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Al Yellon is a native Chicagoan who has been following Chicago sports since the 1960's. That means he's seen a lot of losing -- but finally enjoyed the ultimate triumph, the Cubs World Series title in 2016. He left Chicago to go east for college at Colgate University, then returned and worked for 29 years as a television director for Chicago TV stations before joining SB Nation full time as a senior editor.

Should the Cubs retire Jon Lester’s number?

Opinions differ. I’m on the fence.

MLB made a labor agreement proposal to players. It didn’t go well

It won’t be long before part of the 2022 season is in jeopardy.

Wrigley Field historical sleuthing: 1938 aerial edition

There’s a lot you can find from just one photo, beyond what’s happening on the field.

Is Jon Lester a Hall of Famer?

The answer might not be as simple as you think

Cubs historical sleuthing: Dizzy Dean edition

This one doesn’t appear to have many clues... but it was actually pretty easy.

MLB players and owners will meet Thursday. What does this mean for the 2022 season starting on time?

NARRATOR: "Everything... and nothing."

Jon Lester has announced his retirement

Thanks for everything, Jon. Including the beer.

Cubs historical sleuthing: Rick Monday edition

This was a tough one.

The Chicago Bears mess is reminiscent of the Cubs under the Wrigleys

The Chicago NFL franchise’s leadership is playing out like the end of the Wrigley regime

Cubs historical sleuthing: Ron Santo and Roberto Clemente edition

When did this play involving two future Hall of Famers happen?