Andrea Radrizzani and Leeds’ relegation: His rise to power – and why he’ll shape club destiny - The Athletic 28/5/23

Phil Hay and Matt Slater

To look at Andrea Radrizzani in the tunnel before Leeds United’s penultimate home game against Newcastle United, it was as if the club were demob-happy and headed for a dead rubber in the sun.

He was relaxed and full of smiles, joshing with a group of mascots which included his son. He looked like a football club owner wants to look in the closing weeks of a season: calm and free of the weight of the world, like a Premier League chairman whose club are safe.

But around him, some of Leeds’ staff were speculating about whether they would see him at Elland Road again. Would it be the last time he was there as majority shareholder, six years after he first bought in? His body language disguised the fact Leeds were on the road to relegation and it was conceivable that if the following fortnight went badly, their final home fixture would be one for him to miss: too toxic, too flammable, a day when frustration might turn on him.

Radrizzani had been in tight corners at Leeds before, but this was different. Whereas last summer, after one successful relegation fight, the crowd were prepared to see if the Italian could bring the club to heel again, the 12 months since had exhausted patience and goodwill. A takeover was mooted and had been for months and it was difficult to find anyone inside Elland Road who did not think a change of ownership was overdue. Deep down, Radrizzani could see it too. But he had arrived on his terms and he would leave on his terms and with Leeds in danger of dropping out of the Premier League, all bets were off.

Running Leeds had given Radrizzani status beyond anything he had known before. Prior to investing in 2017, he was an entrepreneur with little or no profile outside niche media circles. He liked the exposure and he liked the attention but, as predicted in certain quarters, he was missing from the stands for today’s game against Tottenham, conspicuously absent as Leeds gave up the ghost and went down. Previously, his £45million investment in Leeds had risen tenfold to a level where the club were valued at half a billion pounds but at full time this afternoon, Premier League status was gone and so was that price tag. To all intents and purposes, the Radrizzani project has run its course. Leeds are back where they started.

From here, though, everything that happens will be shaped by Radrizzani’s next move. The offer of a takeover by minority partner 49ers Enterprises is still on the table, albeit at a significantly lower valuation. At the same time, it has been in his head that if he were to use parachute payments, incoming transfer fees and some of his own money to rebuild quickly in the Championship, he could guide Leeds back to the Premier League and peak value, irrespective of public opinion. In the end, a 56 per cent stake gives him control of the boardroom and those shares are his to sell or retain, his decision alone.

If he departs, he might dwell forever on how the legacy he wanted to leave behind crashed and burned; how a team who became the envy of others, blessed with a coach whose football was to die for, reverted to type and retreated into a web of incompetence. But is Radrizzani ready to leave with the 49ers waiting in the wings? Will his attempt to rescue stricken Italian club Sampdoria —his prime focus to the past week — cross the line? And at a club with a history of unpopular owners, how will history reflect on the man who appeared from obscurity after making a fortune in Italian media rights, broke the EFL ceiling, held a ripe future in the palm of his hand and then lost it again?

The story Radrizzani tells, his memory of the genesis of his decision to buy Leeds in 2017, is about a conversation with Kenny Dalglish a year earlier, on the day that Manchester City played Paris Saint-Germain in the quarter-finals of the Champions League.

Radrizzani had been invited to the tie and was in Manchester for lunch beforehand. There he met Dalglish, the Liverpool legend, and Radrizzani recalled how during a brief chat, Dalglish talked about Leeds being the English game’s most obvious investment. Here was a club with huge potential which had been allowed to wither for over a decade. Making the most of it would not be simple — United were notoriously prone to crises and were loaded with baggage from their financial collapse in the early 2000s — but the upside was that in footballing terms, they were relatively cheap. At most, they would cost in the region of £50million.

But how did Radrizzani have the money to invest? The tale starts in the Far East where his entrepreneurial instinct shaped his career from a standing start in Milan. That gave him a foothold in the sports media world, but it was the sale of the first business he co-founded, MP & Silva, which opened the door to football club ownership. The transaction was worth £532million ($661 million), affording him wealth on a new scale. He started thinking about acquiring a club and the conversation with Dalglish made him look towards Leeds, a club who already had an Italian owner in Massimo Cellino. A few months later, Radrizzani would be photographed with Cellino, sitting alongside him at Queens Park Rangers during Leeds’ first game of the 2016-17 season.

