Chelsea's free transfer track record is in line with other top clubs'
Didier Drogba and Thiago Silva exemplify the best of Chelsea's free transfer business. The Blues handle these situations much the same as England's and Europe's top clubs.
Scratch a Chelsea database, find another Didier Drogba achievement or two. Drogba is the only player that Chelsea twice released on a free transfer and, since Chelsea signed him on a free between those two, he’s the only player in Chelsea history to be involved in three free transfers with the club.

Players have only a few years at the beginning and end of their careers in which a free transfer won’t raise an eyebrow. Letting Drogba leave on two free transfers were signs of appreciation and respect, not his market value (although not driving home the point of his declining market value through transfer fee negotiations is part of the appreciation and respect).
Clubs that can attract high level, late career players to sign on a free transfer have a certain cachet among such players. If all they wanted was one last paycheck and an easy transition into retirement, Major League Soccer is a short flight west. But if they believe they have one or two more good years left in them, and a contract extension just isn’t in the cards at their current club, they are going to look for a club that will not just give them their last few paychecks, but that will give them their last trophy or two. Especially if it’s a trophy that they need to complete the boxed set.
Despite Chelsea’s strong tendency to win at least one trophy each season - over the last 10 years it’s more likely to be a European trophy than a Premier League title, which should be doubly attractive - the Blues are not one of the first clubs to come up in the conversation of “Who might sign Aging Legend on a free when his contract expires?”
Nor do Chelsea have a reputation for snapping up the undervalued free agents who somehow are adrift on July 1.
Is this a matter of push or pull? Or, taking the step back, is it the case at all?
Over the last 18 years, Chelsea are right in the middle of the pack of the top nine clubs in England and Europe in terms of releasing and signing players for free.
Who are the top nine clubs? The ones who win trophies in competitive leagues or coast on a reputation of being one of the “big clubs” from past (long past) achievements: Chelsea, Manchester City, Manchester United (ahem), Liverpool, Arsenal (AHEM), Real Madrid, Barcelona, Bayern Munich and Juventus. Had Bayern Munich not won the Champions League in 2020 they would not have been on the list for the same reason that PSG is not on the list.
The Blues released 70 players and signed 21 players on free transfers since 2004, fifth-most out of nine in each category.
There’s not much to regret among the outgoing free Blues, especially considering the age of most of the recognizable players on that list. Alongside a handful of serial loanees are players over 30 who did not want the usual one-year-at-a-time contract pattern. While “What could we have done if we kept Michael Ballack for another year?” is a fun counter-factual, it’s really not one that ends in a rewrite of club history.
And while Chelsea sometimes has a reputation for dealing with their rivals in ways other large clubs don’t, they at least make those rivals pay.
The Blues have only lost four players to other clubs in our “top nine”: William Gallas (29) and Willian (32) to Arsenal, Joe Cole (29) to Liverpool and Antonio Rudiger (29) to Real Madrid.
Meanwhile, they signed Claudio Pizarro, Michael Ballack and Willy Caballero for free from other clubs in our nine.
Chelsea are towards the bottom with Arsenal (3), Manchester United (1) and Bayern Munich (0) for signing free transfers from other top clubs. Juventus (7) and Manchester City (6) lead the list, which is a bit ironic given how long it’s been since Juventus has won in Europe and, well, City in Europe. On the other side, the Blues are again right in the middle for the number of free-to-top-clubs players.
Then there’s the matter of what these players accomplish after arriving at or leaving Stamford Bridge on free transfers.
Claudio Pizarro only played one year at Chelsea before a series of loans, and that happened to be one of the Blues’ rare fallow years and pretty much the club’s worst ever year in terms of performance in finals. Caballero, on the other hand, won more trophies with Chelsea than with any of his previous clubs, including a Champions League and Europa League. Ballack won five trophies (seven, if you count the Community Shield), almost as many as he did with participation trophy hoarders Bayern Munich.
Neither Gallas, Willian nor Cole won any trophies after leaving Chelsea (unless we’re still counting the Community Shield on behalf of Willian and Arsenal). Antonio Rudiger will almost certainly ruin this particular clean sheet.
Thiago Silva is the model free transfer for clubs and players
Chelsea’s second-most recent free transfer should lead the recruiting pitch for trophy-hungry veteran internationals over age 32.
Thiago Silva has 5-7 of each of the four Parc des Princes participation medals known as the Ligue 1 title, French Cup, French League Cup and French Super Cup. He also has a Serie A title, Italian Super Cup and Brazilian Cup, plus a Copa America. But 15 years in Europe had not brought him a single European trophy. Playing for PSG will do that to you. He finished his second season at Chelsea with a Champions League win, then added the UEFA Super Cup and FIFA Club World Cup in his third.
Another aspect to Silva’s success that could help Chelsea’s reputation among older players is that Silva won the Champions League with his former Paris-Saint Germain coach, Thomas Tuchel. That goes a long way to bolstering the case that not winning the Champions League despite having a purpose-built, petrostate-funded super-squad is a PSG thing as much as it is a Manchester City thing.
Maybe that’s why they get to keep their owners.
The only thing the breeds resentment more than success is Chelsea’s success (more on that soon from my colleague Kevin). Perhaps at some point Chelsea’s success will attract free transfers as effectively as it attracts free riders.
More Chelsea free transfer fun facts:
Didier Drogba was one of seven players in Chelsea’s starting XI for the Champions League final against Bayern Munich in 2012 who left the club on free transfers. Between the July 2012 and July 2019, Bosingwa, Gary Cahill, Ashley Cole, Frank Lampard, Mikel Jon Obi, Salomon Kalou and Drogba all ran down their contracts. So did one of the two subs to come on against Munich, Florent Malouda.
One of the four starters from that game that Chelsea sold is one of the few players that Chelsea have bought and sold twice: David Luiz.
Leaving Chelsea on a free transfer apparently looks good on your CV. Jody Morris, Gianfranco Zola, Carlo Cudicini, Ashley Cole, Ross Turnbull and Frank Lampard all went on to work for the club in some capacity. Before long, we’ll add John Terry to that list.
Two other free transfers, Joe Cole and Ron Harris (well before the range of this article), appeared in our namesake video.
To review, how many times did Chelsea sign Didier Drogba on a free transfer? Let’s ask Pep Guardiola: