Blake Peters is no stranger to clutching up in the biggest of moments. So when he stepped on the court in the second half of last Sunday's Round of 32 contest against Missouri, he was ready. 17 points and one more giant upset for the Cinderella 15-seed Princeton Tigers later, and Peters could add another moment to his long list of clutch performances: helping his team to the Sweet 16.

Throughout the past month-and-a-half, Chicago Sun-Times high school sports contributor Joe Henricksen has been counting down the 50 most winningest Chicagoland boys basketball teams of the decade (the...