Now he is free of the stresses of running Manchester United, Ed Woodward half-jokes he wishes he had replaced David Gill a year later.
Woodward was confirmed as their inaugural executive vice-chairman in February 2013, effective from July 1. By that time, Sir Alex Ferguson had moved upstairs and another Scot was in the manager's office at Carrington.
Woodward joined United in 2005 and was still cooing about the 3-1 rout of Arsenal in the 2009 Champions League semi-final ten years later. Like just about everyone at United, Woodward was in awe of Ferguson's Pied Piper presence and was 'absolutely devastated' that he retired.
A staff member likened United to the opening sequence of Saving Private Ryan and being peppered with machine gun fire. Open season has been declared on United almost monthly during Woodward's time and he has often stared at both barrels.
From the outside, Woodward could appear more preoccupied with commercial matters when those close to him maintain he only cared about them as it enabled United to compete in the transfer market, as they were not a state-owned club or bankrolled by an oligarch.
Woodward regrets his infamous quote, 'Playing performance doesn't really have a meaningful impact on what we can do on the commercial side of the business' during the recorded May 2018 investors' call. The incumbent United director of communications, Charlie Brooks, changed the script so that Richard Arnold, rather than Woodward, would comment on commercial matters during the calls.
Moyes, Louis van Gaal and Jose Mourinho all developed an unflattering opinion of Woodward during their time working under him and Woodward regrets becoming embedded in football-related decisions. His first summer transfer window in 2013 ended in farce as United only signed Marouane Fellaini, having unsuccessfully bid for Ander Herrera, Sami Khedira and Daniele de Rossi, while a loan move for Fabio Coentrao collapsed.
The defunct fanzine RedIssue dubbed Woodward an 'imposter' on his first deadline day in 2013, the word used deliberately after 'imposter' lawyers, claiming they were acting on United's behalf, attempted to finalise the transfer of Herrera.
Woodward personally flew to Barcelona to gauge the possibility of signing Neymar in 2015 and is believed to have approved of a piece by a former journalist at the Manchester Evening News that billed him as the club's de facto director of football. Woodward maintains football decisions were made by football people and sardonically suggested he should have hired Gary Neville at the start.
Woodward likens running United to having an albatross tied around one's neck, weighed down by the history and standards set by Ferguson and Sir Matt Busby. Woodward longed for the albatross to 'start flapping its wings' so United could do amazing things.
United won three trophies during Woodward's eight-and-a-half-year tenure. Some United fans arranged for a banner to fly over Turf Moor reading 'Ed Woodward specialist in failure' in September 2018. Woodward accepts his time as executive vice-chairman was a failure.
The main successes identified by Woodward were off the pitch; keeping ticket prices frozen and the club's commendable conduct during the first lockdown in 2020 when they refused to furlough staff and donated millions to the local community. Woodward was a more communicative figurehead than the aloof Gill.
On the pitch, a myriad of mistakes were made. Moyes inherited a structure deemed 'unfair' and when the rebuild process belatedly began in 2014 United granted Van Gaal too much autonomy and they were 'anchored' by his unsuitable signings. United spent over £200m on 11 players under Van Gaal and Marcel Bout, who assisted the Dutchman in recruitment, ironically remains the club's head of global scouting.
Recruitment defined Woodward's legacy and there is an acknowledgement United got more wrong than right with players and managers. There is frustration that United rose to second in the second full seasons of Mourinho's and Ole Gunnar Solskjaer's reigns before both were dismissed midway through the third.
Jurgen Klopp, Thomas Tuchel, Mauricio Pochettino and Antonio Conte were all out of work at one time or another while Woodward ran United and he rues missing the boat with certain coaches. Although he is hesitant about naming names, sources say he consistently speaks glowingly about Klopp and Pep Guardiola. Conte was never a candidate to succeed Solskjaer and an informal approach was made to Pochettino last year.
Woodward is believed to have given up on presenting the derided 'cultural reset' as a success. He will attend football board meetings until the end of June but will have no input on the decision to appoint United's next permanent manager. United are already maximising interim manager Ralf Rangnick's consultancy expertise.
Woodward is grateful for the support of matchgoers during a turbulent time and was particularly praiseworthy of the thousands who continued to support United as they were thrashed 5-0 by Liverpool at Old Trafford in October. Addressing United's social media fanbase has been more 'challenging'.
The football structure, seemingly finalised with the appointments of John Murtough and Darren Fletcher as football director and technical director in March, is actually incomplete and club sources say 'there is another 10 per cent to finish'.
United are 22 points adrift of Manchester City - the exact same distance at the end of the chastening Moyes campaign - but there is belief at the club the average age of the squad and quality is the best in some time.
Some sliding doors moments rankle for Woodward beyond Ferguson's retirement, such as Luke Shaw's double-leg break in Eindhoven in September 2015 and Paul Pogba's hamstring strain at the start of the 2017-18 season. United level on points and had scored as many goals as City after seven games in 2017-18 but, over the next four fixtures without Pogba, they won one, drew one and lost two. City won all four to go a decisive eight points clear in their centurion season.
The issue went beyond Pogba's absence. A portion of his rehabilitation was done abroad and the breakdown in communication with Jose Mourinho signalled the beginning of the end of their working relationship, which became so toxic Pogba revelled in Mourinho's sacking on Twitter.
Woodward's successor, Richard Arnold, has developed a thick skin in his role as managing director and was identified as the obvious replacement to become chief executive. Arnold was brought to United by Woodward, whom he met at the University of Bristol in the early 90s, in 2007 and although his investment banking background has been described as an unideal starting point he is described as a 'motivator'.
The considerable commercial growth of United under Woodward would be attractive for other clubs and it is understood he is eager to stay in the football industry.
