It was the photo opportunity they were all waiting for but the handshake between the mysterious new co-owner of Milan and representatives of Suning, the Chinese conglomerate who purchased Internazionale last year, never materialised. Eight thousand miles away in Beijing, as the two clubs with 36 scudettos and 10 European Cups between them played out a 2-2 draw at San Siro last month, tongues were already wagging.

Confirmation Li Yonghong had completed his protracted takeover of Milan a few days before the derby della Madonnina was also greeted with scepticism by some in the Italian press. Far from being the beginning of a shiny new era that had been painted by the former owner Silvio Berlusconi after more than three decades at the helm, Alberto Costa, the experienced Milan correspondent for the Corriere della Sera, admitted on Italian television he had major doubts over the new owner.

“I’m not sure this new Milan have the resources to get back to winning,” he said. “There are debts to be covered and Milan will not make enough to cover them.”

The unusual structure of the deal – which had Li’s Hong Kong-based Sino-Europe Sports Investment pay €100m as a deposit last June before three further payments totalling €150m – has raised the most eyebrows. Having at first claimed the takeover was backed by the Chinese government (the press release from Berlusconi’s company Fininvest to announce the deal contained a reference to the Chinese government’s State Development and Investment Corporation that was later removed), Li revealed a few days before he was due to pay the remaining balance on a deal worth a total of €740m, including debts, that it would now be completed using a different holding company based in Luxembourg called Rossoneri Sport Investment.

Chinese-owned clubs in Europe Aston Villa Tony Xia, Recon Group (100%) Birmingham City Paul Suen, Birmingham Int’l Holdings (50.6%) West Brom Guochuan Lai (100%) Wolves Guo Guangchang (100%) ––––––––– Auxerre James Zhou, ORG Packaging (60%) Nice Alex Zheng & Chien Lee (consortium also inc US businessmen 80%) Sochaux Wing Sang Li, Ledus (100%) ––––––––– Internazionale Zhang Jindong, Suning Holdings Group (68.55%) Milan Li Yonghong – RSI (99.9%) ––––––––– Espanyol Rastar Group (56%) Granada Link Int’l Sports (100%)

“Following a deep analysis, a new structure completely external to China has been defined in order to complete the transaction,” explained a Milan statement. “The buyers have confirmed their commitment to make important efforts to recapitalise and strengthen the capital and financial position of AC Milan.”

Just before he completed the takeover, it also emerged Li had taken out a loan of €300m from the US private equity fund Elliott Management – which has been described as “a vulture fund” owing to its tendency to lend money to failing companies – to finalise the purchase and to help the club to cover short-term payments, an agreement that, according to a Reuters source, contains “some form of guarantee” over the financing. At an interest rate of 11.5% on capital that must be repaid by October 2018, it is a hefty risk to take on.

“The Chinese government has recently placed restrictions on outbound foreign investment because they might suspect it is an excuse to move capital overseas,” says Alain Wang, a journalist for the Chinese newspaper Titan Sports who has lived in Italy for 13 years. “That is why Li Yonghong had to find alternative sources of funding at the last minute. Commerce is one thing because you import and you export. But to buy a football club is really different because it is impossible to make a profit in the near future. It’s like a big hole – you keep on filling up with money.

“What will these people do in the near future if they want to get some money back? There is no other possibility than investing in the real estate market using the name of Milan. I expect them to do something like construct a ‘Milan City’ with new shops and apartments. It’s impossible to think just because a Chinese person has bought the club everyone in China will go out and buy a Milan shirt.”

Casa Milan, Milan’s headquarters, before a press conference with the Chinese investors “Rossoneri Sport Investment Lux” on April 14, 2017 in Milan. Photograph: Miguel Medina/AFP/Getty Images

Joining Li on the new board of directors will be his right-hand man Li David Han, Bo Lu, chairman of the venture capital fund Haixia Capital Management Co, who had been part of the original investment group, and entrepreneur Xu Renshuo. There will also be four Italians on the board: Marco Patuano, who has been the chief executive of Telecom Italia since 2011, lawyer Roberto Cappelli, who assisted Li in the negotiations, the former Inter CEO Marco Fassone and Paolo Scaroni, the former chief of the Italian energy company Eni and a close ally of Berlusconi. New club statutes each resolution requires “a favourable vote from a number of Italian directors that is at least equal to half the voters” on the board who are in favour of the resolution.

