Chicago Cubs March Madness Bracket – Round of 32

As we settle into shelter at home and quarantined states across the country, here’s the first round of matchups and how our favorite players fared against one another in the March Madness, Chicago Cubs Edition.

Without any semblance of Chicago Cubs sports or normality in American society currently, it’s hard to be excited about the prospects surrounding much of anything right now. That being said, we’re here to keep you entertained and add some happiness to your day. What better way to do such a thing than to give you a little bit of Cubs baseball history and a tie into the best tournament of the year? March Madness.

Regardless of your knowledge of the Chicago Cubs, this is an opportunity to get to know some of the greatest Cubs of all time, their eras, their stats, and what kind of players they were. It’s also a way to pit modern versus old school players in an attempt to settle who is the GOAT in Cubs history.

When designing the brackets, the parameters were pretty simple. Using career bWAR for all players, the bWAR is a total amount of bWAR garnered during a Chicago Cubs. Note that some of the players would be much higher if their career bWAR with different teams were used, but that may or may not come into play when we start having these players square off against each other to determine how they advance through the bracket.

For now, the object is to rank all of the players, create 1 through 16 seeds, and then set up matchups in four different regional brackets. For more significant fan input and to have your voice heard about who should win each matchup, please comment and make your picks on both the Facebook and Twitter links to this specific article. And, of course, check back as we progress through the bracket.

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.

Chicago Cubs: Mesa Region

• 1 seed Ryne Sandberg defeats 16 seed Pat Malone
• 8 seed Bob Rush defeats 9 seed Lon Warneke
• 12 seed Aramis Ramirez defeats 5 seed Billy Herman
• 4 seed Mark Grace defeats 13 seed Bill Lange

• 6 seed Carlos Zambrano defeats 11 seed Woody English
• 3 seed Rick Reuschel defeats 14 seed Frank Schulte
• 10 seed Andy Pafko defeats 7 seed Jimmy Ryan
• 2 seed Sammy Sosa defeats 15 seed Dick Ellsworth

More from Chicago Cubs All-Time Lists

• Ranking the 5 best switch hitters in Cubs history
• Who are the 5 best players drafted by the Chicago Cubs?
• Recalling the 5 best-hitting pitchers in Chicago Cubs history
• Chicago Cubs: 5 loudest moments in Wrigley Field history
• Chicago Cubs: Ranking the team’s 3 worst trades of the last 50 years

Two upsets out of Mesa include more modern Cub favorite Aramis Ramirez and four-time All-Star from the 1940s and 50s, Andy Pafko. Ramirez was one of the most consistent and productive Cubs for his almost decade with the club after coming over from the Pittsburgh Pirates (along with Kenny Lofton) for Jose Hernandez, Bobby Hill, and Matt Bruback.

After the results from the first round, here’s how the Mesa region stacks up now:

• 1 seed Ryne Sandberg vs. 8 seed Bob Rush
• 12 seed Aramis Ramirez vs. 4 seed Mark Grace
• 6 seed Carlos Zambrano vs. 3 seed Rick Reuschel
• 10 seed Andy Pafko vs. 2 seed Sammy Sosa

There are a ton of modern era Cubs players in this batch, and the bottom part of the bracket has two great modern Cubs who left things on shaky ground at the end of their careers due to poor choices and off-field incidents. Then you have Ryno staring down a potential matchup in the next round with the guy he stood next to for a decade in the late 1980s and 1990s.

Chicago Cubs: Catalina Region

• 1 seed Ernie Banks defeats 16 seed Ryan Dempster
• 8 seed Claude Passeau defeats 9 seed Ed Reulbach
• 5 seed Johnny Evers defeats 12 seed Heinie Zimmerman
• 4 seed Bill Hutchison defeats 13 seed Tom Burns

•  6 seed John Clarkson defeats 11 seed Kiki Cuyler
• 3 seed Mordecai Brown vs. 14 seed Derrek Lee
• 10 seed Bill Hands defeats 7 seed Bill Dahlen
• 15 seed Jake Arrieta defeats 2 seed Stan Hack

The big upset in this region is the 15 seed, Jake Arrieta, taking out the two seed, Stan Hack. Arrieta takes out Hack on the strength of one of the greatest seasons in MLB history in 2015, capped off by a Cy Young Award, and then a World Series with the Cubs in the following year. While he wasn’t quite as good for the entirety of the 2016 campaign, the first half of the season followed up his Cy Young year with much of the same, including another no-hitter against the Reds on April 21st.

10 seed Bill Hands also defeated seven seed, Bill Dahlen, in the only other non-chalk outcome in the bracket. Derrek Lee put up a fight in his matchup with Hall of Famer Mordecai Brown, but alas, one of my favorite players of the 2000s was no match for a guy who put up 20 wins in six straight seasons and now sits in Cooperstown.

With the outcomes of the first round in the books, here’s what the Catalina bracket now looks like:

1 seed Ernie Banks vs. 8 seed Claude Passeau

5 seed Johnny Evers vs. 4 seed Bill Hutchison

6 seed John Clarkson vs. 3 seed Mordecai Brown

10 seed Bill Hands vs. 15 seed Jake Arrieta

Going forward, it’s clear that Mr. Cub, Ernie Banks, has a clear path to the Final Four, but some old-timers might have something to say about that along the way.

Keep commenting on Twitter and Facebook for who you want to see advance, and check back next week for the next round of matchups to know how the Cubs March Madness bracket shakes out.