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Winners & Losers | King Loser and a (Hopeful) Glimpse into the Future

This can be the year that we stop reeling from the punch and start fighting back.

Sam Osterhout's avatar
Sam Osterhout
Jan 05, 2026
∙ Paid

Let’s consider the turning of the year a blank slate. Forget about all the Losers and all the Winners from last year (don’t worry, you’ll have plenty of opportunities to think about them again … very soon, I’m sure).

Over the next year, if my math holds out, we’ll have an opportunity for 52 new Winners and 52 new Losers. There are bound to be repeats. Plus, if we run our end-of-year Tournament of Champions, there will be a few less of each to ponder.

Nonetheless, the whole point of this column is to keep track. We are pinpointing the people who are behind the problems we’re facing — the Losers — as well as those who are standing in their way — our Winners.

Remember: all the chaos we see is caused by people. And people will be the solution, too. We need to name them.

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Loser #1: Donald Trump

I was going to pick him this week, even before his adventure in Venezuela, just to set the table for the year ahead. But geez. We haven’t even rounded the first week of 2026 and Trump has invaded Venezuela and kidnapped its leader, threatened Iran with violence if they mistreat peaceful protestors (because we all know how dearly he holds the right to protest), and put Cuba on alert (it was Marco Rubio who put voice to that threat, to be fair).

If anyone was wondering if Trump would continue to be Trump in the new year, wonder no more.

Some have argued that Trump — our King Loser #1 — is a symptom of our disease, and not the cause. I’ve been skeptical of that assessment in the past, but now I see my doubts were the result of my emotional need to blame someone.

Someone needs to be responsible for what’s happening here, right? If we can just name the people doing all this crazy stuff, we can hold them to account, and everything will get better.

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