Radrizzani grew up in the village of Barbaiana on the west side of Milan, not a million miles from the San Siro. His father is said to have worked as an electrician, his mother for a TV network. Radrizzani attended IULM University, its main campus a short trip south around Milan’s ring road, where he studied media and public relations, producing one piece of work related to the structure of Deutsche Bank. But his interest after graduating gravitated quickly towards an area of business that was in its infancy and about to explode: the online and digital distribution of sports broadcasting rights. He was helped into that world by Rodolfo Hecht, who he met for the first time at a conference event. Hecht worked as president for Milan-based Media Partners, an Italian company who, in the late 1990s, were behind an early and ultimately doomed plan for football to create a European Super League. He was forever full of different ideas. Radrizzani has described Hecht as a “visionary”.

When Radrizzani took up employment with Media Partners, his initial roles were low-level and menial; an internship more than anything. Some of the work involved cleaning an office, some of it involved data entry. But he got to know Marco Bogarelli, a senior player at Media Partners and a highly influential figure in controlling and selling Serie A TV rights. Bogarelli, who died in 2021, came to be regarded as the gatekeeper to television money for Italian teams. Radrizzani was itching to spread his wings and, gradually, he talked Bogarelli into sending him to China, to a base in Shanghai, to help Media Partners’ new media arm, MP Web. It was 2002 and Radrizzani had secured his break.

At the time, the streaming of live sports events was highly primitive, constrained by poor-quality images and low internet bandwidth, but the potential for development was vast. MP Web began selling Serie A content to China and Japan. There was, remarkably, no collective TV deal in Italy and clubs were free to auction their own rights individually. MP Web took on the management of the official websites of teams like Sampdoria and Parma and Radrizzani, having seen the strength of the Far East market, helped to persuade the firm to set up a permanent office in Shanghai, to expand their reach there. An old associate of his, who did not want to be named in this article to protect relationships, described Radrizzani as having “all energy and ambition, so many ideas”.

His grounding in media rights would lead to the creation of MP & Silva, a company he launched with Riccardo Silva, another senior figure at Media Partners. Silva is now co-owner of AC Milan. Radrizzani had relocated from Shanghai to Tokyo and was doing work for Silva. He suggested to Silva that, rather than taking payment from him, they would use the money to set up a new media rights business. Other companies were trying to tap deeper into Serie A’s broadcasting potential and Radrizzani and Silva saw money to be made. Silva, a Brazilian entrepreneur, ploughed in some of his personal wealth. MP & Silva was born and its first headquarters opened in Singapore in 2007.

Over the course of almost a decade, its expansion was exponential. Initially, MP & Silva struck up partnerships with Italian teams and sold rights to Japan. Fiorentina were one and it helped to market them when the club signed Hidetoshi Nakata, the most famous Japanese footballer. Soon, MP & Silva was tapping into a huge range of sports and leagues, distributing rights around the world and positioning itself prominently in the field. At its height, it was turning over close to £1 billion annually.

Radrizzani began to connect with established industry figures and, in 2016, he was named as an advisor in the bid by the Suning Group to buy Inter Milan. Prior to that, most mentions of him had come in dry press releases issued by MP Web or MP & Silva. When it came to be sold in 2016, MP & Silva’s value had risen to more than £500million. The firm moved into Chinese hands, bought out via an investment fund called Jinxin.

What followed was a spectacular collapse in which MP & Silva lost lucrative rights agreements and plunged into liquidation. The High Court ordered the UK arm of the firm to be wound up in 2018, a mere two years later. Its Singapore branch entered provisional liquidation around the same time. The 2016 sale is now the subject of civil court proceedings in which Jinxin is attempting to recover the £532million it paid for MP & Silva. The group of people or parties it is claiming against includes Radrizzani, Silva and Radrizzani’s investment vehicle, Aser.

A High Court judgment published last November noted that among Jinxin’s allegations was one that MP & Silva’s retention of certain rights deals relied upon “bribes and other secret financial accommodations given to relevant decision-makers, combined with a series of unlawful and anti-competitive arrangements designed to avoid proper competition in the allocation process”. Radrizzani and the other defendants in the case deny all allegations of wrongdoing vehemently and the court document states their intention to “defend the claims in full”. The case is ongoing.

