When the elevator doors slide open on the third floor of Manchester United's offices in London's exclusive Mayfair district, you're immediately greeted by full-size replicas of the Premier League and Champions League trophies. For the past eight-and-a-half years, Ed Woodward has had to walk past them, tormented by their presence, every time he has arrived for work as United's executive vice-chairman, the man who has held the responsibility of running the club for almost a decade.

The trophies are a constant reminder of what United strive to win, but have singularly failed to throughout Woodward's tenure in charge. When Woodward, 50, clears his desk ahead of his departure later this month, the good news is that he won't have to endure the torture of walking past those trophies ever again.

The bad news? Well, there's plenty. Although Woodward is one of the most affable executives in football, a man who unquestionably feels the pain of not being able to deliver success at Old Trafford, his time in charge has been a story of underachievement on the pitch, a succession of sacked managers and far too many expensive mistakes in the transfer market. All as traditional rivals Liverpool and Manchester City enjoy ongoing success.

Woodward has long been a lightning rod for United fans' frustrations, and he has borne the brunt of much of the criticism from outside the club for failing to keep the trophy room as stacked as it had been for years prior to his appointment in July 2013. At that time, United didn't need reminding of former glory. Under manager Sir Alex Ferguson, and Woodward's predecessor, David Gill, the club had become the definition of sustained success, winning 13 Premier League titles and two Champions Leagues in 20 years.

United set the standards for the rest to follow, and when Ferguson and Gill stepped down at the end of the 2012-13 season, the club's owners, the Glazer family, promoted Woodward from his role in charge of United's supremely successful commercial department to run the club on a day-to-day basis and ensure that the trophies kept on coming. Woodward had earned the right be to the top man at Old Trafford, having made United the most powerful money-making machine in the game, but he has learned that selling shirt space to sponsors and negotiating for the world's best players and managers are two wholly different responsibilities.

But as Woodward prepares to walk away, having announced his intention to quit last April following the controversy around United's involvement in the failed attempt to launch a European Super League (ESL), he will admit to friends that for all the modernisation and commercial revenue off the pitch, his time in charge has been a failure. United haven't won either of those two trophies that he sees every day, and for all the players he has signed for United -- including Paul Pogba, Zlatan Ibrahimovic and Cristiano Ronaldo -- nobody generates quite so much divisive opinion and condemnation as Woodward.

Is that fair? Is Woodward misunderstood and misrepresented? The truth can often be found many layers beneath the surface, but first impressions tend to last and, for all of the forward-facing work he has overseen -- rebuilding United's internal structure, the recruitment network, investment in the youth academy -- and refusal to increase season-ticket prices throughout his time in charge, the story of his time as Old Trafford's senior executive has always been viewed through the prism of the mistakes made right at the outset.

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A 'horrific' start to the job

It was in the Park Hyatt, Sydney, located just beneath the city's iconic Harbour Bridge, in July 2013 that the wheels began to fall off for Woodward and Manchester United. Having been in charge of the club for less than a month, it was clear he had been handed a bigger challenge than he could ever have imagined.

Sources have told ESPN that Woodward believes that the mistakes made in that first summer following Ferguson's retirement impacted the club's psyche and continue to haunt United today, and that David Moyes, appointed as Ferguson's successor prior to Woodward's elevation to executive vice-chairman, was given a job he could never succeed in because the club was simply not prepared for life after Ferguson.

Ferguson had left behind a winning machine on the pitch, but a club without a modern structure off it. In terms of scouting intelligence, sources said that Ferguson leaving was like owning a vault of treasure, but losing the key.

Woodward wanted to launch the new era with a box-office signing to help make up for the loss of Ferguson's presence and aura, but the caution of Moyes, who vetoed a deal for Barcelona's Thiago Alcantara, combined with Woodward's transfer market naivety left United humiliated by a succession of failures. Ronaldo, Gareth Bale, Cesc Fabregas, Daniele De Rossi were all targeted and gave United encouragement.

In an effort to land a big signing, Woodward left Australia to fly back to Manchester, citing "urgent transfer business," but nothing happened. The weeks dragged on, agents played United and Woodward against other clubs and, having targeted a superstar, the only deal that came off was the £27.5 million signing of Marouane Fellaini from Everton, three minutes before the 11 p.m. deadline on transfer deadline day.

