Chicago Cubs Madness has come to the semi-finals

Chicago Cubs: Wrigley vs. Weeghman Regional

• 1 seed Ron Santo vs. 8 seed Greg Maddux

At this point in the tournament, you just can’t go wrong with who wins and loses. Period. All four teams stars left indelible marks not only on the Chicago area and ballclub but across all of baseball. All four are Hall of Famers enshrined in Cooperstown, and all four hold a special place in Cubs lore and history.

As is fitting for the teams most of the past century, none of them had much postseason success. And, while Greg Maddux did win a World Series in his time with the Braves, many feel that the Braves team did a lot of underachieving as well despite their stacked rosters through most of the 1990s.

In our first semifinal matchup, Santo takes on Maddux in a lopsided seeding contest. As the only guy who isn’t a one seed (due to his years with the Braves), Maddux seems a bit out of place. Yet, to anyone who ever saw him pitch, it’s abundantly clear that he belongs. However, while he belongs, Santo continues his run right through Maddux and the rest of the Cubs Madness bracket so far- all the way to the championship.

Chicago Cubs: A personal conundrum

I admit that this is a bit personal for me, but my love of the game and appreciation of the Cubs comes from my dad, who grew up in Chicago in the 1960s and 1970s. He grew up on Santo, Ernie Banks, Billy Williams, Fergie Jenkins, Don Kessinger, and Randy Hundley. Me- well, I great up on Ryno, Hawk, Mark Grace, Shawon Dunston, and Maddux. That being said, Maddux left after the 1992 season- right in the middle of my formative adolescent years.

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

Instead of watching Maddux lead the Cubs to the playoffs on WGN, I had to watch the arguably the greatest pitcher of my generation pitch on TBS (Roger Clemens, Randy Johnson, and Pedro Martinez could all get in that argument, but none of them pitched for the Cubs, so we’ll just leave that right there).

While Maddux is probably the greatest Cub pitcher of all-time, and he’s the last man standing in our bracket, he just doesn’t carry the same gravitas and weight as someone as venerated as Santo. My dad tells stories about Santo and Banks and Williams from his childhood, and I can’t think about Maddux in the same way. Maybe this will change in 50 years, but for now, Santo is onto the final matchup, I guess there’s a reason there’s a statue of him outside Wrigley Field, right?

Chicago Cubs: Mesa vs. Catalina Regional

• 1 seed Ryne Sandberg vs. 1 seed Ernie Banks

In much the same way as the other semifinal matchup, the Sandberg- Banks showdown is a fight for the ages. Well, different ages and eras, at least. For baby boomers, Ernie Banks will always be Mr. Cub, the greatest living Cub, and the face of the organization.

For the kids of those same boomers, Ryne Sandberg might very well be the greatest living Cub they ever saw. Take another step, and you have the Kris Bryant and Javier Baez question as well, but we’re not there yet with those guys- they still have a long way to go and neither even have a long-term deal with the Cubs in place at the moment.

Back to Banks and Sandberg, you just can’t go wrong with the choice. As young players, both could do just about anything on the ballfield- run, hit, field, hit for power, and play the game hard. They were both beloveds by fans because they were good and because they played the game the right way.

Banks was also the first black player ever to don the royal blue pinstripes and could have added a couple more years to his career if not for his time in the Negro Leagues and his time serving in World War II.

Sandberg doesn’t have those distinctions, but losing to Banks in this matchup of legends is nothing to scoff at. Losing to the guy who is the face of the team and one of the best players ever to play the game is sort of like Lebron being the second-best basketball player of all time. Yes, you read that correctly- that fact shouldn’t get me in too much trouble on a Cubs blog, right?

There’s a reason there’s a statue of Jordan outside the United Center, just like there’s a reason there’s a statue of Banks out in front of Wrigley Field. They don’t generally build statues for second best.

Stay tuned as we look at the matchup of the two greatest Cubs of all time- Banks and Santo- in an unforgettable Cubs Madness championship. What a tournament!