Chicago Cubs March Madness Bracket- Elite Eight

1 of 5

Ernie Banks, Chicago Cubs (Photo by Chris McGrath/Getty Images) /

As we get used to this new (ab)normal without baseball or any other sports in April, here’s the Elite Eight of 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. Even though it’s technically April.

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.

We’re now into the Elite Eight portion of the Cubs tournament, so all the players have now become household names for even the most fairweather of fans. 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.

Billy Williams, Chicago Cubs (Photo by Focus on Sport/Getty Images) /

Chicago Cubs: Wrigley Regional Final Matchup

1 seed Ron Santo vs. 5 seed Pete Alexander
2 seed Billy Williams vs. 3 seed Fergie Jenkins

We’re down to the last two men standing in each region as the Elite Eight matchups are starting to come into focus. At this point, almost every name should be a gimme for every fairweather fan sitting around at home on the couch.

In the Wrigley Region, four legends squared off against each other, and one of the matchups even featured a pair of teammates most of our fathers remember fondly. In the first matchup, you have one of the most beloved Cubs of all time against one of the greatest pitchers of all-time- Santo vs. Alexander.

While they’re both Hall of Famers, Santo had a better career as a Cub, not to mention the fact that he announced games once his career as a player was over. Beloved both as an All-Star third baseman and a passionate announcer, Santo finds his way into the regional final in the Wrigley Region.

In the matchup of teammates, Williams and Jenkins make up probably the best matchup of the entire tournament. Both men have had their numbers retired and flown on poles at Wrigley, both spent the majority of their careers as a Cub despite playing with other clubs, and both have had a good relationship with the club since their playing career ended.

Even though Jenkins had more career bWAR than Williams, Williams was the better Cub statistically speaking- and he’s probably the greatest left-handed hitter ever to put on the blue pinstripes. Nod in a tight one goes to Williams.

That leaves us with No.1 seed Santo vs. No. 2 seed Williams in another tete-a-tete with former teammates.

Greg Maddux, Chicago Cubs (Photo by Jonathan Daniel/Getty Images) /

Chicago Cubs: Weeghman Regional Final Matchup

8 seed Greg Maddux vs. 5 seed Hippo Vaughn
3 seed Frank Chance vs. 2 seed Gabby Hartnett

In the Weeghman Region, Maddux continues his run through the bracket with a win against Vaughn. Again, despite his No. 8 seed going into the bracket, Maddux projects as a 1 or 2 seed because of his overall career. Maddux and his 355 career wins, four Cy Young Awards and 18 Gold Gloves just proved way too much for Vaughn despite being one of the best Cub players of all-time.

He will take on a guy from a century ago, as Chance narrowly edges Hartnett in the No.3 seed vs. No. 2 seed matchup in the bottom part of the bracket. While both players played in a completely different era of baseball, Chance gets the nod in an evenly matched showdown thanks to two World Series rings from 1907 and 1908. As all Chicago fans know, rings don’t grow on trees, and it took over a century for any Cub to lead his team back to the promised land.

That leaves us with No. 8 seed Maddux and No. 3 seed Chance meeting in the Weeghman Regional Final. As two of the most well-known names in Cub history, they’re beloved by many but are different players from totally different eras. No doubt, they could have flip-flopped and played in either era, given their talent and overall baseball acumen.

Ryne Sandberg, Chicago Cubs (Photo by John Reid III/MLB Photos via Getty Images) /

Chicago Cubs: Mesa Regional Final Matchup

1 seed Ryne Sandberg vs. 4 seed Mark Grace
2 seed Sammy Sosa vs. 3 seed Rick Reuschel

Well, look what we have here. This Mesa Regional Final matchup seems fated by the Baseball Gods, as the matchup of the two biggest Cub names of the last 40 years square off in the Mesa final. Top seed Sandberg took out his former teammate in Grace, even though there were several years towards the end of Ryno’s career where Grace was probably close to his equal on the field.

More from Chicago Cubs All-Time Lists

In the end, however, Sandberg had the better career overall and is now enshrined in Cooperstown. He probably also holds the title of the best overall player many modern Cubs fans have ever seen play. High praise considering some of the guys on the squad today.

Sosa took out Reuschel and now awaits Sandberg as the most prolific offensive player in modern Cub history. Of course, the Steroid Era of baseball taints and clouds much of his accomplishments, as well as the unceremonious way he finished out his Cub career. If not for those two blemishes, Sosa’s number 21 would be flying at Wrigley along with Sandberg’s. Sosa had 10 straight seasons of at least 35 home runs, hit 60 or more home runs three times, and single-handedly (well, maybe with a little help from Mark McGwire) resurrected the game of baseball in the Summer of ’98 when he won NL MVP.

Will No. 2 seed Sosa be able to take out the number No.1 seed in Sandberg? Stay tuned.

Ernie Banks, Chicago Cubs (Photo by Photo File/MLB Photos via Getty Images) /

Chicago Cubs: Catalina Regional Final Matchup

1 seed Ernie Banks vs. 5 seed Johnny Evers
3 seed Mordecai Brown vs. 15 seed Jake Arrieta

While the Catalina Region saw Arrieta advance a couple rounds with upsets, Brown played the role of Daniel Murphy in the 2015 playoffs, abruptly shutting down a magical run by the big right-hander. While Brown may not be as recognized by modern fans, any pitcher nicknamed “Three Finger” has to get some serious swag points in a matchup of pitching greats.

While Arrieta won 22 games the year before a World Series trophy was hoisted for the Cubs, Brown won 20 and then bested that with 29 in the 1907 and 1908 World Series years. Arrieta was only able to manage 18 the year the Cubs won it all in ’16.

Next. KB has an heir apparent. dark

In the top part of the bracket, Mr. Cub- Ernie Banks- continued his dominant run through the bracket, taking out Evers in a demolition.No.1 seed Banks moves on to face No. 3 seed Brown in the Catalina Final, pitting one of the best pitchers to ever wear blue pinstriped against the greatest Cub of all time. Game on.

As we edge closer and closer to the Final Four, keep reading and commenting/voting for your favorite Cub and your memories/thoughts about each.

Home / Chicago Cubs All-Time Lists