I think Maddon is deserving. Yes, he managed Cubs for a relatively short period, but he has that WS win, which not many Cubs managers have on their resumes, and is tied for lead with four playoff appearances. Only way Durocher should be on the list is if they are making a distinction between a manager and a player-manager.
Frank Chance with the other two WS championships is deserving, but he is on the team as a player, so he’s covered. Charlie Grimm is second on all-time wins list and led team to three post seasons, but some of those years were as player-manager.
Now that I’ve looked at the entire list of those on the team, the most glaring omission is Cap Anson (unless I missed his name on list). He’s the organization’s all-time winning manager. Even if you are saving the managers slots for those who just strictly managed during a season, Anson should be on as a player. He’s not only the first and last Cub to collect 3,000 hits, but he’s the first one in baseball history to do it. Oh, and he’s in the Hall of Fame. All of that occurred pre 1900, but don’t call it a 150 Anniversary team if not willing to go that far back.