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Maybe part of the problem is that there's no "stop annoying me" factor to the game. You could theoretically send out trade offers to a team about a player you want, lowball them all to hell, and slowly work your way up in terms of what you're offering until you get to the bare minimum the AI will accept to complete a trade. In real life, GMs do do that, but the end result is that the guy on the other end of the line will catch on to the game and start grossly over-valuing the player in question because it's obvious you want the guy, and if you're going to play games with him, well, you deserve to be the result of some play yourself.
Actually, this happens a lot in online/multi-player leagues as well. Seasoned owners will try and trip up the "noobs" by offering vet-for-lots of prospect deals, but they won't do that sort of things once you catch on because... well, it's like going into a pawn shop. If you see a guitar grossly overpriced, you know the people who run the store don't really understand the value of musical equipment and as a result you're bound to find a bargain somewhere in there. Similarly, if you make a habit of trying to put one over on someone with every trade, someone's going to see your angle and take advantage of it.
Can this be fixed with AI? The way I'd do it is with the "bad boy point" thing I keep bringing up. But outside of that, bear in mind that it's not such an easy thing to implement, I don't think. Explaining it is hard; imagine how tough it would be to code.
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