I got the sense that McHale's job was to get the stadium built and to act as the liaison with the league because Ilitch was still sort of an outsider. McHale's got a family history in the game.
I've said before that the strategy in the mid 90's wasn't flawed. You had McHale, Smith, and Buddy Bell all as legacy people running the team. Not a bad way to go. I wonder how things might have gone had they not built such a silly ballpark to begin with and never made the Juan G trade.
There was also the issue of payroll issues. Rumors were the team had to get a loan from the league.