That original transaction, nonetheless, is what brought Radrizzani and Leeds together. Suddenly, he had the money to give football club ownership a go and the cash to tempt Cellino to part with Leeds. In effect, Cellino was a distressed seller, at odds with the crowd at Elland Road and drained after more than two fraught years in charge. Negotiations were tricky and almost collapsed at one stage, but in January 2017 Radrizzani bought in on a 50-50 basis. Within six months, Cellino exited with £45million in his pocket. The Radrizzani era was fully underway.

In the Amazon series Take Us Home, documenting Leeds’ 2019-20 promotion season, one of Radrizzani’s colleagues, Ruggero Magnoni, describes him as a man who likes to take “impossible bets” and, to a lot of people, Leeds were exactly that. They had imploded horribly from 2003 onwards. Every prior attempt to restore their Premier League status had failed. Radrizzani’s first experience of being in the boardroom at Elland Road was to see the club throw away a glaring opportunity to make the Championship play-offs. This was how it went.

He talked of supporting Juventus in his youth but his knowledge of the inner workings of a professional club was limited. In his early days as outright owner of Leeds, one of his closest advisors was Ivan Bravo, a Spaniard whose CV included a spell as a strategic director at Real Madrid. It was Bravo who recommended to Radrizzani that he recruit Victor Orta as director of football, an appointment which went through within a month of the takeover.

Bravo also suggested creating partnerships between Leeds and the Aspire Academy in Qatar and Cultural Leonesa, a lower-league club in Spain, both of which Bravo was actively involved in. Neither partnership bore fruit and as scrutiny on the point of them grew, they were mentioned less and less. After Marcelo Bielsa’s arrival as head coach in 2018, they were barely spoken about at all. Bravo resigned from Leeds’ board the following year. He continues to work as Aspire’s director general.

A mark of the Radrizzani era was the habit of engaging with side projects which generated negativity. He took the club on a post-season tour of Myanmar in 2018, a politically sensitive trip that drew attention to alleged human rights abuses there and went as far as attracting criticism from members of the UK parliament. Radrizzani was unapologetic, insisting “we can’t spread our values by turning our backs, we can only do this by engaging”. But publicity around it was not helped when Eleven Sports, a broadcast company owned by Radrizzani, subsequently secured broadcast rights to Myanmar’s national league, a decision the company defended saying the partnership would “ensure that we help the country develop its football infrastructure over a sustained period”.

A proposed change of Leeds’ club crest, meanwhile, was so unpopular and so roundly hammered that senior figures at the club had to talk Radrizzani down, despite his insistence that the change should go ahead. Roundly ridiculed, the design was abandoned in a matter of hours. Radrizzani maintained that the rebranding — based on the famous “Leeds salute” and created in the style of the Pro Evolution Soccer console game — could have worked for the club. Angus Kinnear, the club’s chief executive, later described the new badge as “shit”.

From the very beginning, though, Leeds needed Radrizzani’s cash. They were a loss-making club and at the height of their run to promotion, they were relying on him to plough in between £1million and £1.5million a month to cover operating costs. Certain players were used to raised funds — Ronaldo Vieira sold to Sampdoria for £7million, Pontus Jansson sold to Brentford for £5.5million, though Jansson’s exit in 2019 was largely down to Bielsa growing tired of the defender’s attitude — but between 2019 and the summer of 2022, the club were almost wholly reliant on shareholder cash and shareholder loans to cover shortfalls. Recently, that was what led to the most intense wrangling in the boardroom: with 49ers Enterprises yet to take majority control from Radrizzani but in line to do so, who was obliged to pay for what? How would the burden of transfer investment be split and who would meet future payments?

