Here's the timeline:
Ilitch bought the team in August of 92. From then you had a mess of Joe McDonald, Jerry Walker, and Joe Klein. Then McHale brought in Randy Smith who was well thought of and came from a baseball family.
I actually don't think he hung on to Smith too long. The team came close to .500 after being decrepit for most of the 90's. Randy was here for 6 full seasons, you give him a pass on the first few, then the team flirts with .500 in 2000. After the lousy 2001 season Ilitch hires DD as President and CEO which we all knew meant he'd be GM at some point and sure enough a week into 2002 Smith is fired. I think that's about right. You should count the hiring of DD as Smith's axe. Let DD see what he has to work with and let him make the call for his reasons.