Ed Woodward's time at the helm of Manchester United is destined to go down as a failure.

Woodward knows huge mistakes were made, some more obvious than others.

Making it known to the media, in the very first week of his very first pre-season tour, that he was heading home on "urgent transfer business" that never actually materialised was a major own goal.

Yet the faults went much deeper.

Looking back, United should have been making plans for Sir Alex Ferguson's succession before the Scot left in 2013. Woodward didn't know at the time - but does now - that asking David Moyes merely to step into his fellow Scot's shoes was presenting him with an impossible task.

Ferguson ran United to his own specifications. His authority was unchallenged. When Moyes came in, the structures needed to operate a club of United's size did not exist.

David Moyes was billed as "the Chosen One" as he had Sir Alex Ferguson's backing, but his reign lasted just 10 months

So began a downward spiral which senior figures at the club are adamant has been halted but others feel continues, particularly when compared to the progress made at Manchester City during the same period.

"This has been City's era. Nobody could say otherwise," says one club source.

The poor results brought huge criticism. And numerous concerns for the safety of Woodward's family, some reported, many others not.

Yet BBC Sport understands he has no regrets, beyond wishing he had the chance to work more closely with Ferguson at the start.

Living with the past

United remain England's most successful club, with 20 league titles, 13 from the Ferguson era.

But it is felt by some at Old Trafford this has the potential to be a negative as well as a positive.

Woodward and successor Richard Arnold have used the club's vast following on various social media platforms as a positive during talks with investors.

Yet it means debate around the club's fortunes is enormous and long-lasting. Current issues behind the scenes involving disenchanted players, some of whom would like to leave during the current transfer window, are being played out in public, which creates uncertainty inside the club.

Sources say Woodward has tried to address that, but it is not easy, especially when, commercially, the club needs to exploit all avenues.

Richard Arnold will replace Woodward as United's most senior executive on 1 February

Woodward will leave Old Trafford with the reputation of someone who was good at maximising United's brand but poor at running the football side, to the extent it has been said he wasn't that bothered about it.

He has repeatedly - and forcefully - rejected those suggestions. He is adamant the commercial side exists to fund football ambitions in an era during which the club are trying to compete with domestic rivals of which, as people at United point out, two are state-funded and another by an oligarch.

Put the counter argument to them that the club would be in a healthier state were it not for the £844m the respected football finance blogger Swiss Ramble

said in September 2021 they had spent on various financing costs over the previous 11 years, and the answer returns that they have the money to compete with City and Chelsea, and now the key is better recruitment.

It is accepted the current squad needs strengthening, particularly in central midfield. Crucially, the club are also desperate to get their next managerial appointment right. For all the negativity around interim boss Ralf Rangnick, United believe he has the credentials to make sure the club's next appointment is the correct one.

The future

It is understood Woodward is yet to decide his future path, that he will take some time out until the summer before considering his options.

It was the advent of European Super League that triggered his United resignation - he had been involved in numerous meetings over the previous two years but felt, as had always happened before, they would end up being used to pressurise Uefa into more concessions for the bigger clubs, was shocked when that turned out not to be the case and didn't agree with the proposals put forward. And he has a coherent stance on the current state of the game.

Along with senior figures at many of Europe's leading clubs, Woodward believes Fifa and Uefa have increasingly attempted to turn themselves into media companies, doing deals he does not feel they, as the regulator, should have any involvement in.

It will be interesting, given Woodward's experience, his previous senior role at the European Clubs' Association and his stated enjoyment of the football world that could easily have scarred him, whether another club, or overarching body, see the benefit of using his wisdom.

In an open letter to Arnold, fans' group MUST set out a three-point plan: to tackle the decline on the playing side; rebuild trust with fans; put in place a clear and well-funded plan to improve Old Trafford

The positives don't outweigh the negative

It is easy to think Woodward's entire time at United has been a disaster.

That would be unfair.

The club have not put any staff on furlough during the Covid-19 pandemic, kept paying people who worked for the club on a casual basis and sanctioned the repurpose of kitchens to provide meals for NHS staff. Money has been ploughed into community schemes and on-pitch signings of Jadon Sancho, Raphael Varane and Cristiano Ronaldo are not the work of a badly run organisation.

Belatedly, the club launched a women's team, which is now one of the most high-profile in Super League.

There has even been some thawing of relations with supporters, some of whom were so annoyed at the club's behaviour over the European Super League they forced a Premier League match against Liverpool last May to be postponed.

Yet community work, a fans' share scheme and some much-needed improvements at Old Trafford do not balance out what has gone wrong with the first team.

And as he prepares to leave United at the start of next month, Woodward knows it.