On the football side, Radrizzani’s tendency was to delegate. Kinnear, who also joined in the summer of the Italian’s takeover, was given responsibility for managing the finances and Orta directed decisions on the playing side, with a high level of influence over transfers and recruitment. When Leeds named Paul Heckingbottom as their head coach in February 2018, Radrizzani had been in the Far East for most of the preceding month. He appeared on the morning of Heckingbottom’s appointment to, as one person at Elland Road put it, “look in his eyes and be sure he was convinced”. Pursuing Bielsa later that year was Orta’s idea — as was the flawed punt on Jesse Marsch in 2022 — and, though Radrizzani was involved in one of the initial meetings with the Argentinian in Buenos Aires, negotiations fell to others in the senior management team. Likewise, it was Orta who often had the job of delivering news of a sacking, in one instance flying to interrupt Heckingbottom’s family holiday in Greece to tell him face-to-face that he was losing his job.

Radrizzani, though, could be forthright when he wanted to be. He would make appearances at EFL and Premier League meetings, even though owners tended to skirt them and leave them to chief executives or similar. He mixed closely with the squad whenever he was in England and many of the players found him to be good company, an affable chairman and fairly approachable. But in other moments he demonstrated his authority. The first time former head coach Marsch came under serious pressure the season, Radrizzani spoke at a gathering of the squad. The impression he gave them was that, far from losing faith in Marsch, he might offer him a new contract — a public show of faith. It was a way of saying that, when it came to it, the opinion that mattered most was his.

On occasions, that went for transfers too. Shortly after arriving as head coach, Bielsa told Radrizzani that by retaining Vieira, he would turn the talented midfielder into a £15million player. Radrizzani digested the advice but sold Vieira to Sampdoria for £7million anyway, using the money to pay for Patrick Bamford. More often than not, his patience with a head coach dwindled before that of those around him at senior management level. He was inclined to remove Heckingbottom’s predecessor, Thomas Christiansen, a month before he actually did. Bielsa’s dismissal in 2022 came two and a half weeks after the Italian first began pondering it. Marsch might have gone in January of this year had Orta not fought his corner after a 2-1 defeat at Aston Villa, buying the American another few games. Part of the reason for Orta’s departure as director of football a month ago was that in the wake of a 4-1 rout at Bournemouth, Orta was still backing Javi Gracia to keep Leeds up. Radrizzani and the board around him thought otherwise and the disagreement was irreconcilable.

What is obvious now is that none of Leeds’ choices of manager either side of Bielsa have worked at all. Bielsa was Radrizzani’s golden goose, even if Bielsa’s last season and his unceremonious exit badly damaged the relationship between club and coach. At no stage did Bielsa and Radrizzani have much of a personal connection. They would interact from time to time, like in the summer of 2019 when Bielsa chivvied Radrizzani via WhatsApp to sign Helder Costa from Wolves, but Orta was Bielsa’s main point of contact and Bielsa liked to keep himself tucked away at the training ground. Though Radrizzani was the money, the crowd saw Bielsa as the icon and the genius, an attitude which has hardened in the months since he left. It is a long-held truth in football that no child has posters of their club’s chairman on the wall. Murals are reserved for men like Bielsa, for players like Pablo Hernandez.

The success of appointing Bielsa was real and vivid, a unique moment in time. Interest and attention came from all quarters. In February 2020, as Leeds were starting to motor towards promotion, Bielsa invited two guests for a meal at Piccolino, an Italian restaurant in the Yorkshire village of Collingham. The guests were Pep Guardiola and Lorenzo Buenaventura, Guardiola’s fitness coach at Manchester City.

They ate steak and drank soft drinks, tucked away in their own little corner, Bielsa in a plain white T-shirt and Guardiola in a black zip-up. If time allowed, Guardiola would not hesitate to accept an invite from Bielsa. That was what Leeds had acquired: a head coach who the best of the best-loved and whose football served as a magnet, so easy to admire and enjoy. The club went up into the Premier League five months later and Bielsa’s little flat in Wetherby was swamped with fans on the night that it happened. It looked and felt like Leeds had hit the jackpot. It looked as if Radrizzani had all an owner could wish for; like he had won the impossible bet.

Around 18 months ago, people close to Radrizzani began asking the question of how much further he could feasibly take the club. He was wealthy, undoubtedly, but not at the obscene level needed to drive a Premier League team on year after year. The division required an inordinate amount of cash and, though Radrizzani had talked publicly about future growth — a new city-centre training ground, major redevelopment of Elland Road, staying on as majority shareholder until Leeds qualified for Europe — their struggle through the 2021-22 season cast doubt over the likelihood of any of that happening.

