Woody’s Winter Warmup 2020 Review

Kerry Wood’s Wood Family Foundation has been hosting a charity event titled, Woody’s Winter Warmup, since 2011. It is always held the first night of the Cubs Convention at Harry Caray’s. Usually, it has been held at Harry Caray’s on the 7th floor of Water Tower Place. A few events have been held at the Navy Pier location. 


In the past, my friend Dave and I, have rushed from the Cubs Convention opening ceremonies to Water Tower Place to get a spot in the front of the line so we can get a spot on the bar to be close to the celebrity bartenders.

Last year, the foundation began selling VIP tickets for an extra $100. The only added bonus for the extra $100 was an earlier entry 30 minutes before the general admission crowd was allowed inside. The general admission ticket is $250 and includes all you can eat and drink, plus tips to the celebrity bartenders. It’s for a great cause and the foundation does a fantastic job serving Chicago, and I’m happy to pay this price.​​

I felt that losing our spot on the bar would be a downfall, but it came with perks not being up front. Mainly, you sacrifice eating and using the restroom for the most part otherwise you lose your spot. It was less crowded in 2019, and you can read my review of the 2019 Woody’s Winter Warmup review. This year’s crowd was even smaller. That is nice, but I don’t want it to get too small at the risk of making less money for the foundation and it ceasing to exist. 


While we waited in line, an older lady walked into the VIP check in and was greeted by the host. He mentioned, “how does it feel to have your name up there?” It was Dutchie Caray, Harry Caray’s widow. I had to meet her, and spent a short amount of time talking with her. She was very gracious and took a picture with me.

​​Carlos Zambrano was one of the first celebrity bartenders.​​Cubs pitcher Adbert Alzolay was also serving up drinks. I loved the shirts they made for bartenders this year: “Warm Up. Tip More.” ​​Another current Cubs player behind the bar was David Bote.


​​And Albert Almora also served us. ​​Even former Cubs were in attendance. Bob Howry, Mike Remlinger, and Jon Lieber could be seen mingling throughout the night. Ted Lilly and Reed Johnson took a turn behind the bar.​​

The music is always great. Jim Peterik from Survivor performed “Eye of the Tiger,” and still sounds great. 


My favorite each year is Tom Higgenson, lead singer from the Plain White T’s, performing, “Hey There Delilah.”

As you can see by the smiles on our faces, we always have a great time at Kerry Wood’s Woody’s Winter Warmup. Pictured here include my friends Stewart McVicar, owner of Club 400, and his Club 400 Podcast partner, William Geheren. ​​Thanks, Wood Family Foundation for another great night. 

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