He is a very shrewd operator, and Rooney has become hugely reliant on him. Take the example of Rooney going to buy a £40,000 puppy with his wife, Coleen, filmed as part of Rio Ferdinand's comedy series a few years back.
"Can we get it?" begged Coleen of Wayne.
"I'll have to ask Paul," came the reply.
It's a story that illustrates their relationship and one that makes me certain Rooney will end this transfer window as a Chelsea player. It might not happen until deadline day, but it will happen.
He's not happy at United. Stretford knows this, and he knows it's time to move his player on. He tried before, in 2010, and Rooney came a lot closer to joining Manchester City than you might think. Only the Manchester graffiti and the threats of the hoodies stopped that one happening.
This time he'll succeed, with Chelsea and Jose Mourinho the benefactors, and Rooney will be a better player for it. He's gone stale at United, and he clearly doesn't like the fact Robin van Persie is now their top man.
Stretford will have told Rooney his choices early on. Only City, PSG and Chelsea could pay him the kind of money he wants. Rooney has chosen Chelsea, and Mourinho seems prepared to wait until late in the window to get his man. Rooney is his only target now.
It's the perfect time for Rooney to move on, and David Moyes will ultimately be left with little choice other than to sell. He can't afford a demotivated Rooney in his squad and—unlike Liverpool with Luis Suarez—Moyes cannot guarantee he'll get 100 percent from Rooney if he stands in the way of his wishes.
My guess is United will push the fee as high as they can and throw it all into a bid for Cesc Fabregas. There's no like-for-like replacement for Rooney on the market and all of the big-name strikers have done their deals, so it'll be an attacking midfielder they go all-out for.
Gareth Bale is not an option. If United were going to bid that kind of money they'd put it into trying to get Cristiano Ronaldo back, which isn't happening either. But they desperately need to make a statement before the window shuts.
My concern with United is that David Moyes lacks the kudos and credibility to attract the truly big names. Players who would have gladly come to play under Sir Alex Ferguson will be Googling Moyes' record to find he's won just one trophy in his managerial career—and the Community Shield, at that—unless you count the Second Division (third tier) title.
Will Rooney join Chelsea before the window closes?
He needs to make something happen. He's got a lot of young attacking players with potential in his squad—the likes of Wilfried Zaha, Danny Welbeck, Shinji Kagawa and Co.—and some who played beneath themselves last season, most notably Nani. If he loses Rooney, he'll lose creativity and goal threat from midfield.
Moyes will have to act to remedy that.
I already had Chelsea as title favourites, and with Rooney added to their squad I'm convinced they'll be the team to beat. I can see Mourinho using him in the three behind a main striker. He has strong options in Fernando Torres and Romelu Lukaku up top, and Rooney should settle in quickly alongside his England teammates Gary Cahill, Ashley Cole and Frank Lampard.
Stretford will have already told him all of this, of course. He'll have sold the Chelsea move in every way possible, and Rooney will have listened.
United won't want to lose Rooney to a title rival, but if Chelsea is where he wants to go and the Blues are prepared to pay a huge sum for him, Stretford will find a way of making it happen. That's what he does.
Stan was speaking to B/R's Will Tidey