Woodward and Moyes had contrived to make a huge mess of their first transfer window, and Woodward's reputation arguably never recovered. Despite subsequently completing deals for the likes of Pogba and Ronaldo, Woodward has been unable to shake off the reputation of being a man who can't strike a deal without unnecessary drama.

He has since told friends that Ferguson's departure gave him a "horrific" start to his job, denying him the chance to work with a "genius" and be guided by his experience and knowledge. Ferguson told Woodward of his plan to retire within seconds of sitting down at a lunch arranged by Woodward to get to know the man he expected to work alongside. Not being able to work with Ferguson is Woodward's biggest regret.

Woodward also now concedes he made recruitment mistakes for the first three years of his time in charge and accepts that an initial belief that United's wealth and financial power would enable them to take a shortcut back to the top was misguided. He told reporters in 2014 that United were simply too powerful commercially to suffer more than a one-season blip, but time has proved otherwise.

There is also an acceptance that the club further lost its way under Louis van Gaal, Moyes' successor, because the former Ajax and Barcelona coach was given too much control over player ins and outs.

"Only now are we able to look at signings and say that we have made them better and could move them on for a profit," a United source told ESPN in relation to the club's transfer strategy in recent years.

It has taken some tough lessons to get to the point where United now believe they are able to recruit players as stealthily and successfully as City and Liverpool. Those lessons include telling Jose Mourinho that, after Bastian Schweinsteiger's disastrous and injury-affected move from Bayern Munich in 2015, they would not make a similar mistake by signing defender Jerome Boateng from the German club three years later.

And when dealing with Real Madrid, as they did when a 13-hour overnight summit between club president Florentino Perez and Sergio Ramos saw the defender abandon talks over a £35m move to Old Trafford in 2015, United and Woodward have learned to be wary of attempting to do business with their fellow super-clubs.

The United recruitment team now looks for the next big thing, winning the race to sign Atalanta's Amad Diallo in 2020, but failing to persuade Jude Bellingham to reject Borussia Dortmund in favour of United when leaving Birmingham in the same year.

There was also a narrow failure to sign Erling Haaland in 2020, when the striker also chose Dortmund over United when leaving FC Salzburg. United remain interested in the Norway international, but they are in a congested field and the managerial uncertainty at Old Trafford is unlikely to help.

The struggle to create Man United's new identity

Woodward has fired four managers in eight years, and it is not a record he is proud of.

"Ed really wanted a manager for six or seven years, like Pep Guardiola at City or Jurgen Klopp at Liverpool," a United source told ESPN. "There have been some real sliding doors moments with some of the best coaches in the game, but the dots never joined up when they needed them to."

Moyes was sacked after less than a season in charge, and Woodward has made it clear to the now-West Ham manager that he feels United let him down during his brief spell in charge. A rookie chief executive, a group of players ill-equipped to move on after Ferguson and a club searching for a new identity all conspired to make it an impossible job for the former Everton boss.

In 2014, Woodward consulted Ferguson, Gill, Sir Bobby Charlton and former United captain Bryan Robson to map out the requirements for the next manager. Sources have said United needed to "change the engine while flying," so they turned to the experience of Van Gaal after failing to tempt Klopp and Atletico Madrid's Diego Simeone to follow Moyes. Woodward had set "exciting, attacking football" as a key pillar for all potential managers, but Van Gaal delivered anything but and, two years later, was dismissed the day after winning the FA Cup because the sterile football had alienated the players, who made it clear to Woodward that the Dutchman had lost the dressing room.

After City beat United to signing Guardiola in February 2016, United turned to Mourinho -- a polarizing figure known for winning, but winning ugly -- in an attempt to take another shortcut to success. Sources told ESPN that Woodward read eight books on Mourinho before hiring the former Chelsea and Real Madrid coach. "Ed knew what United were getting," the source said. "He knew it would become toxic and end badly, but the gamble was that he would win the title before it all went sour. That obviously didn't happen."

With Moyes, Van Gaal and Mourinho, when the end came, it had been signposted for weeks, even months, that the appointment wasn't working, yet all remained in post until a bad situation had become irretrievable.

