Credit: Rory Martin for Bleacher Report

On October 20, 2014, just for half a moment, Ed Woodward’s poker face slipped on a freezing-cold night at the Hawthorns, home of West Bromwich Albion.

To Woodward's right sat Sir Bobby Charlton—a reminder (if one was needed) of the glories that his employers, Manchester United, had tasked him with renewing when they elevated him to the role of executive vice-chairman 18 months earlier.

On the pitch in front of him was a further nod to the very scale of the ambitions he’d been charged with satisfying: marquee signings Juan Mata, Radamel Falcao and Angel Di Maria—their mammoth transfer fees still a fraction of the total value of the team in red.

Away to Woodward's right at the Smethwick End were 3,000 impatient Manchester United fans and, nearby, the reason for their ire: the blaring neon scoreboard silently confirming that the team into which he had poured so much of the club’s money were trailing 2-1 to West Brom, a middling Premier League club lurching through their own tumultuous season.

Woodward didn't expect the TV cameras to be fixed on his expression when his frustrations boiled over in the 77th minute, although the man tasked with overseeing the world’s most adored football club might have known better than to assume scrutiny over his every move would ever dissipate for more than a moment. Indy Football provided highlights regarding Woodward's questionable expressions:

With Woodward's lips being broadcast live to an audience of millions, he muttered something in testament to his disgust at his team’s struggles and was subsequently crucified by a baying press.

If the man calling the shots thought United were a shambles, then by what measure could this be said to be a club in control of its destiny?

The sequence of events that placed Edward Gareth Woodward—physics graduate, accountant and seven-year veteran of Manchester United's relentless commercial operation—in effective charge of the world's best supported football club two-and-a-half years ago has indefinite origins, but a challenge to the club's ownership model back in 2003 laid much of the groundwork.

It began with discussions between (what was then called) Shareholders United and the United board to form a trust that could buy shares in the club that would be held in perpetuity. The hope was that this might create a dam in the ownership model that would have made a full takeover, be it domestically or from overseas, impossible.

There was enthusiasm for the idea from within the boardroom, but the deal never came to fruition.

Duncan Drasdo, chief executive of (what is now called) Manchester United Supporters' Trust, said this was largely due to resistance from Shareholders United, which feared the new arrangement might be used by the board to further its own interests. So when Malcolm Glazer and his family, owners of the Tampa Bay Buccaneers, made their move in 2005, the club were sitting ducks.

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"By 2005 there wasn't any really coherent counter-offer," Drasdo said. "We'd had various approaches from representatives of Qataris and so on, but nobody came forward with a plan that would have been anything other than another takeover by another group that would have excluded the supporters."

The corporate minutiae that forced through the 2005 takeover was complex and delicate, and it demanded a dexterous financial wit to wrangle into being. Woodward, assigned by investment bank J.P. Morgan to provide that accounting agility, won the minds and the hearts of the Glazers with his work to resuscitate a failing deal at the 11th hour. Without this thought in place, it is impossible to make sense of the last decade at Old Trafford.

The Glazers' takeover deal was last-minute and desperate in terms of interest levels and the loans necessary to pull it off—one condition was that the new owners' shares in the club could have been repossessed had they failed to keep up repayments—and Woodward's work in structuring the deal to pull the Glazers out of a hole was the foundation of the esteem in which his employers held him.

"You're going to be pretty grateful to the man who's got you out of that one, aren't you?" Drasdo said through a dry smile.

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Woodward's rise to the top was more carefully managed than it looked from the outside. In the years leading up to David Gill's departure, a carefully choreographed process of change was engineered at Old Trafford, with Woodward effectively becoming the chief executive's shadow.

The Glazers' Chosen One was in daily contact with his employers in the U.S.—Gill's communications were reduced to barely once a week—and Woodward became the go-to man for running the company.

Gill ran the football club, presiding over correspondence with the Football Association and the Premier League and conducting transfer business, while Woodward took care of Manchester United the business as executive vice-chairman, the role for which he had been groomed from the start. It is a role he has been thrust ever deeper into since taking the top job.

"Selling the diamonds" is how Woodward likes to characterise the work he does for Manchester United's brand globally. The commercial operations at the world's biggest clubs, including Barcelona and Real Madrid, look to Woodward's United as a trailblazer for how to turn enthusiasm abroad into revenue.

Before Woodward, nobody was doing this. Not in England, Spain—nowhere. Selling sponsorships in this way has moved the goalposts, not just at United but also across commercial departments everywhere.

