It happens every year but unfortunately the best option is to sim the first year and really dig into the league the starting the second year. I have inquired and have received feedback from Matt and others that when the game is created all 29 AI GM's start the process of shaping the team they way they want based on the programming logic and it sorta defies what we (the player) would do.
Also, it has been stated numerous times that the AI doesn't see names and only sees the underlying ratings and stats based on the percentages you have set. The AI must balance the current season with its long term plan and for the most part the AI is not found of taking on long term salaries and will give up on players earlier than the player.
I just try and put myself in the shoes of the AI and ask if I would make the trade if I was on the other end. I usually handicap myself by severely limiting the number of trades per season (usually only 1 or 2 trades per year and only at trade deadline). This is more to make the game harder on me but with the improved AI the last few versions I haven't won a World Series since calendar year 2017 and I'm hoping the drought ends this summer.
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World Series championships: 1926, 1931, 1934, 1942, 1944, 1946, 1964, 1967, 1982, 2006, 2011
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