What Chelsea must prove as they return to scene of biggest humiliation

The blue billion-pound bottle jobs return to the scene of the crime. Or one of the crimes, anyway. For Chelsea, a second visit of the season to Wembley is an unwanted reminder that they can snatch ignominy from the jaws of respectability, that they can seem embarrassing when they could otherwise be impressing. Sadly for them, it may not be necessary. The selfishness of the petulant pair of Nicolas Jackson and Noni Madueke, squabbling over a penalty against Everton on Monday that was clearly meant for Cole Palmer, would add another dimension to a shootout against Manchester City at Wembley on Saturday: with the pressure on, would anyone other than the nonchalant, nonplussed Mancunian step up, let alone prove so eager to wrestle the ball off a teammate to volunteer their services?

Wembley, the first half of what could have proved a cup double, highlighted other questions about their mentality. Gary Neville’s infamous jibe at Mauricio Pochettino’s team stemmed from extra-time, as Jurgen Klopp introduced ever more unknown and inexperienced players and yet Liverpool won the Carabao Cup.

Which means that Chelsea still await the first trophy of the Todd Boehly era. They crossed the £1bn barrier in spending even before it was known they sold a hotel to themselves for £76m to ensure they passed profitability and sustainability rules (PSR). If Saturday provides City with the rarity of a day when – relatively speaking – they are the small spenders, it is a game that could bring the best out of Chelsea. After all, they have drawn twice with Pep Guardiola’s side this season: a 4-4 at Stamford Bridge was clinched by an injury-time Palmer penalty and showed the greater attacking incision Pochettino has given them; while a 1-1 at the Etihad Stadium brought a defensive resilience Chelsea have rarely displayed in conceding 15 times in their last eight fixtures.

Their worst side has been apparent recently, and not merely when a 6-0 evisceration of Everton was marred by the immature insubordination of Jackson and Madueke. Chelsea contrived to lose a lead and draw with 10-man Burnley. They contrived to lose a lead and draw with doomed Sheffield United. And if their fortunes since Wembley are not all negative, that highlights their erraticism.

They have reached Wembley courtesy of a fifth-round 90th-minute goal – from Conor Gallagher against Leeds – and a quarter-final brace in added time, courtesy of Madueke and Carney Chukwuemeka against Leicester. Neither was still as late as their ludicrously anarchic win over Manchester United, sealed by Palmer in the 101st minute.

If that game seemed a one-off, it conformed to a wider theme. Chelsea can represent an enigma but this fallen giant often performs best against its former peers. Count their penalty shootout victory over Newcastle as a victory and their record against the top seven this season consists of five wins, five draws and five defeats. Two of those losses were 4-1 humiliations but the others were only by one goal. Chelsea compete on such stages, but, with varying degrees of incompetence, they have also lost to Middlesbrough, Brentford, Everton, Nottingham Forest and twice to Wolves.

All of which may get to the heart of an identity crisis. Are Chelsea a good team against the good teams and a poorer side against the weaker sides? Monday was the latest evidence to suggest they aren’t a team at all, just the phenomenon of Palmer and a bunch of mismatched and very expensive players. A curiosity of the rout of Everton was that Enzo Fernandez was missing: for the £222m double act of the Argentinian and Moises Caicedo, Boehly could have bought three of Chelsea’s hotels from Chelsea. Fernandez and Caicedo, however, have both ensured that Jack Grealish no longer has the status of the most costly player in the Premier League.

Their rather cheaper predecessors, N’Golo Kante and Jorginho, started when Chelsea last beat City: in the 2021 Champions League final, in the third of three victories for Thomas Tuchel over Guardiola in the space of six weeks. It was another era: Roman Abramovich’s Chelsea, when they dealt in the currency of trophies, when they seemed a winning machine.

That, perhaps, was what Boehly thought he was buying. Although, given his record in recruitment, who can be fully sure? But as City’s aims have been downgraded to a double, as Chelsea look to save their season with silverware and qualify for Europe, only to presumably fail Uefa’s more stringent financial fair play tests, the burden of proof rests on Pochettino and Chelsea to show they have the bottle, the capacity to capture a moment rather than capsizing their own chances. Their flurry of goals against City this season represents progress in itself – Chelsea lost four times to Guardiola’s team under Graham Potter and Frank Lampard last season, failing to score in each – but their ability to regress to a laughing stock in an instant presents a warning. And Wembley shows how it can go very wrong for them.