The AI does a pretty good job of running a team in OOTP. Sometimes there's a bad trade, but I haven't seen a team run into the ground year after year. The AI might do a bad job one year, then make a few good trades the next.
If anybody knows of a real life professional league that doesn't make bad trades, please point me to it and I will quickly become a fan.
Sometimes when we look at OOTP and think something is off, we need to step back and look at the "Big Picture" as well. Yes, the AI made a couple bad trades this year, but in general is the team improving overall? Is the AI headed in a good direction or bad direction with the team?
That's what I look at, and I just haven't seen the AI mis-manage a team to the point of ruin. Sometimes it takes a couple years before I can really see what the AI is doing. Sometimes it takes 2 bad trades and 3 good ones to get going in the right direction, but it always does from my experience.
Now - compare that to real life.
