Chicago Cubs March Madness Bracket- Elite Eight

Sammy Sosa , Chicago Cubs (JOHN G. MABANGLO/AFP via Getty Images)
Sammy Sosa , Chicago Cubs (JOHN G. MABANGLO/AFP via Getty Images)
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Billy Williams, Chicago Cubs (Photo by Focus on Sport/Getty Images)
Billy Williams, Chicago Cubs (Photo by Focus on Sport/Getty Images)

Chicago Cubs: Wrigley Regional Final Matchup

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.

Schedule