For years, United's vast popularity in places like India was a wasted resource. Fan numbers that ran into the millions weren't converted into revenue because the brand as it was being used was too easy to counterfeit.

One club insider, who asked to remain anonymous and was close to the internal workings of the succession, told Bleacher Report: "Ed rose to the top job because he was adding to the bottom line. That's where the power base lies now because he was the one who has changed things to bring the money in. That's been his reward.

"The power base now at Old Trafford lies with Ed and Richard Arnold (group managing director and director of Manchester United PLC). They're bringing the money in, so they're making the decisions. It's them and nobody else."

This monetisation of a vast supporter base abroad has been little short of revolutionary.

"The club really struggled for a long time overseas," the club insider continued. "They had such a vast supporter base, but they didn't make a cent from it. They tried to launch a magazine, and it was counterfeited. All the shirts they were selling in places like Thailand and Malaysia were counterfeit, and what Ed did was splice their fanbase into geographic regions and sell partnerships to commercial sponsors.

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"So he started going to companies and saying, 'You can use our logo on your bottle of vodka, you can use our players to promote your product.' It sounds straightforward, but absolutely no one was doing it. And suddenly he was bringing in so much money to the club that the Glazers felt there was little option but to turn to him for the top job."

Former United commercial consultant David Chattaway described Woodward's operation as "like filling up the boxes on a huge matrix," as a team of operators that proactively and relentlessly seeks opportunities around the world. "It's almost become an industry joke about United—a deal a day," Chattaway said. "Real Madrid and Barcelona are chasing Woodward's model at the moment, thinking that's where the money is."

Between 2009 and 2014, the portion of United's revenue generated from commercial activities grew from 23 per cent to 43 per cent (via Chelsea Dulaney of the Wall Street Journal).

The work Woodward began from United's Mayfair office as head of the commercial operation has continued since 2013; the club is tied into deals that have created official wine partners and tyre partners as far away as Chile. FLOW Jamaica confirmed its Caribbean partnership with Man United:

Former players have signed up as ambassadors to promote sponsors' brands abroad. If Wayne Rooney can't fly overseas to promote United-aligned products, then why not send Andy Cole, as Woodward duly did when the former striker pitched up in Qatar in September 2013 on official United commercial business.

Woodward still speaks with Sir Alex Ferguson regularly, as he does with Gill and Sir Bobby Charlton, giving the new man a direct line to the whys and wherefores of how the club functions close to the bone. Drasdo's fears that the succession was poorly handled are unfounded, and Woodward still enjoys a wealth of firsthand support from people who know the club inside and out.

But Woodward's real achievement has been harvesting the great knowledge of his forebears while forging a new club identity that is relevant to the 21st century. It seems absurd to think now that United didn't establish an official Twitter account until 2013; that was Woodward's call, and within days he was using it to project a new kind of club to the world.

United's 2013 preseason tour of Asia had been rocked by an injury to Rooney, which forced the striker to return to Manchester and jeopardised his chances of playing any further part in the club's summer schedule. Meanwhile, reports persisted that the England man was on the verge of signing for Jose Mourinho's new-look Chelsea, as noted by the BBC's Ben Smith, as his relationship with the club continued to lurch awkwardly.

When Rooney recovered in time to face AIK of Stockholm (as noted in the aforementioned Man United tweet) just a week-and-a-half before the start of the new Premier League season, Woodward authorised a release via the club's Twitter feed. It was almost cinematic in its bombastic gloss, placing the club's talisman publicly at the heart of brand United. "Back!" it chimed in thundering surround sound.

The move was as anti-Ferguson as any United fan could have imagined, and it marked the rebranding of the club under its new leader.

On Manchester United's team flight back from Moscow in October, part of a gruelling 3,000-mile round trip and after a hard-fought Champions League draw with CSKA, Woodward was a conspicuous presence, making the rounds among players, staff and journalists in what was part of a concerted and fruitful effort to knit the overlapping layers of the club together as seamlessly as possible.

If there is a consistent presence pervading this proud institution and seeking to haul it as one to its next destination, wherever that may be, it is Woodward.

The holistic approach is one borrowed from the blue half of Manchester, but it's one that forms the bedrock of United's new approach. One Old Trafford insider described the atmosphere as "far more relaxed and a much happier place to be now."

