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Playing the games individually probably wouldn't help much since the computer is managing the other teams, although I personally think it's more fun to manage the games yourself, but it's quite time-consuming.
I can think of 3 possibilities:
1) Your record is just bad luck. There's a random element in how the players perform.
2) Your team may not be as good as you think. The scouts don't always rate the players accurately. Maybe your bench manager and coaches aren't very good.
3) there's something faulty in how you've set up your lineups: wrong people in the starting rotation, wrong guy as closer, wrong guy leading off, pitchers pitching when they're tired, etc. You could try letting the computer manage the lineups, but where's the fun in that. Go to the info page on the team screen. Try to figure out what the problem is. Is it pitching, hitting, or both.
Don't be discouraged. It's probably difficult, if not impossible to take a mediocre team like the Cubs and trade your way to a pennant in one season.
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