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Chicago Cubs: Wrigley Region
- 1 seed Ron Santo vs. 16 seed Jack Taylor
- 8 seed Anthony Rizzo vs. 9 seed Hack Wilson
- 5 seed Pete Alexander vs. 12 seed Riggs Stephenson
- 4 seed Joe Tinker vs. 13 seed Kris Bryant
- 6 seed Bill Nicholson vs. 11 seed Kerry Wood
- 3 seed Fergie Jenkins vs. 14 seed Rick Sutcliffe
- 7 seed Ned Williamson vs. 10 seed Bill Lee
- 2 seed Billy Williams vs. 15 seed Fred Pfeffer
The Wrigley Region is home to some of the biggest and most recognizable names in Cubs history, including its modern history as well. With the likes of Santo, Jenkins, Williams, Wood, Wilson, Rizzo, Bryant, and Sutcliffe, this region will pit some of the best Cubs of all time against one another.
While Bryant and Wood are underdogs in this bracket, there’s no telling what happens once March is upon us. It’s hard to think anyone will oust Santo or Williams before they meet in the Elite Eight, but there could be some upsets along the way. While most Cubs fans know exactly who and what Santo was, for those of you who don’t, Santo slugged 337 home runs and drove in 1290 RBI in his 15-year career (all with the Chicago team as he played his final season on the southside).