Every deal involves an element of risk. Offering a historically injury prone 30 year old a long term deal was a gamble. It's much the same with Ilkay Gundogan and Riyad Mahrez - I've not checked, but I'd be surprised to see either with a contract up to 34.
With age comes slower recovery, and that's what we're seeing evidence of now with KDB.
There's a wise saying.... Only gamble if you can afford to lose. The City Group can afford it, so they see it as lower risk.
You refer to the 'professionalism' of decision makers... It's their job to assess risk as part of making any deal, the same as any line of business. Sometimes they get it right, sometimes they don't. If they get it right with KDB, that's great. If not, we may end up with an expensive passenger for 2 or 3 seasons.