#1: Nothing left to Chance
There is no doubt who stands atop the Chicago Cubs manager totem-pole. Frank Chance is the only one worth of such a spot. In eight seasons, he accumulated 768 wins, good enough for third in team history. No Cubs’ manager has a better winning percentage, and only Maddon can boast the same average division rank.
But, here are things no one else can say. Never did he win less than 91 games in a full seasons. Okay, so he won 55 in 1905, but he only managed 90 games. His winning percentage never went below .597. His teams won four pennants and two world series.
Oh, and he was a player on every team as well. Not just any player, but one in the Hall of Fame. His career WAR places him 13th on the team all-time.
Wait, there is more. He did all of this before the age of 35. You have that right. Ben Zobrist is older now than Frank Chance when he ended his career. Maybe it was a different game back then, but it was still 152 games in a season. Since 1912, no Cubs manager has come close to performing like Chance.
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But, if Maddon stays for a few more years and wins another title, we could adjust this list. There is no doubt, however, that Chance and Maddon are the best Cubs managers in the Modern Era.