Criticism from the fanbase of him and Leeds’ stagnation grew and Radrizzani, a regular Twitter user, was acutely aware of it, keen for greater popularity or validation. Though some who worked with him would suggest that he come off the social media site or at least refrain from posting too much, he had a habit of tweeting in ways that aggravated the support. Last summer saw a shift in transfer policy too. Whereas in previous windows Leeds had made new signings without sanctioning major departures, this time they sold Kalvin Phillips and Raphinha for a combined total of close to £100million to finance their recruitment. “We cannot do another three years spending another £100million without any (transfer) income,” Radrizzani told The Athletic last August. Financially, they had their limits.

In terms of annual revenue, Leeds were consistently in a healthy position. In the 2021-22 financial year, their turnover reached a record £189million. But while that money covered a lot of their day-to-day costs, the view internally was that a minimum of £30m to £40m was needed via additional shareholder injections to allow for sufficient transfer activity. It was that which encouraged the feeling that, if Leeds were to progress, Radrizzani would have to relinquish them to 49ers Enterprises. The US fund, which was pulling together investors in the States, had the capacity to plough in more cash. And overall losses of £34million in the 2021-22 season showed how much a Premier League outfit swallowed.

Moreover, on the football front it was not going well at all. Leeds’ position as a competitive team under Bielsa had crumbled and neither the appointment of subsequent head coaches nor recruitment guided by Orta arrested the slide. Radrizzani was bullish at the start of this term, saying he expected Leeds to finish between 10th and 14th place. By the afternoon of a 4-1 defeat at Bournemouth last month, the final game of Gracia’s reign, he was describing himself in a Twitter message to a fan as “broken”. “I am responsible for this shit,” the message read. “Unacceptable. You don’t deserve this. Ridiculous.”

It is five years since 49ers Enterprises first came on the scene at Leeds, making an initial investment in 2018, but its intentions became more serious in 2021 when it upped its stake to 44 per cent and agreed an option to buy Radrizzani out in full, with a deadline of January 2024. Though the group sought complete control, it was mindful of not disrespecting Radrizzani or being seen to push him out prematurely. Then, in the early part of this season, 49ers Enterprises made it clear that it was ready to do the deal sooner. But it was aware of financial liabilities waiting down the line, some comprising of future payments owed for transfers, and it was not willing to pay quite as much as had been agreed in the 2024 option, one which valued Leeds at just under £500million.

In November, around the time of the World Cup, one member of the investment group was indicating that a transfer of ownership could happen before the end of the January transfer window but as time passed, there was no movement. The situation was complicated by the team’s second battle with relegation. In the EFL, 49ers Enterprises reckoned that Leeds would be worth closer to £150million than £500million, based on the drop in revenue they would suffer. At most, it would pay just under £170million. It was not prepared to finalise a takeover without relegation contingencies and an impasse developed, making the January window complicated. Every transfer involved negotiations about how precisely it would be funded. Orta, by then of the view that a takeover was essential, grew more and more frustrated with how slowly certain negotiations moved. A vacuum of leadership developed.

Georginio Rutter’s arrival from Hoffenheim was one example. Radrizzani mooted the idea of taking Rutter on loan with an obligation to buy at the end of the season but 49ers Enterprises wanted a permanent transfer immediately and a protracted move was done for £30million. Radrizzani favoured selling Jack Harrison to Leicester City, a means of raising around £20million, but 49ers Enterprises preferred to retain him and the move collapsed less than two hours before the deadline, despite Harrison being sent to Leicester’s training ground just in case. Events like those made the point that the split of ownership at boardroom level was not sustainable indefinitely.

Through further talks, Radrizzani and 49ers Enterprises got themselves a point where contracts were in place to allow a full takeover to go ahead this summer, contingent on Leeds avoiding relegation. Up until the 45th minute of the club’s game against Crystal Palace on April 9, it looked like they would do so. Leeds led 1-0 and were on course to move onto 32 points with eight games to play. They conspired to lose 5-1 by falling apart in the second half and had Radrizzani turned up in the directors’ box for today’s clash with Spurs, he would have been staring at a team who were stuck on 31 and as good as down. In the timeline of decline, it was a huge Sliding Doors moment.

