It all went a bit pear-shaped after Chelsea conquered Europe for the second time, with Todd Boehly's scattergun spending strategy yielding rotten results until signs of stability surfaced last year, under Mauricio Pochettino.
Now, with Enzo Maresca at the wheel, the Blues are thriving as one of the Premier League's standout sides. It's never a given, but it'd be a brave fan to bet against Chelsea lifting the Conference League trophy in May 2025.
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It's all coming together, a confluence of individual parts that have finally, finally, restored Chelsea to a position of genuine strength among Europe's elite outfits.
We talk about the high-priced deals that the new regime have engineered, but what about the shrewder signings under American ownership?
Todd Boehly's shrewdest Chelsea signings
You can't really call the £42.5m deal to bring Cole Palmer to Stamford Bridge shrewd, but Chelsea's scouts saw something that was worth forking out such a sum on a largely untested prospect, even though his high quality was clear.
The decision to sign Jadon Sancho on loan this summer was also a well-built deal, with the hitherto struggling winger completing a season-long loan move with the option for a sharp £25m permanent fee.
Elsewhere, the £12m Renato Veiga, 21, looks like a real talent in Chelsea's Conference League squad, leaving Basel for the west London project this year and being praised as a "hidden gem" by analyst Ben Mattinson.
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Then, of course, this week's man of the moment: Marc Guiu. The 18-year-old, purchased from Barcelona for only £5m in July, bagged a hat-trick against Shamrock Rovers on Thursday and looks to be a high-class striking in the making, indeed perched as the Conference League's top scorer this season.
He's perhaps the finest teenage forward in Chelsea's ranks right now, and that £5m figure might come to look like the shrewdest deal of them all in a few years time.
However, one of the Blues stars this season was actually welcomed for even less. Tosin Adarabioyo is starting to prove that he's one of Chelsea's most fundamental parts.
Chelsea have hit the jackpot on Tosin Adarabioyo
Like Palmer, Tosin emerged from Man City's youth system, though he completed a string of loan moves and then signed for Fulham before finding a home at Stamford Bridge.
Tosin - Career Stats by Club
Club
Fulham
West Brom
Blackburn
Chelsea
Man City
Stats via Transfermarkt
The 27-year-old centre-back signed on a free transfer in July after his Cottagers contract expired, and though he's not yet been a mainstay in the Premier League, Tosin has completed two of the past three top-flight matches.
While the bulk of Tosin's Chelsea career so far has been played out on the continental stage, there's a noticeable shift toward the ostensibly superior Premier League squad, and given that he didn't play against Shamrock, it would seem that Maresca is gearing up to start him once again at Everton this weekend.
Tosin
He has everything and more to become a nailed-down starter, ranking among the top 1% of defenders in the Conference League this year for passes attempted and pass completion, the top 7% for shot-creating actions and the top 20% for progressive passes per 90, as per FBref.
A pass is considered progressive if the distance between the starting point and the next touch is at least 10 meters closer to the opponent's goal or any completed pass into the penalty area.
It's made all the more impressive by his £120k-per-week salary, which is by no means a pittance but not all that exorbitant for a player joining an affluent club such as Chelsea on a free transfer.
As per Transfermarkt, the titan's market value has already shot up to about £17m too, so even if he doesn't fit into the club's long-term vision, a tidy profit is sure to be turned.
Not that that eventuality will be in the pipeline any time soon, since Tosin has been described as "one of the leaders in the dressing room" by Maresca, who continued to reveal that he has been "delighted" with the new recruit's progress.
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This makes a telling comment on Tosin's demeanour, tenacity and leadership qualities, something that is vital if the second-placed Premier League side are to remain in contention for an unlikely title triumph.
Those of a Chelsea persuasion have been understandably coy when quizzed on the excellent position that they have forged at this festive stage, but the plain truth is that it is a real possibility for this talented bunch, for Liverpool have shown themselves to be flawed in instances this season and Arsenal and Manchester City are dropping shedloads of points.
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Maresca, for sure, has been coy on the subject - and why wouldn't he? However, the Italian coach's seeming decision to bring Tosin into Premier League contention on a regular basis bespeaks his thought process in placing the central defender on a higher rung on Chelsea's ladder.
Tosin is a leader and a "special player" - as has been said by Fulham boss Marco Silva - and his communication and spirit will be crucial in keeping the squad together as a whole across the coming months.
After several years of suffering, Chelsea should afford themselves that belief that great things might be achieved this year. Tosin is definitely not the flashiest player in Maresca's first team, but his leadership ability might prove to be the difference-maker as the business end starts to draw nearer and nearer.
Luckily for him, he's also a wonderful player, and very much in contention for the mantle of Chelsea's shrewdest signing of the Boehly era.
nicolas-jackson-chelsea-premier-league Related
[Outscoring Guiu & Jackson: Chelsea pushing to sign "new Aguero" for £25m](https://www.footballfancast.com/chelsea-interested-in-signing-new-aguero-manfred-ugalde-from-spartak-moscow/ "Outscoring Guiu & Jackson: Chelsea pushing to sign "new Aguero" for £25m")
Chelsea are interested in the 'new Aguero' who is currently outscoring Jackson and Guiu