HE was supposed to be Ed Boy — but Woodward is now the one who is being closely monitored at Manchester United.
Executive vice-chairman Woodward — one of the most powerful figures in world football — should command instant respect.
But Woodward is feeling the heat, with owners the Glazers scrutinising his performance after their failure to qualify for the Champions League.
United are outsiders again, failing to make Europe’s elite club competition and finishing a staggering 32 points behind champions Manchester City.
Woodward, already on his fourth managerial appointment, is on trial. He needs a good summer.
United’s haphazard approach to transfers, with Woodward squandering fortunes on a squad of under-achievers, has put him under pressure.
He is a public figure — but his football acumen is being privately questioned by United’s demanding American owners.
Woodward loves the limelight, the notoriety that comes along with being able to hire and fire some of the biggest names in world football.
There is also a responsibility to match the expectations of United supporters after years of sustained success under the power axis of Sir Alex Ferguson and David Gill.
Woodward has come up short. He has had enough time to learn the ropes, to become adept at spotting and negotiating with top-class footballers.
It is not his bag. Woodward has failed to modernise United after ticking off another year without winning the Premier League title.
They have not been kings of England since Fergie retired from management in 2012-13.
With a squad of over-paid players, they are not equipped to challenge bitter rivals City and Liverpool. And history will not reflect well on Woodward.
The bottom line is that these guys are money men, with the Glazers patting Woodward on the head when revenues reached a record £590million.
He trousered £4m last season, a 60 per cent pay hike after United returned to the top of football’s annual rich list compiled by Forbes.
But big bucks demand big results on the pitch. He has fired three managers, with hefty compensation packages racking up for David Moyes, Louis van Gaal and Jose Mourinho.
Now Woodward cannot afford another failure against his name.
It was his decision, after being turned down yet again by Tottenham manager Mauricio Pochettino, to give Ole Gunnar Solskjaer the gig full-time.
But Woodward and Solskjaer are making a hash of it.
United finished sixth in the Premier League after their form tailed off in the final stretch of the season.
Beyond that, Woodward’s appalling record in the transfer market is amplified because of United’s worldwide profile and the headline-grabbing figures.
There is no hiding place for a man who spent £89m bringing Paul Pogba back from Juventus in 2016.
Romelu Lukaku, a £75m buy from Everton, can leave after scoring just 12 times in the Premier League this season.
Then there is the boardroom uproar over Alexis Sanchez, the £505,000-a-week misfit signed from Arsenal in January 2018.
The club are still coming to terms with the end of the Mourinho era — the reasons why it went so wrong, so quickly.
The Special One timed his run yesterday, with a reminder that he wanted modern methods implemented at their Carrington training centre.
During his stay in Manchester, he frequently compared Real Madrid’s razor-sharp approach with United’s tired, out-dated model.
This club has been unloved for years, getting by on reputation and their astronomical annual income to bring in the best players. But that will be tested this summer.
No matter how big the pull of wearing the United jersey, it does not mean as much when they cannot offer Champions League football.
Elite footballers wants to be playing Juventus, Real Madrid, Barcelona and Paris Saint-Germain under the floodlights.
United are another year away from that — at least.
Woodward faces a different type of test, with the challenge to bring in players earmarked with big potential.
There will now be even bigger reliance on the club’s scouting and recruitment department — with its archaic structure another Mourinho grievance.
Woodward will need to back Solskjaer’s judgment, the manager he hired on a three-year contract in March after he bounced into the job in December with some impressive post-Mourinho results.
Together, they will have to sift through a lengthy list of targets — working out whether the likes of Bruno Fernandes, Gelson Fernandes and Idrissa Gueye are really Manchester United material.
Those are the sort of names in circulation, the type of players United are being linked with after failing to make top four.
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The best now all have their sights set elsewhere, with the glamour and appeal of the Champions League holding so much sway.
It is Solskjaer’s job to get them back there, to find a way to restore United to the top of English football.
And if that fails, they will have to knock it on the Ed.