There was no time this summer for Todd Boehly to ease into his role as Chelsea's interim sporting director. And the transfer window has proved something of a crash course for the American billionaire, who fronted the group that bought the club from Roman Abramovich at the end of May.
Yet nothing Boehly has experienced thus far will have truly prepared him for deadline day. It remains the most chaotic, opportunistic and unruly day in the football calendar. There will be deals to be done – big ones at that – yet it will be on Boehly and, to a lesser extent Thomas Tuchel to remain calm and not make a costly mistake.
The business concluded by Chelsea so far has been impressive, even if the process of identifying and pursuing talent has been slapdash at times. Raheem Sterling was first to arrive from Man City for £47.5million, and Kalidou Koulibaly followed from Napoli in a transfer worth £34m.
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Several players were then recruited for the Development Squad, and younger stars, such as Gabriel Slonina and Carney Chukwuemekawere, were brought in for no little expense. They were later joined by Cesare Casadei, who arrived from Inter Milan.
At first-team level, Chelsea went on to commit to a deal worth up to £62.5m for Marc Cucurella. That has been followed this week by the Blues finally bringing Wesley Fofana to the club from Leicester City for a fee understood to be around £70m without add-ons.
Despite all the spending, which is currently in excess of £250m, Chelsea are not done as we reach the final hours of the transfer window. At least one further incoming is expected, while Boehly is likely to sanction several exits as the Blues look to trim down their wage bill.
The likes of Kenedy and Michy Batshuayi – both of whom have continued to train with the first team when possible – are free to depart should they receive an acceptable offer. If that doesn't happen before the 11pm deadline, Chelsea may be prepared to come to an agreement over the final year of their respective contracts, as they did with Ross Barkley on Monday.
Marcos Alonso, meanwhile, is still hoping to seal a move to Barcelona; the Spaniard hasn't featured for Chelsea this season and has spent much of the campaign training away from the first-team group. The Blues have tried to include Alonso in prolonged talks with Barcelona for Pierre-Emerick Aubameyang but no agreement has been reached at the time of writing..
Amid strong interest from several Serie A clubs, Ethan Ampadu is set to depart on loan and join Spezia, who will not have an option to buy. And negotiations with Brighton and Hove Albion are set to continue over a permanent departure for Billy Gilmour, although Boehly is likely to push for a buy-back clause to be inserted.
football.london understands Xavier Simons is set to join Hull City on loan while fellow academy graduate Joe Haigh will spend the remainder of the campaign with Derby County. They are unlikely to be the other two departures from the Development Squad.
It's unlikely Chelsea sanction any major departure on deadline day despite Christian Pulisic being keen on a move away in search of first-team football ahead of the World Cup and Ajax yet to fully abandon their interest in Hakim Ziyech as they attempt to bring in a wide player to replace Anthony, who joined Manchester United earlier this week for £80million.
As to who arrives at Chelsea in the coming hours, that's not exactly easy to call. The Blues want to strengthen in midfield after a difficult start to the campaign and are also looking to bolster their attacking options with a wide player and a more traditional forward.
The signing of Fofana has ensured Tuchel has strong defensive options – further additions are not needed for the here and now. Chelsea will, though, try to secure a deal for young centre-back Ronnie Edwards having had two offers rejected for the teenager so far.
The Blues have been in talks with RB Leipzig in the past 48 hours regarding a deal for Josko Gvardiol, but the Croatian centre-back wouldn't arrive at Stamford Bridge until next summer. Given that potential outcome, a deal doesn't have to be closed before tonight's 11pm deadline.
Central midfield has quickly become a problem position for Tuchel this season. N'Golo Kante is ruled out for another month; Mateo Kovacic is not 100% fit; Ruben Loftus-Cheek suffered a knock against Southampton; Conor Gallagher missed that game due to suspension.
Chelsea have long considered bringing Declan Rice back to Stamford Bridge from West Ham United, but no deal was feasible this summer. So other options are now being courted. A £43m bid for Ajax's Edson Alvarez was submitted yesterday, and the Mexican is understood to be ready to move to Stamford Bridge.
An alternative is Ibrahim Sangare of PSV Eindhoven. Chelsea considered an approach for the 24-year-old earlier in the summer but opted to enter the season with the midfield options already on their books. That has now changed.
It's in attack where Chelsea are anticipated to be particularly busy. Having sold Timo Werner and sanctioned loan departures for Romelu Lukaku and Callum Hudson-Odoi, Chelsea are one forward light. Aubameyang was viewed as a solution – and one endorsed by Tuchel – but the jaw injury sustained during an assault at his home last week complicated matters.
Discussions continued between the two clubs yesterday, and a deal is not off the table for the 33-year-old that includes Alonso. Chelsea have also explored the idea of taking Aubameyang on loan, which is not hugely appealing to Barcelona given their current financial situation.
Chelsea's interest, meanwhile, in Everton winger Anthony Gordon ended almost as quickly as it began. The Blues did submit an offer for the England Under-21 international, but it was swiftly rejected by the Toffees, who are set to offer Gordon a new and improved contract.
Wilfried Zaha has been pitched as an alternative option, and talks have been held with the Ivory Coast international's camp, but no official bid has been submitted. It's a similar story with AC Milan star Rafael Leao, who super agent Jorge Mendes has offered to the Blues.
Leao would not come cheap – any move for the Portugal international would have to start at around £90million – and there is the further complication of the money he still owes to Sporting for terminating his contract and joining Lille in the summer of 2018 after around 50 supporters invaded the club's training ground and threatened players.
Neymar has been mooted as a potential Chelsea target all summer but striking a deal with Paris Saint-Germain for the Brazilian star is near-impossible given the time constraints. Tuchel, meanwhile, has held firm thus far on his belief that Cristiano Ronaldo shouldn't be signed from Manchester United despite Boehly being offered the chance.
What's clear is that Chelsea are going to be busy – and that will give Boehly a true taste of what deadline day is all about. He will have to be ready. It's going to be a long day.
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