Raiola’s cash till has been ringing ever since. More than £40million from Paul Pogba alone, another eight-figure sum for Zlatan Ibrahimovic and over £3m for Henrikh Mkhitaryan.
He has put Jorge Mendes’ nose out of joint by dislodging the publicity-hungry Portuguese super-agent as the Red Devils’ preferred supplier.
Raiola, routinely insulted by agents in the game who refer to him as “the Fat Pizza waiter”, has become United’s go-to man.
Botched deals on Woodward’s watch for Cesc Fabregas, Pedro, Gareth Bale, Thiago Alcantara and Sergio Ramos have worked in Raiola’s favour.
When Raiola is peddling players, United are always in the mix.
To be fair, he has accumulated a stellar cast list — Pogba, Ibrahimovic and Mkhitaryan are three of the biggest names in the game.
The Italian-born Dutchman is also working on deals way down the line, with United eager to have first option on some of his other emerging young talent.
For that privilege, Woodward has had to pay the big bucks.
Romelu Lukaku, who is refusing to commit to a new contract at Everton worth more than £100,000 a week, is another Raiola client.
United, in the hunt for a new striker because of the injury to Ibra, have already put down a marker.
Gianluigi Donnarumma, the 18-year-old AC Milan keeper, is also on United’s radar as they prepare for David De Gea to finally join Real Madrid.
Donnarumma is another in Raiola’s stable. As is Juventus’ 17-year-old Moise Kean, already the first Champions League player born after January 1 2000 and currently starring in the European Under-17 Championships in Croatia.
Milan, sixth in Serie A and in danger of missing out on a place in the Europa League next season, are struggling to hold on to their highly-regarded young keeper.
It puts United in a strong position, relying on their relationship with Raiola to make sure they get first bite at the cherry.