The greatest free agent signing in the history of Chicago sports announced his retirement Wednesday morning.

There were a lot of moves that Theo and company did to get the Cubs their first World Series title in over a century but it all started with signing the big lefty to anchor the starting rotation.

And what an anchor he was. Lester brought confidence and swagger to the north side, the kind of confidence and swagger a player can only achieve by already having two World Series titles under their belt.

There are hundreds of highlights I could put in here but I'll bring you my two favorites from Lester's time with the Cubs.

The first was him doing an interview after the Cubs clinched the an NLDS win in 2016 after drinking what must have been at least a dozen beers if not more.

I say "if not more" because Lester is a man that likes to drink. Remember he was part of the chicken and beer scandal when he was with the Red Sox. The man likes to throw back a few, and when you're on pace to win over 200 games in your career and 3 World Series rings, that's ok.

That video is only 45 seconds long but has at least 8 laugh out loud moments. My top three are:

  • It's not all peaches and roses, or however the saying goes.
  • Our guys are cocky, they don't give a s#%t. I'm sorry, apologize.
  • "Jon, what makes this winning clubhouse so special?" Lester: "Uh, winning" [flashes a VERY drunken smile]

That interview is the embodiment of Work Hard, Play Hard. Lester worked as hard as anyone and obviously loved to blow off some steam.

He also had a sweet boat that he liked to party on in Lake Michigan's harbor.

My other favorite Jon Lester moment was when he made Tim McCarver look like an absolute idiot.

Tim McCarver was the first sports announcer that I realized I didn't like. That was when I was about 12 years old. Seeing Lester figuratively shove it directly into the former Cardinal's face is something I'll randomly think about at least once a month.

Thanks for the memories Jon! You probably will never have to buy another beer in Chicago for the rest of your life.

LOOK: Best Beers From Every State

To find the best beer in each state and Washington D.C., Stacker analyzed January 2020 data from BeerAdvocate, a website that gathers user scores for beer in real-time. BeerAdvocate makes its determinations by compiling consumer ratings for all 50 states and Washington D.C. and applying a weighted rank to each. The weighted rank pulls the beer toward the list's average based on the number of ratings it has and aims to allow lesser-known beers to increase in rank. Only beers with at least 10 rankings to be considered; we took it a step further to only include beers with at least 100 user rankings in our gallery. Keep reading to find out what the best beer is in each of the 50 states and Washington D.C.

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