Chicago Cubs March Madness Bracket – Round of 32

Chicago Cubs: Wrigley Region

• 1 seed Ron Santo defeats 16 seed Jack Taylor
• 8 seed Anthony Rizzo defeats 9 seed Hack Wilson
• 5 seed Pete Alexander defeats 12 seed Riggs Stephenson
• 13 seed Kris Bryant defeats 4 seed Joe Tinker

• 11 seed Kerry Wood defeats 6 seed Bill Nicholson
• 3 seed Fergie Jenkins defeats 14 seed Rick Sutcliffe
• 7 seed Ned Williamson defeats 10 seed Bill Lee
• 2 seed Billy Williams defeats 15 seed Fred Pfeffer

While there were only two upsets in this region, they skewed towards more modern players. In the 4-13 matchup, one Cub World Series hero (albeit a century apart!) took down another as Kris Bryant took on Hall of Famer Joe Tinker and scored the upset. While it’s an upset on the surface, Bryant has a long way to go in his career and could one day surpass Tinker in terms of total bWAR with the Cubs if he sticks around.

Kerry Wood, a fan favorite as a player who has seemingly become even more endearing to the Cubbie faithful in recent years, was the other upset in this region as he took out 1940’s era outfielder Bill Nicholson in a tough 6-11 matchup.

This means the bracket now looks like this:

• 1 seed Ron Santo vs. 8 seed Anthony Rizzo
• 5 seed Pete Alexander vs. 13 seed Kris Bryant
• 11 seed Kerry Wood vs. 3 seed Fergie Jenkins
• 7 seed Ned Williamson vs. 2 seed Billy Williams

With Santo and Williams still left, this region is still theirs to take, but the Bryzzo combination is looming in the top part of the bracket, and there’s a great pitching matchup between Hall of Famer Jenkins and 20 strikeout wunderkind Wood in the 3-11 game.