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A Long Look At Losing And Lovable (And Loathsome) Losers

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As we were preparing for our show on underdogs, I kept saying that we shouldn't overlook the fact that, often, to be an underdog in the first place, you have to be relatively bad at the thing you’re an underdog about.

The more we talked about it, the more I found myself making the case that losers and losing are fascinating.

And they are. There's a whole podcast about political candidates who lost. We romanticize losers in movies and TV and songs and stories.

And think just about the phrase "lovable losers." In a culture where we focus seemingly entirely on the positive half of the zero sum, where we endlessly exalt WINNING, it's kind of interesting that we love the losers too, isn't it?

This hour, a long look at losers and losing.


  • Jason Cherkis - Political reporter for The Huffington Post and the co-host of Candidate Confessional
  • Josh Keefe - An investigative reporter at the Bangor Daily News; in a piece for Slate's Sports Nut, he claimed that he was the worst high school quarterback ever
  • Jonathan McNicol - Producer at Connecticut Public Radio
  • Irene Papoulis - Teaches writing at Trinity College
  • Brian Slattery - Arts editor for the New Haven Independent and a producer at WNHH radio

Join the conversation on Facebook and Twitter.

Colin McEnroe and Betsy Kaplan contributed to this show, which originally aired August 1, 2016.

Jonathan is a producer for ‘The Colin McEnroe Show.’ His work has been heard nationally on NPR and locally on Connecticut Public’s talk shows and news magazines. He’s as likely to host a podcast on minor league baseball as he is to cover a presidential debate almost by accident.
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