History tends to repeat itself at United, however, and Woodward found himself in that position again with Ole Gunnar Solskjaer earlier this season. Solskjaer, a United legend who scored the winning goal in the 1999 Champions League final, oversaw a 5-0 home defeat against Liverpool followed by a 2-0 loss to City this season. He had failed to win a trophy during his almost three years in charge and the lack of any kind of stylistic improvement in the team appeared to make his exit inevitable.

But Woodward refused to dismiss Solskjaer until he simply had to. Why? Because, sources say, Woodward believe Solskjaer was "a good man who gave it everything."

United resisted the opportunity to tempt Mauricio Pochettino from Tottenham in 2019 because Solskjaer had done so well as interim manager following Mourinho's sacking in December 2018. They also chose not to remove Solskjaer for Pochettino when he left Spurs in November 2020, or push for another top manager, Thomas Tuchel, when he was sacked by Paris Saint-Germain a month later. (Tuchel has since taken Chelsea to a Champions League title.)

"Ole had us near the top of the table when Pochettino and Tuchel were available," a United source told ESPN. "So the club couldn't sack him in that situation. It was like God was trying to f--- us over."

When United finally dismissed Solskjaer, one coach with a winning track record -- Antonio Conte -- was available and keen to take the job, but sources said that Woodward and his fellow executives regarded the former Chelsea and Inter Milan coach, now at Tottenham, as being too demanding for the squad he would inherit at Old Trafford.

When United hire a permanent successor to Solskjaer this summer -- Ralf Rangnick has taken interim charge for the rest of this season -- Woodward will play no part in the process. Richard Arnold, his successor, and the Glazers will make the final decision and sources have said Pochettino will once again be prominent in their discussions.

Another summer brings another crucial appointment, and one United can't afford to get wrong. But that's not the first time you've heard that message coming out of Old Trafford.

Where will United go from here?

Woodward will make a clean break from United when he leaves his post. Despite reports of him being given a lucrative consultancy role by the Glazers, sources say that he will take time off before considering his next steps,

Woodward and his wife, Isabelle, have invested in the Quinta Da Pedra Alta winery in Portugal's Douro Valley, but the former investment banker retains a hunger to work again in football. Sources have told ESPN that he resigned at United as a point of principle after being unable to support the ESL breakaway plans.

"He has friends who support West Ham and Leicester and he just couldn't throw his weight behind a competition that had no relegation and would leave clubs like that with no hope of ever competing at the top again," a source said.

Despite the perception outside of Old Trafford that Woodward has failed during his time in charge of United, his loss is keenly felt by the Glazers, who regard him as having driven the club's commercial growth after initially advising them on their 2005 takeover while working for JP Morgan.

"If the Glazers had 800 staff and they had to make 799 redundant, Ed would be the last man standing," a source told ESPN. "Joel Glazer trusts Ed implicitly, so behind the scenes at least, this is a big moment for the owners."

Woodward's replacement, Arnold, has followed the same career path as the man heading out of the door, going from Bristol University to the banking sector and then to Manchester United. To many he is regarded as nothing more than a Woodward clone, another Glazer executive who ultimately only acts as the gatekeeper to those who make all the big decisions: the Glazers. Yet sources also told ESPN that Arnold is a more demanding, forceful figure than Woodward, "somebody who will carry the flag and lead," so there may be a subtle change in approach to the way the club is run and how managers and players are recruited.

Arnold's connection with Woodward ensures that the new man will have to emerge from his predecessor's shadow and assert his own personality, however.

Woodward has been criticised -- criticism he accepts as valid -- for being too accessible in his early days; Arnold is less likely to be encouraging supporters and the media to offer their opinions. Arnold is personable, but while Woodward is the type of character to invite you into a room, Arnold is more likely to usher you out of it. And the big office at United, the one past the Premier League and Champions League trophies, will soon be his.

Right now, on Woodward's desk, there sits a framed photograph of the scoreboard at Olympiakos in February 2013 which reads "Olympiakos 2 Manchester United 0." It was taken by Woodward as Moyes' United trailed in their Champions League round of 16 tie against the Greek champions; the idea was that it would provide a constant reminder of the lowest point of his time in charge. Things arguably got worse, but it's a reminder nevertheless.

Arnold won't be able to get rid of those two trophies, but he can start by removing the photograph and hoping it can be replaced with something more uplifting in the years ahead.