The worst kept secret in football has finally been revealed as it’s now been confirmed that Pep Guardiola will be heading to Manchester City this summer.
But where does that leave Manchester United?
Due to lack of excitement, to an early Champions League exit, and a limp Premier League title challenge could spell the end for Louis van Gaal at the end of the season and if that actually happens, United supporters seem to be demanding only for one man.
City have upped the ante, so do United rip up their long-standing Giggs strategy and go for Mourinho, on the basis that if you can't beat them, join them?
Though the final decision will rest with the Glazer family rather than Woodward, his input is extremely important. What to do next will be eating away at him.
On the face of it, there is only one figure who can match Guardiola for glamour, charisma and power. That's Mourinho.
Their rivalry in Spain signalled the lowest point in relations between Barcelona and Real Madrid.
'He can have his Champions League outside the field. Fine.' retorted Guardiola to Mourinho's taunts.
The self-styled Special One also prodded Barca assistant-manager Tito Vilanova in the eye during one heated Clasico.
That kind of behaviour will make some United legends, Sir Bobby Charlton among them, queasy. But others will like the idea of getting under City's skin, up to the point of physical confrontations, of course.
Former chief executive David Gill was always of the view United needed a course-and-distance winner in charge rather than a novice.
Since Sir Alex Ferguson retired, Woodward has seen Manchester City assemble the better team and win more trophies. With Guardiola coming, City will enhance their popularity worldwide, they will become the coolest club in Manchester. It is a situation that leaves the executive vice-chairman in a cold sweat.
Yet, while the obvious knee-jerk reaction would be to fast-track Mourinho into the club for next season, it's not that simple.
Woodward is intelligent enough to realise that despite his incredible CV, Mourinho is no longer the guarantee of success he once was. And if he screws up again at Old Trafford like he did at Real Madrid and Chelsea, it will be game, set and match to City.