Chelsea have been one of the biggest spenders in the Premier League since Todd Boehly took over the club in 2022
04:30, 08 Jul 2026
The players of Chelsea show their appreciation to Thiago Silva of Chelsea as they lift him at full-time following his final appearance in the team's victory i the Premier League match between Chelsea FC and AFC Bournemouth at Stamford Bridge on May 19, 2024 in London, England.
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Chelsea could be eyeing the free agency market this summer(Image: Ryan Pierse/Getty Images)
Chelsea have never been shy about flashing the cash in the transfer window.
The Blues were synonymous with waving the chequebook about during the Roman Abramovich era, and that has continued under BlueCo and Todd Boehly. The new ownership group spent approximately £1.5billion on transfer moves as of last summer, and that has only continued in 2026 following the acquisitions of Marco Palestra from Atalanta and Emmanuel Emegha from Strasbourg.
Xabi Alonso is the man now charged with knitting it all together on the pitch. He has become the fourth manager to take charge since January and will have his work cut out improving on previous acquisitions. During the 2025 window, Enzo Maresca signed Liam Delap, Dario Essugo, Estevao Willian, Jamie Gittens, Jorrel Hato and Joao Pedro - spending a total of £296.5m.
More spending is likely to take place, although it's not the only way the Blues have built squads in the past. Here, we take a look at three free agent signings to have come through the doors at Stamford Bridge.
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Ruud Gullit
Ruud Gullit.
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Ruud Gullit had an interesting impact at Chelsea(Image: Allsport UK /Allsport)
Chelsea welcomed a Ballon d'Or winner in the shape of Gullit, who had seen plenty of domestic success with the likes of Feyenoord, PSV and AC Milan. Gullit joined the Blues on a free transfer from Sampdoria and brought an air of experience and flair as he also led the Netherlands to the Euro 1988 title as captain.
His peak came in Italy, where he won the Serie A title three times and two European titles in 1989 and 1990. Gullit's time focusing solely on the midfield lasted just one year at Stamford Bridge, as he transitioned into a player-manager following Glenn Hoddle's departure to become England boss.
The Dutch star broke Chelsea's trophy drought by leading them to an FA Cup victory in 1997, marking their first piece of silverware in 26 years. He made 64 appearances and scored seven goals, winning the League Cup one year later and then departing London for Newcastle to become their new boss.
Despite his time at Chelsea ending on a sour note, Gullit has a positive outlook on his time at the club. He said: "I felt that living in England enriched my experiences in life, and enhanced my ideas about football. I still feel the same way.
"I am very proud I was there at the start for Chelsea, and to see what the Premier League has become too. Both have moved on so much, they are unrecognisable. But they had to start somewhere."
Thiago Silva
Thiago Silva.
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Thiago Silva won the Champions League with the Blues(Image: Darren Walsh/Chelsea FC via Getty Images)
Thiago Silva was a long-serving free agent for the Blues, initially signing in 2020 and spending four seasons at Stamford Bridge. Frank Lampard snapped up the experienced defender for free from Paris Saint-Germain.
The Brazilian had been successful domestically at PSG and AC Milan but had never lifted the Champions League with either club. However, he achieved his dream in his debut campaign with the Blues, winning the European trophy under Thomas Tuchel.
Silva spent three more years at Chelsea, making 155 appearances and becoming the first defender since John Terry in 2006 to win the Player of the Year award in 2023. He rejoined Fluminense in 2024, then headed to Porto to lift the league title, before returning to Brazil earlier this summer.
Winston Bogarde
Winston Bogarde.
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Winston Bogarde made just 12 appearances for the Blues(Image: Ben Radford /Allsport)
Winston Bogarde is looked upon as one of Chelsea's biggest free agent flops after he failed to impress in Spain and England following a Champions League win with Ajax. He was mentored by Louis van Gaal in the Netherlands and the boss brought him to Barcelona in 1998.
However, injuries and Van Gaal's diminishing influence meant that Bogarde was seeking other opportunities due to his struggles in the Barca defence. He joined the Blues in 2000, with Gianluca Vialli signing him just a week before he was sacked.
Bogarde failed to make an impact during four barren years at Stamford Bridge. He made just 12 appearances, clocking up 548 minutes and claiming that Chelsea's financial issues stopped him from forcing a loan move or transfer.
Speaking to The Guardian in 2015, he said: "Vialli bought me and when I had been there a week he got sacked. You have to look who the new manager’s going to be and if you’re still going to get a chance.
"They had to cut costs. My situation was not very good and we tried to solve it many ways. Like to maybe go on loan or sell me, or whatever. But in the end it didn’t work out."
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