Carlo Ancelotti, the decorated manager who is suing his former club Everton, held discussions with a controversial Russian oligarch about a series of incentive payments that were dependent on Everton’s performance in the Premier League. The Russian-Uzbek billionaire Alisher Usmanov proposed the bonuses at about the time Ancelotti was in talks to take the Everton job in 2019, sources say. The suggestion raises questions about whether a proposed side deal between Ancelotti and Usmanov is behind the manager filing a claim against Everton in London’s high court. The talks will also add to the repeated intrigue over Usmanov’s alleged influence over Everton’s owner, Farhad Moshiri, with football regulators and fans likely to be curious about anybody other than a club’s owner or directors offering incentives to a coach. Usmanov’s spokesperson said: “In his personal interactions with Mr Ancelotti, Mr Usmanov, as the largest shareholder of the club’s main sponsor, discussed the hypothetical possibility of creating an additional bonus fund for the club in the event that the latter achieved a significant success – namely, entering the League of Champions [sic] – an event which, as we know, did not ultimately take place. There were no legally meaningful arrangements made in this regard, while the club’s results were far from even being considered a success.” Further sources suggested to the Guardian that the high court claim concerns a bonus that Ancelotti believes he negotiated with an individual outside the club, and that one target may have included a top-half finish, which Ancelotti did achieve in the 2020-21 season. One former Everton director said the Italian, now the coach of Real Madrid, had been “promised something … and now it clearly hasn’t gone away”. It is understood that Everton’s position is that no bonus payments were offered on behalf of the club and that it would not have authorised any such payments. Ancelotti’s legal case – which relates to “general commercial contracts and arrangements”, according to the claim filed at court, was first reported by the Guardian on 12 June. The club is facing the legal claim at a time when its board has just one member – the chairman, Bill Kenwright – after Everton were hit last week by the resignations of three directors. More than a week later, none of the directors have been replaced, but the club have issued a statement implying that new appointments are imminent. The connections between Moshiri and Usmanov have long been a source of controversy. This has included a series of managers raising fresh questions in January over the ownership of Everton, after claiming they were interviewed for the top job in the presence of the oligarch. Usmanov was barred from entering the UK by the Home Office in 2021, at a time when companies in which he was the largest shareholder were major sponsors of Everton. At the time, the club said it was aware that Usmanov had been barred from the UK but that the club had not broken any laws or Premier League rules. Usmanov had sanctions imposed on him by the Foreign Office last year after Russia’s invasion of Ukraine, when Everton announced it had cut ties with the tycoon. When the sanctions were imposed in March 2022, he described the Foreign Office citation as “false and defamatory allegations damaging my honour, dignity and business reputation”, and vowed to fight it. Responding to the Guardian’s questions about discussing bonuses with Ancelotti, Usmanov’s spokesperson said the tycoon “has always carefully observed the Premier League’s rules and legal requirements. He has never, and could never, make any decisions within FC Everton.” Everton, Moshiri and Ancelotti did not provide a comment to the Guardian.