I imagine that rolling up scads of bad long-term contracts that would be a millstone around the franchise during the new owner's term might not have been that great for sale, though....
I suppose it also may be that Hendry was given money and encouraged to spent it to help the team, but that they didn't explicitly tell him to use it on bad contract and bad players? He might have came up with that notion on his own?
Watch the video of Joe Ricketts which I posted, or just read the transcript of it, which I also posted. It is clear that Tom Ricketts was not bothered by those contracts, and in fact thought they were for "the right players." The 2007 and 2008 seasons were window dressing. And, yes, someone who followed the game a bit more closely than the Ricketts clan would have known that.... but the Ricketts clan did not.
As to the "bad players" part of your comment, they were not bad at the time. The contracts were bad, but any time a team makes a major effort to produce a major improvement via the FA market, the later years are going to be painful. As I recall, very few here complained about the approach or the contracts at the time, because so many wanted to win quickly. We are suffering the consequences of that.
I understand that virtually anyone can pick any dozen moves Hendry made, or did not make, and assign blame and attribute the move to stupidity and blame him for the current mess, and there is no question that the mess is of his making, but the primary problem is far less how good or bad any individual moves might have been, but instead the natural consequences of the 2006-2007 spending spree as the team was going to get good fast.
I thought it was misguided then, because it seemed to me that the consequences we are now living with were quite likely, but my goal was to see the Cubs field a strong team for several years running, and and not to gussy up a pig to bring a better price at auction.