticing isn’t the margin. It’s that a man who had already lost three times, publicly, put himself back in front of the same neighborhood a fourth time — closer than ever, and still willing to lose again if that’s what it came to.
That’s not stubbornness for its own sake. That’s a man who had already done the hardest part of failure — surviving it, in public, more than once — and who wasn’t afraid of doing it again.
If you’re in the middle of a failure right now
Maybe it’s a business that didn’t work. A promotion you didn’t get, again. A relationship, a ministry, a plan you built carefully and watched not come together — possibly more than once. If you’re in the middle of that right now, here’s what twelve years and four elections can tell you that a motivational quote can’t: losing in public doesn’t disqualify you from anything. It trains you for something most people never get trained for — the ability to keep your footing when the room tells you no, and to decide for yourself what happens next instead of letting the loss decide it for you.
That’s not a skill you get from winning. You only get it from losing, surviving it, and choosing to show up again anyway.
Where that training goes now
Richard isn’t running for anything anymore. What he built instead, out of twelve years of public failure and everything that came before it, is the Men’s Reset — a space for men who are in exactly the position he spent over a decade in: showing up, again, after being told no, trying to figure out what’s actually left of them underneath the loss.
If you’re in the middle of a failure right now — public or private, recent or years old — you don’t have to figure out what it means about you by yourself.
Richard Wooten is a United States Army veteran, a retired Chicago Police Officer, and minister and founder of The Gathering Point.
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