Omar Berrada does not always follow the path of least resistance. The same can be said of any individual joining this crumbling current iteration of Manchester United.
However, long before agreeing to leave reigning treble holders Manchester City to grab a bucket and begin bailing out a leaking Old Trafford, Berrada went against the grain.
"A common theme of my career has been to take risks and to try things and to be part of a journey," the French-Moroccan executive explained. "And the journey can go well, it can go badly, but you get to learn and experience things."
It remains to be seen how well or woeful Berrada's time at United is, but here's what the club's incoming CEO has learned along the way.
Football fan
Within minutes of the news of Berrada's appointment circulating, the internet's fleet of detectives dredged up any vaguely incriminating social media posts. The best that the first wave of vigilante stalkers could find was Berrada aiming a jibe at Manchester United at the start of 2013.
City's then-executive wryly mused that Bayern Munich were the better side in the 1999 Champions League final which United famously won with two stoppage-time goals. This harmless poke is far less interesting than Berrada's claim to have been watching a repeat of the showpiece event more than a decade later.
As chief football operations officer at City Football Group, the elite organisation across the sport, Berrada has had no shortage of interview requests from companies trying to tease out secrets of success. Almost without fail, Berrada makes it clear that: "Working in football is a dream."
When Berrada's boss at telecommunications company Tiscali (now known as Tessellis) was hired as Barcelona's chief marketing officer in 2003, he leapt at the opportunity to follow him to the club he grew up supporting. "I probably would have accepted to join Barcelona for free," Berrada joked, "so I was lucky they offered me a salary."
Integral part of Man City's hierarchy
When Berrada joined Manchester City in 2011, the club had not won a top-flight title since 1968. After convincing his family to initially move to London - "I still don't know how I persuaded my wife to exchange the Barcelona weather for the UK weather," he later reflected - Berrada joined City's International Business department before getting bumped up to director of partnerships in 2012.
In 2016, Berrada climbed the ladder again, taking on the lofty mantle of City’s chief operating officer. As COO, Berrada soon began to assist City’s vaunted sporting director Txiki Begiristain with transfers. Berrada was part of the sky-blue squall dispatched to Monaco to negotiate a move for Erling Haaland, beating out "almost all the top teams" by his own estimation.
By 2020, Berrada was promoted to chief football operations officer of the wider City Football Group, which includes clubs dotted across four different continents. By comparison, managing the mess at just Manchester United should be relatively straightforward.
Berrada not only brings extensive experience of footballing bureaucracy but specifically that of United's closest rivals. After a decade embedded in the club, Berrada has an intimate working knowledge of City's entire operation, including everything from bonuses and salary scales to Pep Guardiola's go-to order at Manchester's Catalan restaurants.
Looming spectre of Man City's financial breaches
As with any supporters of rival Premier League clubs, United's fanbase are always quick to point towards the looming 115 financial breaches City have been accused of in response to any on-field success from Guardiola's side.
City strenuously deny the Premier League's charges and won their case against UEFA when European football's governing body initially banned them from the Champions League in 2020. However, the trial is looming and the Premier League's case will not be hampered by the statute of limitations which undermined UEFA's allegations.
Among the numerous breaches, City have been accused of artificially inflating sponsorship payments, with companies allegedly funded by the club's owners behind injections of capital to circumnavigate financial fair play regulations.
During the window of these breaches, which stretches between 2009 and 2018, Berrada held positions at the club relating to commercial sponsorships. Both The Times and The Athletic claim that there is no suggestion that Berrada is implicated in any malpractice and Manchester United must have been satisfied with their own background check.
Balance between football and business
Berrada has described the "biggest challenge" of his role as finding "a balance between the football side of the operation and the business side".
"In many ways, they operate in two different worlds," Berrada explained, "but the reality is that you need to be able to bridge that gap to operate as a unit."
While 'executive vice-chairman' Ed Woodward was effectively United's chief executive for the first decade of the post-Sir Alex Ferguson era, the club was quite obviously geared far too closely to the business side of proceedings. United may have had an official mattress and pillow partner but they lacked the players and sporting structure to awaken this sleeping giant.
Berrada is United's first outside hire for the CEO role and will be taking over from the interim operator Patrick Stewart, the head of the club's legal department. Rapidly redressing this skewed balance between football and finance will be Berrada's first task - as United felt compelled to outline in his welcoming statement.
"The club is determined to put football and performance on the pitch back at the heart of everything we do," United's press release read. "Omar's appointment is the first step on this journey."
That football wasn't the already main focus for Manchester United FC underscores quite how difficult Berrada's latest challenge will be.
