Woody is essentially the middleman between the manager and the Glazers. The problem is that he's on the Glazers' side.
Summer 2019
Ole: The team is a mess. We probably need as many as 5 solid additions to the starting XI if our goal is to challenge for titles.
Woody: Ok, I'll give you 40% of that. Here are 2 defenders and an unproven Championship winger.
Ole: We have problems in midfield and attack as well, though?
Woody: What was that?
Ole: N.. Nothing! I guess if Pogba can stay injury free we may reach top 4...
Woody: Now that's what I'm talking about!
*Pogba gets injured*
*Total disaster ensues*
January 2020
Woody: *sigh* Ok, I'll give you 60%! Here's Bruno and a backup striker from the Chinese league. Better hustle now, boy!
Ole: Oh gee! Thanks, Mr. Woodward!
*finishes 3rd after a miraculous comeback*
Summer 2020
Ole: I did OK, no? Could I maybe get the remaining 40% now? And maybe some bench options but that's not the most imp...
Woody: Sold to the man who looks like Gollum!
Ole: Oh boy, I can't wait! Finally United will have a starting XI that kind of looks like a United team!
Woody: Actually, I'm only giving you 40% of your current request. I figured that translates to some bench options. See you January! If you still have a job, hehehe.
Bollocks. How about.
Woodward: Ole we have transfer budget of £ £ £ we would like you to achieve top 4 with that.
Ole: Ok, I want you to buy me Maquire.
Ed: Maquire will cost 80m making him the most expensive defender ever and will use up most of your transfer kitty meaning you wont have much to spend on other players, are you sure about this have you got any other alternatives?
Ole: No thats OK I still want you to get me Maquire. oh and AWB and James
Ed: ok who is this James? is he really good enough for United?
Ole: Yeah dont worry about it I know what Im doing.
Ed: ok.
Ole at Christmas: I know I said I could achieve top for with those transfers but I made a mistake please also get me Bruno.
Ed: What? ffs thats another 40m! Ok Ole.
Ole: this summer I want to break the transfer record again.
Ed: haven't you got any alternatives? That's a lot of money to spend with our stadium being empty etc.
Ole: no not really.
Ed at end of transfer window: Ole I told you we cant afford Sancho what the feck are you doing? where are your alternatives?
Ole on the last day panicking: get me any of the players we have been scouting and a striker
Ed: will Cavani Pelestrini and traore and telles do? they are all that are available right now on deadline day
Ole: yes get them
See we can make up any story we want cant we? Fact is though Ole is responsible for his budget and his transfers as he should be he is a manager not a coach.