Mathieu Flamini has dashed Arsenal's faint hopes of keeping him by agreeing to join Milan, while the Premier League club face a crunch meeting over Alexander Hleb's future later this week.
The signs are that Arsene Wenger will be shorn of half his first-choice midfield - and two of his best performers this season - with Hleb having been offered a huge four-year contract by Internazionale, Milan's city's rivals, which he is keen to sign.
The loss of the pair would be a severe blow to Wenger who has set Flamini a deadline of the end of this month to decide his future after making what he described as a "decent" improved offer. The 24-year-old French midfielder's present contract runs out on 30 June and, despite Arsenal's efforts, he has been offered far more by Milan and Juventus.
It had appeared that Juve were the favourites to sign Flamini but they have been out-bid by Milan who are willing to pay him four million euros a year - a million more than was an offer from their rivals - which includes a significant signing-on fee spread over a five-year contract. They have ear-marked Flamini as the eventual replacement for Gennaro Gattuso - which is ironic considering the midfielder was nicknamed after the Italian by his Arsenal team-mates.
Over the weekend Carlo Ancelotti went public on Milan TV - the club's own television channel - to speak of his admiration for Flamini, especially after the way he performed against the European Cup holders in the Champions League tie earlier this season. Flamini - whose father Roland is Italian and has relatives in Rome - is free to talk to other clubs because his contract has almost expired. He has made clear that he wants to accept a more lucrative offer than has been tabled by Arsenal, especially as Flamini has felt under-valued at the Emirates for some time. Wenger has urged Flamini not to leave Arsenal just for a "few bucks" but that kind of comment will not be well-received by his player.
Hleb, who is 27 next month, has been offered an impressive four-year deal by Inter, but will hold talks with Arsenal this week. He is understood to be concerned that, after so much promise this season, it is now the third campaign in a row that Arsenal have failed to win a trophy. Much to Wenger's annoyance, the Italian champions have openly declared their interest in the Belarussian who joined Arsenal from Stuttgart in July 2005. He has two years left on his present deal but article 17 of FIFA regulations would allow him to leave for a fixed fee, likely to be significantly less than the £11.2m Arsenal paid for him.
The situation presents Wenger with a major headache. His team face bottom club Derby County away tonight with Flamini a doubt because he has not fully recovered from an ankle injury. Wenger may have a league debut to goalkeeper Lukasz Fabianski who, he said, will vie with Manuel Almunia for the club's number one slot next season.