They won the division 3 out of 6 years between 2003 and 2008....
Good for them. They also won 90 games just once during that stretch, and also saw that pipeline of young talent that provide the initial fuel for that run to whither up and die out almost completely.
This is the first time I was asked to - so using the word "yet" is a bit premature.
Giants
Athletics
Mid 90s Yankees
First I will apologize because I was confusing this narrative you've provided with another aptly named poster that I asked for that example. So you are correct that was my mistake this is the first time I have asked you for that example.
Now for your example the Athletics (26) have one of the worst farm systems in baseball right now. The A's were last ranked above the lower third of baseball in 2012, right after they were finishing up a run of 5 years at .500 (1 season) or below. The Giants (20) aren't much better, and they haven't been ranked any higher than that since 2010. Seems like they haven't managed to win and maintain that farm system.
The Yankees example fails on a number of levels. First of all you are making an apples to oranges comparison between teams built under the old CBA versus this system. Second of all the Yankees farm system was great starting in the early 90s, and yes they maintained that good farm system. But it was not built while they were winning. The Yankees dropped out of the top 10 once all the way down 12 in 97, but that is the point that I was trying to raise about the difference between those organizations and the Cubs. While they were winning they still kept the farm system going instead the Cubs did very little to add to the farm while they were "winning" under Hendry.