The Blues have had a miserable season so far, with Jose Mourinho paying the price with his job and the club turning to old friend Guus Hiddink to stop the rot.
They have been a far cry from the team that eased to the league title last year, and their miserable first half of the season could cost them in their bid to bring Bale back to the capital.
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With Eden Hazard failing to replicate the form that saw him crowned PFA Player of the Year last term, Chelsea are reportedly considering using the Belgian as leverage to sign a marquee name.
Despite helping the club to win La Decima in 2014, the dominance of Luis Enrique’s Barcelona has paid a significant role in the Madrid fanbase losing patience with their world record signing.
There remain question marks over his relationship with Cristiano Ronaldo, whose influence in the dressing room is such that he still expects to be the talisman of the side regardless of Bale’s higher price tag.
Such struggles have prompted talk of a move to Louis van Gaal’s flailing Manchester United, but despite the Red Devils’ lingering interest, Chelsea have the perfect bargaining chip in their attempts to land the Welshman.
Chelsea have been consistently linked with a move for Juventus’ Paul Pogba, but Bale would be the ideal signing to numb the pain of Mourinho leaving the club for a second time.
Willian is the only one of the club’s three wingers – Pedro being the other – to display his best form and Bale’s arrival would offer them increased potency on the flanks in place of Hazard.
The Belgian has looked disinterested from the start of the season and is yet to break his goal duck with his last strike coming last May.
He was dropped for the later matches in Mourinho’s reign, and is yet to sparkle into life during Hiddink’s brief stint at the helm.
Chelsea have proven in the past that they can usurp their rivals by landing the players swiftly and without a protracted transfer saga.
They leapfrogged rivals Tottenham to the signing of Willian in the summer of 2013 and then pipped Liverpool to Egyptian winger Mohamed Salah the following winter.
However, they could face a difficult time of doing the same if they fail to secure Champions League football, which was one thing that prompted Bale to leave for Madrid during his days at Spurs.
If they are unable to reach Europe’s top-tier competition then they will lose him to United, who could proceed to rediscover the swagger of old regardless of Van Gaal’s demanding style of management.
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