Sinatra once called Chicago "That Toddlin' Town" — now I know what he meant

Last week the Chicago Tribune’s blog platform, Chicago Now, surreptitiously shut down. Whether it was a business decision or the Trib simply forgot to pay the GoDaddy bill (believe me, I’ve done this), it was disappointing to see the web community go. Chicago Now was the first place, being dead honest, where I built consistent habits as a writer.

Moreover, a long list of sports media personalities was part of it. Before joining ESPN, Sarah Spain blogged there, as did attorney-turned-sportswriter and radio ace Julie DiCaro. And another regular was our own Candace Jordan. Chicago Now was the kind of place, as I’ve described here before, where you became part of a community. But it wasn't the only place—Chicago has a lot going on in that area.

Before my first Chicago Now post in 2011, I got an invite to the 103rd annual “Next Year Day,” the yearly celebration at Casey Moran’s bar. Weeks before Opening Day, Cubs fans would celebrate two things on Next Year Day: 1) not winning a World Series the prior season, and 2) the next upcoming baseball season—and thus another chance to win a World Series.

That evening in Wrigleyville, after several beers and a Ronnie Woo-Woo sighting, I stepped outside and bumped into Sun-Times sportswriter Rick Telander. Telander was pretty dressed down, talking with another Cubs fan, and if I remember right, was having a cigar with the guy. I said hello and introduced myself as any sports enthusiast would.

There, Telander and I struck up a conversation about baseball. Between our thoughts about what might transpire in 2011—note: the Cubs would go 71-91, nothing special—he asked me what I was working on. Somehow, I let it out that I had a new sports blog under the Tribune’s banner, and Telander offered encouragement and advice about sports writing.

I remember him saying, “write what interests you and write about what you love.” Mind you, Telander didn’t know the first thing about me or whether I had any talent. But it probably came from his kindness as a person and an ever-present sense of community writers and sports fans have here.

Frank Sinatra once called Chicago “that toddlin’ town.” I always thought the lounge legend made up that word—toddling. But If I had to guess what it meant, I’d say it refers to our active and friendly nature and that in Chicago, you're always likely to find new friends ready to share good conversation.

Sportswriter/author Andy Frye has written for ESPN Chicago and Rolling Stone. His new book about Chicago, NINETY DAYS IN THE 90s, is out now.