Ed Woodward's Manchester United job is certainly a challenging one, but for now, it is one in which he is failing.
That his predecessor David Gill left Old Trafford at the same time as Sir Alex Ferguson meant Woodward was thrust into the role of executive vice-chairman—effectively the chief executive—at the most turbulent time in the club's recent history.
His first transfer window was a disaster as he failed to get David Moyes any reinforcements other than Marouane Fellaini, a player United could have bought for less had they acted quicker, as covered by Jamie Jackson in the Irish Times.
In an interview with Matt Lawton of the Mail on Sunday, Moyes said:
It’s been well documented that we wanted [Cesc] Fabregas, [Gareth] Bale and [Cristiano] Ronaldo. There was talk of Ronaldo when I first arrived. We were close to getting a couple of major names. I’m not getting in a blame game here but things just didn’t materialise.
I had taken over from the most successful manager in history. The chief executive [Woodward] had taken over from one of the most renowned administrators in the game [David Gill]. So it was a new job for two people.
Moyes' diplomatic language aside, Woodward was the one responsible for acquiring those targets, and he failed to do so.
Juan Mata arrived in January of 2014, but the first impressive name to arrive on his watch was a transfer of convenience.
Daniel Taylor of the Guardian reported that Woodward relied on intermediaries.
Perhaps the most intriguing part of the long, complex process that finally led to a helicopter carrying Juan Mata arriving at Manchester United's training ground on Saturday is that a £37.1m deal can be arranged without as much as a telephone call between the clubs. Several months of positioning, mutual suspicion and political bargaining, and everything was done without a single word being exchanged in person.
Chelsea certainly tried. On more than one occasion, a message reached Ed Woodward, United's chief executive, that the relevant people at Stamford Bridge were open to sitting at the other side of the negotiating table. Each time, he politely declined. Everybody in football knows Chelsea want to sign Wayne Rooney and Woodward reasoned that it would be virtually impossible to keep them sweet on Mata while also informing them they could forget about anything happening the other way.
Woodward could be lauded for this approach, after all, United got their man—though at a premium price, given he was clearly no longer wanted at Chelsea—and held on to Rooney.
However, it also left the Old Trafford official open to accusations of being insufficiently experienced to handle a transfer negotiation himself.
Moyes' eventual sacking reflected poorly on Woodward. Not in as much as Sir Alex Ferguson's successor was removed—that was an entirely sensible decision.
It was the manner of the dismissal which irked. Alex Netherton of Yahoo Sports wrote that ahead of the sacking, Woodward briefed journalists “that [Moyes] was going to be sacked, forcing [him] to know he was a dead man walking and having to wait a full evening before his fate in the morning’s meeting.”
Lawton wrote of the sacking: "Ferguson told dinner guests in Manchester that week that it was 'upsetting the way it came out'. Roy Keane blamed Woodward, saying Moyes deserved more time and that the club’s executive vice chairman needed to take 'a long hard look at himself'."
Woodward's next key move was the appointment of Louis van Gaal. As things currently stand, that looks like a significant error.
Just because an appointment has not worked out, it does not necessarily make it a bad choice, though. Van Gaal had the credentials for the role, and his initial impact was positive as he guided the Red Devils back into the Champions League.
Unfortunately, this season has seen a relapse in both performances and results. A handful of impressive games have been outweighed by months of mediocrity—including seven dispiriting 0-0 draws.
Perhaps Van Gaal was not the right man for the job in the first place. Perhaps the changes in football since his peak have caught up with him. Perhaps his increasing conservatism has denied his side access to what was once best about his football—the mesmeric commitment to attack shown by his mid-1990s Ajax.
If that is the case, then Woodward deserves some opprobrium for the appointment. He could certainly have acted sooner to change things up, particularly with Jose Mourinho available.
This season's United have also been hampered by some of their failings in the 2015 summer window. In 2014, it looked as if the mistakes of the previous year had been learned from as Angel Di Maria and Radamel Falcao were added to the ranks.
Neither worked out in the long run, but with their acquisition under his belt, the chances of Woodward signing the elite-level players needed to improve United's squad as they returned to the Champions League seemed positive.
In the end, though, United's summer saw them bring in just one established world star, and a fading one at that. Bastian Schweinsteiger's injuries and age had rendered him less important than he had previously been to Bayern Munich, so they let him go.
United's regime were successful in bringing in young up-and-coming talents, and in the case of Anthony Martial, they pulled off a masterstroke.
However, they failed to strengthen in the crucial area of centre-back, with Real Madrid's Sergio Ramos appearing to lead Woodward a merry dance.
As Hamish Mackay of the Mirror put it:
The warning signs were there, but United didn't see them. Woodward was convinced the club weren't being used as a pawn in the Spaniard's contract negotiations with Real Madrid. Unfortunately, that was exactly what was going on. Ramos has signed a new five-year deal in the Spanish capital and United are left feeling used.
United have strengthened in some areas, and the decision to play hardball with Real Madrid over David De Gea ended up bearing accidental fruit, but even Woodward's best window was a qualified success.
In January 2016, in spite of United's struggling season, no transfer action of note took place.
Commercially, the club remains a powerhouse, though it could be argued that has come at a cost to its soul—an intangible concept, but one which need not have been abandoned so thoroughly.
Perhaps that is a necessary evil in the modern football landscape, and Woodward has clearly executed this well—even if it feels tacky to see increasing numbers of sponsors' logos everywhere you look at Old Trafford.
Even that commercial success is qualified, though. United's share price has just hit a three-year low, per Sky Sports.
One positive note to sound would be that Woodward re-opened communication with fan groups, per Owen Gibson of the Guardian.
However, among a significant section of United's support, he will always be seen as part of the enemy—a man installed by the Glazer family after helping them structure the leveraged buyout of the club, per David Conn of the Guardian.
Most fans would still like to see him doing a good job now that he is in situ, but the transfers have been a qualified and occasional success at best. The managerial appointments have been disastrous. The off-field commercial activity has not offset the slump in share price.
Woodward is currently failing, and he needs to find a way to increase the on-pitch success to raise his grade and improve United's fortunes in the months and years ahead.