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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.

Cubs free agent target: Yuki Matsui

Could the Cubs find bullpen help from NPB?

A look at Cubs trades in the expansion era: 1993

A little bit of this, a little bit of that.

Should the Cubs trade Christopher Morel?

There are a lot of factors involved.

Ryan Flaherty is going to be named Cubs bench coach

He’s a former Cubs draft pick.

A look at Cubs trades in the expansion era: 1992

One VERY important deal was made in this calendar year.

Andre Dawson wants his Hall of Fame plaque changed to a Cubs cap — and the Hall is listening

Give the man what he wants.

A look at Cubs trades in the expansion era: 1991

This was a quiet year for trades.

Cubs trade target: Tyler Glasnow

The Cubs could use a starting pitcher. Here’s a good one.

A look at Cubs trades in the expansion era: 1990

A quiet year on the trade front.

Cubs free agent target: Josh Hader

Should they go for the longtime Cubs tormentor?