The summer transfer window of 2017 remains the most infamous of the Roman Abramovich era. It's not only the deals that Chelsea completed – Alvaro Morata, Tiemoue Bakayoko, Danny Drinkwater and Davide Zappacosta to name four – but it's also because of the moves the Blues failed to get over the line.
Fernando Llorente and Alex Oxlade-Chamberlain were wanted by Antonio Conte during the window. Neither arrived. The big one, however, was Romelu Lukaku, who spurned Chelsea's advances in favour of joining Manchester United from Everton.
It's often forgotten that the Blues also failed in their attempts to bring in a midfielder from the Toffees, that a £35million deadline day deal collapsed in the final hours of the window.
That's almost certainly because Chelsea revived their interest in January. On that occasion, the transfer was completed. And for a fraction of the price: Ross Barkley joined for £15million.
"I'm overwhelmed, I'm looking forward to it and I'm really excited to get started," Barkley told Chelsea's official website. "To be given a fresh start at a new club like Chelsea, it's unbelievable for me."
There was a belief that Barkley's development had stalled at Everton and that the challenge of playing for a side that was competing at the top of the Premier League would unlock his true potential. He was handed the No. 8 shirt previously held by Frank Lampard, the hope being he could emulate the Chelsea legend.
Barkley's first six months weren't easy as he struggled with injury. His first full campaign, meanwhile, saw him job-share a midfield role with Mateo Kovacic under Maurizio Sarri.
It was the man whose shirt he wore – Lampard – who got the best out of Barkley. Flashes of ability were extrapolated to 90-minute performances. But just as it appeared as though everything was falling into place for the England international, the Covid pandemic hit and his momentum was halted.
On football's return, Barkley was pushed to the periphery. It was no surprise he ended up joining Aston Villa for the 2020/21 campaign, although that did not go as hoped and he returned to Chelsea in the summer.
In a move that appeared to signal Barkley's career at Stamford Bridge was over, the No. 8 shirt was taken off him and handed to Mateo Kovacic. And had a club approached Chelsea for the midfielder with a reasonable bid, he would've departed.
That didn't happen and suddenly Barkley was back in the first-team fold. He has gone on to make 12 appearances under Thomas Tuchel, but only four of those have been starts.
His last appearance came from the substitutes' bench against Chesterfield in the FA Cup – the midfielder was handed 24 minutes in what was a comfortable win. More tellingly, his last Premier League outing came on December 16 against Everton.
A Chelsea exit, almost certainly on loan, has been a possibility this month. Tuchel even admitted as much ahead of the Chesterfield clash.
“We haven’t discussed it yet [a loan deal]. It depends what Ross wants, what possibilities there are, and what makes sense. Let’s see.
"There’s always a chance to make it onto the pitch, especially with a lot of Covid and injury cases. The situation has not changed, not for Ross, not for anybody else.”
Barkley was given minutes by Tuchel during a period in which Chelsea's attack was threadbare. It's no great surprise his action has been limited, with Romelu Lukaku, Kai Havertz, Timo Werner, Christian Pulisic, Hakim Ziyech, Callum Hudson-Odoi and Mason Mount all fit.
At 28 years old, Barkley is in the prime of his career. He is an effective ball-carrier and has a range of passing that can turn a match – Chelsea supporters witnessed that earlier this season against Southampton. He should be far more than a squad option, a player who may - if he is lucky - make the bench.
Unfortunately for both Barkley and Chelsea, background interest hasn't resulted in any firm bid being made. That could change, of course, as the transfer deadline approaches. Then a decision would be required.
Barkley needs to get out of Stamford Bridge one way or another. His career, one that burnt so bright in its early stages, is in genuine danger of fizzling out.
There also seems little point in Chelsea keeping Barkley just for the sake of it; that he featured against Chesterfield ahead of the highly-rated Charlie Webster, for instance, was potentially damaging, given the 17-year-old's pro deal expires at the end of next season.
The transfer mistakes made by the Blues during that 2017 window continue to prove costly. And by not cutting their losses, Chelsea have only amplified them. It's time to break that pattern and it starts with Barkley.