“Scaroni was already a minor shareholder at Milan and it is curious he has remained under the new owners,” says Pippo Russo, a sociologist from Florence University who specialises in the business of football. “I don’t know if this could mean Berlusconi still wants to have an influence in some manner but I’m sure in the next few weeks and months we will have a clearer picture of what is happening.”

Details about the source of Li’s fortune have been particularly difficult to verify. He is believed to own a 28% share in Renshuo’s New China Building project in Guangzhou – a 48-storey development of offices and shops that is estimated to be worth around €1bn – and has also owned shares in packaging companies and phosphate mines.

There have been allegations against Li’s family which could also explain Suning’s reluctance to engage with him and his entourage at the Milan derby. In 2010, Shanghai Zhengquan, a financial newspaper owned and run by the Xinhua state news agency, reported they had been at the centre of a so-called “pyramid” scam that led to more than 800 investors losing £90m in a company called Jade Valley Development. Li’s father Naizhi and his younger brother Yongfei were sentenced to prison by Huazhou City people’s court for the “illegal absorption of public deposits” but evaded arrest by fleeing to Hong Kong. As one of the listed shareholders, Li Yonghong’s name was kept on file by the government’s financial watchdog, although he has always denied his involvement.

Public records also show Li was fined in 2013 by the China Securities Regulatory Commission after reneging on a deal not to sell his stake in Shanghai Duolun Industry Co – a real estate and building materials company – and failing to make the sale public. Asked to explain by Fininvest, Li said it was just a warning and he had eventually released details of the sale. Nonetheless, the revelations caused a storm in Italy as the media began to question his motives for buying Milan.

Mino Raiola, the agent of Milan’s highly rated Gianluigi Donnarumma, has hinted that the goalkeeper will not sign a new contract until he knows ‘what Milan are going to become’. Photograph: Tullio M Puglia/Getty Images

“The Italian press was running behind any hypothesis and totally lost the capacity to analyse the situation,” Russo says. “That explains why at this moment when it should be necessary to scrutinise the profile of Li Yonghong there is nobody doing it. I can’t understand it. Milan is a massive part of the narrative of Italian football and also a symbol of national pride. Everyone has just been focused on the positive aspects – Milan has a new owner and could be about to return to the glory days. But this is, in my opinion, a distortion. Or, as Donald Trump says, alternative facts.”

“Since the beginning, my newspaper has always been saying things that are contrary to what is being said in the Italian press,” Wang adds. “It was always said Chinese capital was buying Milan because the Chinese government wanted this. For six months these were the kind of reports that were in the serious newspapers here.

“Now everybody has suspicions about what is going on regarding their capability to fund the takeover and also who is behind it. But surely Berlusconi should have known there were issues at the time? Or at least he should have done some due diligence. I think he just wanted to sell up and didn’t care about what happened afterwards.”

In his statement confirming the sale last month, however, the former Italian president said he was leaving Milan “with pain and emotion, but with the awareness that to compete in modern football at the highest European and world levels needs investment and resources that a single family can no longer support”.

Silvio Berlusconi, left, and Adriano Galliani attend the Serie A match between Milan and Inter in November last year. Photograph: Claudio Villa - Inter/Inter via Getty Images

It is six years since Milan won the title and they have struggled to keep pace with traditional rivals Juventus under coach Vincenzo Montella. Despite Li’s insistence that he is an integral part of the club’s future, Mino Raiola, the agent of goalkeeper and crown jewel Gianluigi Donnarumma, hinted in February that the teenager would not commit to a new deal until he had seen “what Milan are going to become”. But despite reports last week they have agreed a deal worth £20m to sign the Switzerland full-back Ricardo Rodríguez from Wolfsburg, according to Russo, it may not be long until they are up for sale again.

“Elliott is a vulture fund so they will not be interested in investing in Milan,” he says. “Eventually, they will become the real owners and the whole process will start again.”

Wang adds: “When the Glazers bought Manchester United using finance it was almost a guaranteed revenue stream. But Milan and Inter are different because every year they lose a lot of money – for example, last year Milan lost €90m. Suning is a big group in China so they can use it to help with things like advertising, although they have not been so hasty in opening a commercial network in Europe yet.

“But the people from Milan have been so secretive. I’m sure that behind Li Yonghong there are many other Chinese investors who will not reveal their names.”

Li has insisted that is not the case and, with the club’s debt now reduced to €190m, believes Milan will at least be self-sufficient for the new season. It remains to be seen how far their new owner’s funds will stretch.