Joel Glazer was desperate for Ed Woodward to stay at Manchester United despite the club's executive vice-chairman deciding that his position was untenable.
Woodward quit United on Tuesday night as owners of the six rebel Premier League clubs all saw their dreams of joining the breakaway European Super League fall flat.
United, along with Arsenal, Chelsea, Liverpool, Manchester City and Tottenham were all forced to pull out of plans to join the new league amid mounting protests from fans as well as criticism from players, managers and even government.
Woodward was one of the driving forces behind United's hopes of entering the league, and now - according to the Daily Star - he feels "huge remorse" for the part he played in discussions, admitting that it has been "one of the biggest mistakes of his professional career".
United supporters have largely celebrated Woodward's removal from the club, as he had become an unpopular figure due to a series of failed transfer negotiations and public gaffes.
But co-owner Glazer, who was lined up to become one of two vice-chairmen of the European Super League, clearly valued Woodward's presence.
He is said to have made a plea to Woodward to stop him from resigning, but the former accountant and investment banker had already made up his mind.
Speaking about Woodward's departure, Glazer said in a statement: "Ed Woodward has served the club with great distinction.
"On behalf of everyone at United, I would like to place on record our sincere thanks for his tireless work and dedication.
"His contribution to the club has been massive."
The remaining 14 Premier League clubs who did not sign up for the Super League are said to want to target executives at Woodward's level as they seek to make the rebel clubs pay for their decision.
Woodward will stay at United until the end of the season before he leaves the club.
