Chelsea's proposed £4.25 billion ($5.2bn) takeover could 'fall apart' according to a UK Government insider, who has said the deal could run out of time.
Los Angeles Dodgers co-owner Todd Boehly has already agreed on the terms of a deal, backed by private equity from Clearlake Capital, and alongside several other billionaires.
However, with the Premier League conducting due diligence on Boehly to complete the sale, there are concerns about where the money ends up.
What is the problem with Chelsea's takeover?
Chelsea currently owes £1.6 billion ($2bn) to their owner Roman Abramovich's company Fordstam Limited. In turn, they owe a similar sum to Jersey-based Camberley International Investments, which has suspected links to Abramovich.
However, statements published on the European champions' website on behalf of the current owner Roman Abramovich, who is currently sanctioned due to alleged closeness to Russian President Vladimir Putin, have said that he is going to write off the debt.
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"I will not be asking for any loans to be repaid. This has never been about business nor money for me, but about pure passion for the game and Club," one statement read on 2 March.
A day later, he revealed that he wanted all of the proceeds of the sale would go to "the victims of the war in Ukraine".
These actions have been disputed by Government sources who believe that Abramovich could seek to claim the capital through his complex network of companies.
"Two big sticking points remain - where exactly the proceeds of the sale will be held, and what legal guarantees government will be given about the money going to good causes," they said.
In a statement to the BBC, an insider added: "Essentially, despite committing to all proceeds going to good causes in public, Abramovich seems unwilling to give the same legal commitments, which would have backed up his public statements of about a week ago, that in the deal neither he nor his affiliates could basically try and stake a claim to that unpaid debt between Fordstam and Camberley.
"A deal which would allow the cash to be diverted during the deal would be a breach of sanctions and is seen as a red line for ministers.
"There are deadlines at the end of this month and the start of June, which would either see the club booted out of European competition or the Premier League entirely. But a good chunk of the sale needs to be done this week or next."
What does it mean for Boehly's takeover?
When contacted, sources within the Boehly-Clearlake camp remain calm and are relying on the Government to resolve issues around where their purchase price ends up.
There is concern that this situation could see the club used as collateral in a political game between a sanctioned individual and those who have issued the penalties.
Ultimately, should the takeover go into June, it could hinder Chelsea's ability to register for next season's Premier League and UEFA Champions League competitions, as well as cause issues in the transfer market.
It would propel them into a new level of crisis, far beyond their current concerns as they operate under a special licence.