On the Sunday of the Palace defeat, the marketing department at Elland Road were preparing for an announcement the following week. Leeds had been invited to join a pre-season Premier League tournament in the US and the six-team line-up for the event was about to be unveiled. But Leeds lost to Palace, the governing body got cold feet about whether Leeds would even be a Premier League team come July and, within 24 hours of the game, promptly replaced them with Fulham. Leeds were on the road to the Championship and would not get off it.

The spectre of relegation, and the realisation that it was probably coming this time, prompted 49ers Enterprises to initiate fresh discussions with Radrizzani about buying the club regardless of league status. Those negotiations have been ongoing for the past few weeks, urgent and tense. As time went on, the relationship between the two sides became more and more delicate and the US group is now clear on two things: that it will only buy at what it considers to be a fair price and that it wants Radrizzani to exit the building, as opposed to him continuing in an active, operational role as a minority stakeholder.

Additional challenges for 49ers Enterprises remain, even at this late stage. Not all of the investors behind its project are enthusiastic about buying an EFL side. The fund was put together on the basis of Leeds being a Premier League entity. A major call with the investment group took place this Thursday gone, with 49ers Enterprises still determined to bring a takeover to fruition in the worst-case scenario of relegation. But Radrizzani holds many of the cards, with the prerogative to stick to the price he wants or to plough on and try to get Leeds promoted again.

All the same, there is clear evidence of him looking for an exit plan. For a long time, he has had eyes on purchasing a team in Italy. Inter Milan are available to buy and Radrizzani has looked at their books, although the bank managing bids for Inter value the club at around £1billion and were not sure how he would fund that. In the past week, Radrizzani has openly declared his involvement in an attempt to acquire Sampdoria, a club who have bombed out of Serie A with horrible debts but, as a result, are more within his price range.

Radrizzani was videoed driving into Sampdoria’s training ground on Monday, indicating to local media that he was hopeful of completing a buy-out. On Thursday it emerged that Qatari Sports Investments (QSI) had involved itself in the process, offering to support a buy-out in Genoa. Radrizzani is close to QSI’s chairman, Nasser Al-Khelaifi, and at points in the past, QSI was vaguely credited with an interest in acquiring shares at Elland Road, without ever doing so.

A takeover of Sampdoria appears to hinge on Radrizzani selling Leeds, though, and progress on that front might be the tipping point for him and 49ers Enterprises to resolve and close out their own discussions. Yesterday, Sampdoria issued a statement announcing that the bid Radrizzani is part of had secured exclusivity to complete a deal. There was no sign of him or any of 49ers Enterprises’ representatives at Elland Road today.

There are other things in Radrizzani’s life beyond football — other assets he owns, like his investment firm Aser. Eleven Sports, the broadcast business he established, was recently sold to DAZN and he runs the Play for Change charity, an organisation which supports the underprivileged through sports and education projects. For a while he was a director of the football agency Football Capital but resigned from that position before investing at Elland Road.

But Leeds, by a distance, have been the biggest fish in his portfolio, the project which turned an unfamiliar media man into a recognisable face in the football world. And, six years on, it has taught him a lesson: that much like coaching and management, ownership often ends in disappointment, frustration and recrimination. Consolidating in the Premier League has been beyond him.

Leeds were never intended to be forever for Radrizzani and it easy to imagine him asking himself if he hung on too long; to imagine 49ers Enterprises thinking it waited too long to take the club from him; that through two very troubled campaigns, relegation has been coming. The city waits now to see how movement in the boardroom plays out because, for all that Leeds are without a long-term head coach, a director of football and a squad which is demonstrably ready for the Championship, nothing is sure to affect them more than the ownership structure from here on.

Three years ago, Radrizzani told Forbes that in future years he wanted to devote less of his life to business. “Let’s say that out of 100, the time I currently dedicate to work is 80 per cent,” he said. “I hope that in 10 years, it will be approximately 30 per cent family, 30 per cent for me, 30 per cent social projects.” A dabble with Sampdoria would make that very difficult, but as rising dissent rang around Elland Road for the final time this season, he must have been asking himself if the game at Leeds is up. In football club ownership, that question comes to them all.