Mourinhos already had a few chances at signing the right player for CB so can you blame Woodward if he is hesitant about mourinhos choices for this summer
Bailly, Lidelof, Jones and Smalling were set to be our roster of CBs this season. That 4 for 2 places, which would ordinarily be fine. The problem is that they're so injury prone, you need at least 5 options to get through the season. Mourinho is rightfully asking for another option. It's not an illogical request. As it is, we're going to have to keep Rojo as the fifth senior CB to provide cover. Not ideal when he's as rash as they come.
The £100m transfer kitty also applies to other areas of the pitch. Woody's stuck in a Football Manager headspace if he believes that superstars are the only worthwhile additions to the team. Jose's won the CL with lesser individuals who have adhered to his philosophy, so he should be afforded the same kinds of acquisitions here. You're handicapping him if you don't and that can only hurt MUFC.
On balance, Mourinho is a proven winner as a manager, but Woodward is not a proven winner as a football Chief Exec. So the latter undercutting the former is detrimental to Manchester United. If it were an experienced and successfull CE (like Gill), I'd maybe have a bit more sympathy. But Woodward's track record doesn't afford him that leeway. His failures are too many to excuse. Mourinho may have made some missteps as well, but he's made enough good decisions to be given the benefit of the doubt. Otherwise, there's no point in keeping him as manager.
Incidentally, I didn't want Mourinho before he signed. But whilst he's here, I'm going to back him as he tries to mould the team in his image. He's one of the best squad builders around. Even when his philosophy doesn't quite work, he knows how to get the right players in to fit any style. The next manager will do better with a Mourinho squad than a squad left behind by almost any other manager. Hell, even Avram Grant got to a CL final with one.