Despite having a squad full of great players such as Moisés Caicedo, Cole Palmer and Marc Cucurella, Chelsea have signed more than their fair share of unlucky players in recent years.
For example, Axel Disasi, Pierre-Emerick Aubameyang, Joao Felix and Mykhailo Mudryk are just some of the club’s worst pickups since ownership took over.
But when it comes to the most notable example of a failed signing at Stamford Bridge, many fans and pundits alike will point to Raheem Sterling.
Unfortunately for Chelsea, one of Enzo Maresca’s latest signings looks set to follow a similar path to the Englishman.
Sterling’s Chelsea career
When Chelsea initially signed Sterling for around £50 million in the summer of 2022, there was understandably considerable excitement from fans and pundits.
After all, here was a player who won the Premier League four times during his time at Manchester City, racking up 131 goals and 86 assists in 339 games.
The positive feelings about this deal lasted quite a while, and the British began life in the capital quite successfully, even if he did not have electricity.
For example, he had three goals and one assist in his first five league games, and contributed eight goals in 19 games by the end of the year.
He would end his first season with a respectable nine goals and four assists in 38 games.
Interestingly, in terms of actual results, the next season was even better, finishing the season having been involved in 21 goals in 43 matches.
However, the club appointed Maresca in the summer and the Italian manager decided he no longer wanted to use the former City star, so a loan move to Arsenal was agreed.
The winger’s time in North London was nothing short of a disaster.
Described as a “passenger” by Arsenal writer Charles Watts, the Kingston-born ace appeared to have lost all of his dynamism, finishing the season with just one goal and five assists in 28 games.
Sterling’s Arsenal record | ||||
|---|---|---|---|---|
competition | EPL | UCL | FA Cup | EFL Cup |
Appearance | 12 | 6 | 1 | 4 |
minutes | 307 minutes | 297′ | 80 minutes | 270′ |
the goal | 0 | 0 | 0 | 1 |
assist | 1 | 2 | 0 | 1 |
Number of goals involved per match | 0.08 | 0.33 | 0.00 | 0.50 |
Hours per goal involvement | 307 minutes | 148.5 feet | Not applicable | 135 minutes |
All stats via Transfermarkt | ||||
Since returning to west London, the former England international has been demoted to the club’s ‘bomb squad’ and is unlikely to feature for Chelsea again.
Overall, despite some quality moments here and there, it would be hard to describe Sterling’s move to Chelsea as anything other than a dud, and the bad news is that the current squad could end up being an even bigger failure over time.
Chelsea’s bad players who could fail even more than Sterling
Unfortunately, some of Chelsea’s summer signings have so far disappointed, including Liam Delap and Jorrell Hato.
But when it comes to players who could end up being bigger failures than Sterling, it’s impossible to ignore Jamie Gittens.
Like his compatriot, the dynamic winger’s signing was met with considerable excitement, and rightly so.
For example, in 49 matches for Borussia Dortmund last season, the Reading-born dynamo was involved in 17 goals.
The 21-year-old has also scored against Bayern Munich in the league and away to Real Madrid in the Champions League, with Sky Sports’ Dougie Critchley at one point describing him as “England’s best left winger”.
As such, there was a certain expectation that he would be a very useful option from the left for Maresca and the team, even if he was not meant to be a genuine star from the start.
Unfortunately, that hasn’t happened yet.
In fact, the summer signing appeared to be way off pace, struggling in nearly every tournament he played.
For example, in the League Cup, he played well against Cardiff City in League One, with substitute Alejandro Garnacho scoring two goals.
In total, the Englishman has made 20 appearances for the Blues, scoring one goal and providing five assists, three of which came in the League Cup and the other three in league matches against relegation-threatened teams.
Given this poor return, poor performance and the fact that he could fall further down the pecking order now that the club is interested in Antoine Semenyo, it would be hard to agree with one analyst that the winger was a “pointless signing”.
Gittens’ recent league results | ||
|---|---|---|
season | 24/25 | 25/26 |
Appearance | 32 | 12 |
minutes | 1784 | 426 minutes |
the goal | 8 | 0 |
assist | 4 | 2 |
Number of goals involved per match | 0.37 | 0.16 |
Hours per goal involvement | 148.66 feet | 213 minutes |
All stats via Transfermarkt | ||
Additionally, it’s easy to imagine him becoming another Sterling-like figure on the team, but perhaps the only reason he hasn’t been seen that way yet is the fact that he’s a new signing and doesn’t make as much money.
At the end of the day, Gittens is a talented player who still has time to develop, but as it stands, it looks like a deal with Chelsea has fallen through.
Chelsea considering £47m move to sign new Moises Caicedo in January
The incredible prospect could develop into another Caicedo for Chelsea and Maresca.