"Certainly before now there was a bit of...a reluctance to do anything that could conceivably upset Ferguson or Gill, which didn't make for the best environment. But Ed enjoys his job; that's clear for everyone at the club to see. His attitude rubs off on people around the club and has completely changed the place. Everyone is happy."

Everywhere you put the question, the answers are the same: Woodward is a charismatic and genuine man who, for all his achievements and accolades, recognises how far a smile can go in the pooling of key relationships.

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Not that placating every ego within a behemoth like United is a necessary skill—or even an obtainable one.

Rio Ferdinand made no secret of his distaste for the way he learned from Woodward in the St Mary's dressing room after a game at Southampton in May 2014 that his contract was not to be renewed.

Patrice Evra was also critical, though less publicly and only within closed circles, of the new United chief's handling of his Old Trafford departure in July 2014. Robin van Persie, conversely, was full of praise for the man as he departed for Fenerbahce in July.

Woodward has learned quickly that a one-size-fits-all approach is unsuitable for taming the modern footballer. But we should remember he was not bred as a football man. When Ferguson announced to the incoming chief executive in the spring of 2013 that he was to be stepping down, Woodward was devastated—his water wings slashed before he'd even dipped his toes in the ocean. This, though, turned into the club's advantage.

Woodward brought to his role a broad and rich understanding of the world beyond Manchester United. This in turn has informed his approach to management.

In 2013, shortly after taking the top job, he said this in reference to J.P. Morgan's takeover of his firm, which had cost the jobs of a number of his colleagues: "You don't whinge at losing your job at an investment bank when you've been given a chance to work for one."

Translation: This is the world in which we live; deal with it. It's a philosophy Woodward has been forced to stand by as he's moved headlong into the lonely world of the football transfer market.

In that world, perhaps more than any other area of his work at United, perceptions of Woodward slam up against the reality of what has been a crash course in negotiating deals for the globe's biggest players—and their egos.

Much has hinged on how well Woodward has absorbed the transfer-market nuances—learning how this particular game is played and how quickly things move.

United's chief exec has been quick to cultivate a relationship with Jorge Mendes, who represents some of the game's biggest names, including David De Gea, Radamel Falcao and Angel Di Maria—three stars with their own part to play in the Story So Far for Woodward. Mendes also looks after Cristiano Ronaldo, of course—a name constantly linked to a United return in the gossip columns, such as the Sunday Mirror's (h/t the BBC).

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Contacts are the lifeblood of any high-powered industry, football and corporate banking included, and the courting of Mendes has paid conspicuous dividends. De Gea, Falcao and Di Maria were, to some extent, persuaded that United was the right club for them.

Details, such as the decision to afford Mendes' daughter a work-experience role at Old Trafford, go a long way where cultivating closeness and trust are concerned, and the inside line is that neither Falcao nor Di Maria would have been likely to join the club had Woodward not handled the relationship with Mendes as delicately as he had.

"Trust" is the golden word. Andy Mitten, editor-in-chief of fanzine United We Stand, has followed the international transfer market from the inside out for over a decade and is intimately acquainted with how United's top man has enmeshed himself within a sometimes murky environment.

"There needs to be that level of trust, just like in any business deal," Mitten told Bleacher Report. "The relationship Ed has cultivated with Mendes and with others has been hugely advantageous, and we've seen that in some of the deals that have been made for Di Maria, Falcao and so on.

"He's really learnt to decipher who is who. There will always be agents trying to insert themselves into a deal where a club like United is concerned, but it's about knowing who represents the player you're after and how to cultivate a relationship with them. Ed is really getting to know who represents whom. Just as importantly, he's getting to know whom he can trust. It all comes back to trust in this business."

In January 2014, United had reached the nadir of a wretched season. Beaten six times at Old Trafford already that campaign, they had been knocked out of the FA Cup by Swansea City and sat a lonely seventh in the Premier League.

Then, just when it couldn't have mattered more, two key relationships began to bear fruit for Woodward. One was the one he had struck up with Colin Pomford, a Madrid-based solicitor who in 1999 was responsible for helping Steve McManaman become one of the world's highest-paid players when he signed for Real Madrid. The other was Juan Mata Sr., agent and father of the winger twice voted Chelsea's player of the season yet conspicuously made surplus to requirements.

Mata's £37 million deal was the first internationally acclaimed, game-changing signing for the new United regime, and it came at a moment when another high-profile failure would have been at best embarrassing and, at worst, debilitating.

Trust became the watchword again.

