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 in January! If you still have a job, hehehe.