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Barcelona target Philippe Coutinho has submitted a formal transfer request to Liverpool, defying the Premier League club's insistence that they will not release him, a British newspaper reported on Friday.
After reports that Liverpool had rejected a second bid worth 100 million euros ($117 million) from Barcelona, whose 80 million offer for the 25-year-old attacking midfielder had been rebuffed last month, the club's ownership group released a statement.
"We wish to offer clarity as regards our position on a possible transfer of Philippe Coutinho," Fenway Sports Group said.
"The club's definitive stance is that no offers for Philippe will be considered and he will remain a member of Liverpool Football Club when the summer window closes."
But shortly afterwards, the Liverpool Echo reported that Coutinho had sent an email to Liverpool's sporting director Michael Edwards expressing his wish for a move.
Liverpool did not respond to a request for comment.
In releasing their statement, the club hoped they had taken a tough enough stance to end further talk of a move.
Instead, they had upped the ante less than 24 hours before their Premier League opener against Watford, a game for which manager Juergen Klopp said the Brazilian was injured.
For many on Merseyside, the scenario is eerily familiar, with Fernando Torres, Javier Mascherano, Xabi Alonso, Luis Suarez and Raheem Sterling all leaving when the club hoped they would stay.
This time, Fenway and Klopp have both invested personal capital in facing Couthino and Barcelona down.
At much the same time as Coutinho was preparing his email, Klopp was saying: "Liverpool is not a club that needs to sell. That is set in stone ... No price at which we are ready to give in."
The test of that statement will come over the next couple of weeks. But Liverpool know that even if Barcelona return with a third bid in excess of 100 million pounds, it is probably too late for them to spend the money sensibly.
The Reds have already failed to secure their two primary targets in the transfer window, Naby Keita and Virgil van Dijk. Trying to land a comparable replacement for Coutinho, last season's top scorer at the club with 14 goals, is likely to be even harder.
To add to Klopp's discomfort, the only Liverpool player to rival Coutinho's creativity, Adam Lallana, is out injured for at least two months.
So even before a ball has been kicked, Klopp's problems were already mounting.
Much the same happened to Liverpool almost exactly four years ago when Arsenal bid for Suarez, who said he wished to go.
On that occasion, owner John W Henry also played hardball, effectively forcing Suarez to stay for another year, until Barcelona came calling with a better offer.
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