"Mata didn't want to be part of a deal that collapsed," Mitten said. "Likewise, Mourinho didn't want to be seen to be trying to offload a player behind his back, and United didn't want to look like they were going after players and not getting them. It had to be handled very, very carefully."

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Woodward is prone to being more loose-lipped with journalists when it comes to prospective transfer targets—which goes some way toward explaining why so many deals appear to fall through—but the Mata deal was wisely kept hushed until it was signed and sealed.

One of the key lessons Woodward learned from his time shadowing the outgoing Gill was the importance at a club like United of a tight working relationship between the chief executive and the manager, never more so than when transfer negotiations are at the sharp end.

In some ways, Woodward's United buck the trend in this respect, as football in England rolls toward the more continental model of transfer committees, directors of football and so forth that often exclude the manager from deals.

One thinks of the Andriy Shevchenko and Michael Ballack deals at Chelsea that helped spell the end of Mourinho's first reign. At Real Madrid, Carlos Queiroz went six months without a word from his president. But Woodward observed the success of Ferguson and Gill's synergy and has sought the same rapport with Louis van Gaal.

Memphis Depay, for example, was set to sign for Paris Saint-Germain in July until a well-placed phone call from Van Gaal on the eve of the deal derailed the move and turned the PSV man's head in favour of United. Woodward and his team moved in to crunch the numbers, but it was the synergy between the two men that allowed the deal to go through.

Likewise, when Anthony Martial signed for the club in September, it was Van Gaal who personally convinced Woodward that the young Frenchman was worth £36 million of the club's money. Though the executive vice-president played a part—unable to communicate directly with the young French star on account of the language barrier—he chose instead to put the newly arrived Morgan Schneiderlin on the phone to Martial to wage the battle for the Monaco man's signature, before dispatching one of his close lieutenants to Paris to shore up the deal.

"The words Ed uses are 'papering up the deal,'" Mitten said. "This idea of him flying all over Europe is wide of the mark. He cuts the numbers certainly, and he's absolutely the boss of it all. But Old Trafford enjoys a network of engineers for wrangling transfers that is largely unrivalled; players and number-crunchers alike come together to forge key deals, but [they're] always fully orchestrated by Woodward. At the sharp end of negotiations, he will be there. Ed was the one who OK'd the Martial deal. It's all his call."

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This synergy of the working relationship between chief executive, manager and staff has borne fruit in a hundred ways at Old Trafford, but it also acts as a reminder that some of the new regime's early transfer failures were as much a result of an ineffective partnership with David Moyes as they were the naiveties of a new man in a tough job.

Woodward and his team had meticulously constructed the Thiago Alcantara transfer before hesitation between Moyes and his coaching staff caused the deal to collapse. They had come to the conclusion that the Barcelona man wasn't United material.

"Woodward had worked hard on that deal," said one club insider, who asked for his identity to remain secret. "He'd done everything to get the paperwork sorted and the deal in place, but Moyes dithered and dithered and decided Thiago wasn't for him. Woodward is very good behind the scenes, but you need everything to be in place at all levels of the club for big deals to come off."

The buck may stop with the man at the top, but if every cog in the system isn't turning in sync, then whatever rhythm that exists inside the club's transfer policy is wrecked—and the blame falls at the door of the man with his finger on the button.

On March 25, 2014, Woodward sat in the directors' box at Old Trafford and watched Moyes' Manchester United lose 3-0 against Manchester City.

A toothless United managed just four shots on target, their attack was blunt and the overall performance was dull and depressing to behold.

The prospect of a humbling season away from club football's top table, the Champions League, loomed large. Fans were miserable and laid blame on two people in particular: Moyes for presiding over a woeful team and Woodward for failing to give them a product to believe in.

Football's short-termism has a way of making the dark times seem sticky and permanent. Today's mistakes will define tomorrow's opportunities and leave us in a time warp where a learning curve can seem like a catastrophic wrong turn.

The winners will be those who can keep their heads when those around them are preparing for the end of the world—those who invest in themselves the belief that things will eventually get better.

Until now Woodward has been of that category, but how he reacts to the current malaise United are suffering under Louis van Gaal will define the next chapter in a career that has known no ceiling.

Will this serial winner in football business find a way to keep climbing, or is Woodward destined to ultimately fall back down again? A big decision looms, and what happens next may define Woodward's Old Trafford legacy.

Robert O'Connor is a freelance football writer based in Sheffield who contributes to FourFourTwo, World Soccer, the Independent, Vice and others. All quotes for this piece were gathered firsthand unless otherwise stated.