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Challenging idea
This can apply to either historical or fictional mode. I read it somewhere a long time ago from someone else and decided to try it out myself.
I started a historical league in 1901. The object is to start with the worst team historically (St Louis Browns) and manage that team until winning a WS. When you win the WS, you move to the worst team from that year. Move to your new team after all the awards have been handed out. Keep the process going until you win with every team. It's definitely harder than you would think especially with ratings turned off and only using stars. So far, I have won 8 in 38 seasons playing out all my games. It seems to be more difficult in the 1930's. The incoming rookie talent seems to be rather weak. My goal is to win with all teams before I run out of historical rookie imports.
If you do with fictional, I suggest simming a couple years to find the worst team. Attached a shot of my history. Having the worst time with getting a championship with the Giants. Starting 1937, I integrated the Negro League Players. I though I had a good enough roster to win, but I can't seem to put it together with this team.
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