Liverpool’s transfer business is usually smooth but after missing out on £115m Moises Caicedo to Chelsea and with Romeo Lavia snubbing them too, the pressure is really on to solve the ‘mess’ and deliver Jurgen Klopp a midfielder

One of the hallmarks of the John W Henry era at Liverpool was success in the transfer market.

Liverpool have learned from early mistakes, such as Mario Balotelli, and have since scored more wins than defeats.

Smart recruits Mo Salah, Virgil van Dijk and Alisson helped Jurgen Klopp build a team to win every major competition.

But that carefully built reputation is in danger of imploding after a terrible week for Liverpool’s transfer chiefs.

If missing Moises Caicedo to Chelsea was a major blow, it would be hugely embarrassing to meet the exact same fate with their next target, Romeo Lavia.

Now Southampton midfielder Romeo Lavia appears to be doing the same and signing for the Blues

It represents another setback for Liverpool manager Jürgen Klopp in his search for a midfielder

Klopp has always been keen to make a unified voice at Anfield, but he will be aware that signing a top-class midfielder could be the difference between facing a title challenge this season, or not.

Club legend Jamie Carragher, who is normally sympathetic to Liverpool’s stance, has not held back seeing his club outperformed by Chelsea’s brash owner Todd Boehly.

“An absolute mess and a joke,” is his description of how the situation has been handled at Anfield.

After the loss of midfielders Jordan Henderson, Fabinho, Naby Keita, Alex Oxlade-Chamberlain and James Milner in one fell swoop, people had hoped for a smoother succession.

Yes, Alexis Mac Allister has arrived from Brighton alongside Hungarian Dominik Szoboszlai, but the Argentina World Cup winner was forced into a defensive role in the opening game against Chelsea and was not his usual self.

“Liverpool are in a pretty difficult position right now. People know they are desperate,” Carragher added.

The timeline of events is strange. Klopp sang Jude Bellingham’s praises in January, but in the summer Liverpool decided they couldn’t compete financially and the player joined Real Madrid.

But after chasing Lavia from Southampton all summer without meeting the £60 million asking price, they suddenly offered a British record £111 million for Caicedo in Brighton.

The departure of Jordan Henderson, Fabinho and others has left a gaping hole in midfield

Jamie Carragher destroyed the Liverpool transfer business after missing out on two big signings

Carragher said he ‘didn’t know what was going on behind the scenes’ after Michael Edwards (left) and his successor both left the club

Caicedo had always intended to join Chelsea, whose director of global talent Paul Winstanley used to work at Brighton and was instrumental in getting Caicedo to his first club in England.

If Liverpool thought their intervention would drive up the Caicedo price and take Chelsea out of the race for Lavia, it was a risky strategy that has so far failed to pay off.

Despite Liverpool being late in meeting Southampton’s terms on a transfer fee, it is now rumored that Lavia would also prefer Chelsea, whose money-spending ambitions know no bounds.

The London location may be one aspect, but the youngster may also have been upset by Liverpool suddenly shifting his focus to Caicedo.

Whatever happens next, it’s not the smooth way Liverpool like to do their business.

Liverpool decided their original midfield target, Jude Bellingham, was too expensive

Liverpool managed to sign a deal for Alexis Mac Allister from Brighton earlier this summer

Hungarian Dominik Szoboszlai also signed, but Liverpool still need new midfield recruits

The recent failures in the market have put a lot of pressure on CEO Billy Hogan

The spotlight will fall on the Liverpool staff behind the scenes.

Respected sporting director Michael Edwards left in 2022. His replacement Julian Ward announced later that year that he would step down at the end of the 2022–23 season.

It has placed a lot of pressure and responsibility on Chief Executive Billy Hogan, a longtime associate of club owner FSG.

The early acquisitions in the window of Mac Allister and Szoboszlai suggested business as usual.

Then the Saudi intervention, with both Henderson and Fabinho leaving, left a huge hole in the midfield base. So far, a week into the season, it is still not filled.

Until they do, questions will be asked and Carragher’s claim of a “mess” will be hard to refute.