Trent Alexander-Arnold will reportedly leave Liverpool for Real Madrid when his contract expires at the end of the season. As you can imagine, the Anfield faithful have reacted in a completely normal way and they wish their academy graduate – who has won everything with them – nothing but the best.
There have been some huge players walk on a Bosman over the years and Alexander-Arnold would arguably be the biggest ever to depart a Premier League club. If he does indeed join Los Blancos, he would certainly replace a former teammate as the biggest in the Reds’ Premier League history.
We have picked the biggest free transfer exit for each of the 20 Premier League sides.
Arsenal: Aaron Ramsey
If we did not restrict it to Bosman transfers, there would be a plethora of options for Arsenal. Mesut Ozil, ex-captain Pierre-Emerick Aubameyang and club-record signing at the time Nicolas Pepe all had their contracts terminated, but did not leave on a Jean-Marc.
Ramsey leaving was disappointing but nobody could blame him; the wages Juventus offered him were extraordinary and only a fool would have said no, especially taking into account it is a huge European club he was joining. It’s a shame it didn’t work a hero in two FA Cup finals.
Aston Villa: Thomas Hitzlsperger
Ron Vlaar, Brad Friedel, Nigel Reo-Coker and Mark Bosnich were all considered but a wise man once told me, ‘If in doubt, go for Der Hammer’.
The midfielder returned to Germany with Stuttgart following the expiry of his Villa contract in 2005. He did come back to England, signing for West Ham in July 2010 and spending the majority of 2012/13 at Everton.
Bournemouth: Jefferson Lerma
Lloyd Kelly might have prevailed through recency bias but Lerma’s departure was hardly ideal for Bournemouth in their preparation for returning to the top flight.
He was a linchpin in the Cherries midfield and has been an inspirational free transfer signing for Crystal Palace.
MORE: Every Premier League club’s best free transfer signing EVER
Brentford: Christian Eriksen
It doesn’t matter that there are barely any options for Brentford because Eriksen is the clear winner.
The ex-Tottenham Hotspur playmaker had to leave Serie A after his cardiac arrest at Euro 2020 and Brentford offered him a return to the Premier League, which was perfect in every way. The large Danish contingent would have helped Eriksen settle back into a competitive setting and the Bees were nowhere near bad enough for Eriksen to snub them and not good enough for there to be any chance of making him look out of his depth.
Despite wanting to keep him beyond the six-month contract he signed in January 2022, Brentford could not convince Eriksen to sign and the midfielder went to Manchester United.
Brighton: Jose Izquierdo
Enock Mwepu obviously does not count but is worth a mention considering the horrendous circumstances that ended his career while at Brighton.
Albion were a tricky one but we are pretty content with Izquierdo’s inclusion. What a throwback that is, by the way.
Davy Propper was originally our first choice but no Bosman means no inclusion. It threw a spanner in the works when it became clear he was still under contract when he left.
Chelsea: Antonio Rudiger
Thiago Silva, Andreas Christensen, Willian, Joe Cole, Michael Ballack, N’Golo Kante, Hernan Crespo, Nicolas Anelka, Andriy Shevchenko… Chelsea are comfortably the club with the most options.
Losing a prime Antonio Rudiger would have stung though. The German centre-back spent five years at Stamford Bridge before being snapped up by Real Madrid for nothing.
Crystal Palace: Wilfried Zaha
No contest here. Zaha is Palace’s greatest player of all time. He left when his contract expired in the summer of 2023, joining Turkish giants Galatasaray in an ambitious move for Champions League football.
After years of transfer stories linking him with a move to Arsenal, Zaha could not shine in Turkey and was loaned out to French side Lyon after a season. That did not go to plan either and he is now playing under Dean Smith for Charlotte FC in MLS.
Everton: Wayne Rooney
Obviously not the first time because that was for a transfer fee, but the second time Rooney left Everton is probably their most significant Bosman loss of the Premier League era.
Rooney scored an impressive ten goals in 30 league matches in 2017/18. Not only was his Goodison Park exit felt, but his arrival in the United States to play for D.C. United was as well. He would later go on to manage the MLS side for 453 days.
Fulham: Tosin Adarabioyo
Fulham screwed the pooch by letting Moussa Dembele join Celtic but that is more of a regret than a big transfer. Tosin Adarabioyo left the Cottagers for west London rivals Chelsea last summer in his prime years. It was gutting for Marco Silva but they have done just fine with Joachim Andersen returning as his replacement.
Ipswich: Sylvain Legwinski
It was always going to be difficult to find someone Ipswich regretfully released while they were a Premier League club and it turns out there was literally nobody worth mentioning. As a result, we have copped out and picked the player with the highest market value on Transfermarkt to leave the Tractor Boys for nothing. That man is Sylvain Legwinski, who departed after the 2007/08 campaign and did not find a club until the following April before spending a few months at St. Neots Town.
Leicester: Youri Tielemans
Caglar Soyuncu was an unfortunate loss but nothing comes close to Tielemans’ exit at the end of the 2022/23 campaign.
The Belgian left as a club legend after his FA Cup final winner in 2021. He was linked with Arsenal for bloody ages but ended up joining Aston Villa. After a difficult first year under Unai Emery, Tielemans is back to being one of the best midfielders in the Premier League.
Liverpool: Gini Wijnaldum
Emre Can certainly came to mind, especially as a younger player, but we think Liverpool lost more when Wijnaldum for Paris Saint-Germain in a 2021 summer transfer window that also included the signings of Lionel Messi, Gianluigi Donnarumma and Sergio Ramos. It is no surprise Wijnaldum’s arrival was overlooked.
The Dutch midfielder is now 34 and living the life in Saudi Arabia.
Manchester City: Ilkay Gundogan
Apologies for snubbing Sergio Aguero and Pep Guardiola’s ‘we cannoh replace him’ crocodile tears, but Gundogan is an easy choice. Alongside Erling Haaland, he was probably City’s most important player in their Treble-winning 2022/23 campaign, with his last job as City captain being to lift the Champions League trophy.
The German returned after a year at Barcelona but he isn’t as good anymore. We thought he would be fantastic as well…
In terms of successful free transfer signings, James Milner’s move from City to Liverpool is certainly up there, but that is not what we are looking at so I will shut up.
Manchester United: Paul Pogba
The difficult years that followed Peter Schmeichel’s departure in 1999 make him worth an honourable mention at least, but the fact Pogba left on a free transfer twice shades it for him.
Pogba’s time at Manchester United was riddled with discourse. On His Day, he was a world beater. Unfortunately for the Red Devils, he was pretty much only ever On His Day for France.
The best part of it all is obviously that Man United let Pogba join Juventus for nothing in 2012, re-signed him for a world-record £89million four years later, then let him join Juventus for nothing AGAIN in 2022.
United giving him a fat new contract and then losing him to that doping ban might have been overkill, even for them.
READ MORE: Antony, Sancho, Di Maria bottom five: Ranking all 65 Man Utd signings since Sir Alex retired in 2013
Newcastle: Jonas Gutierrez
Gutierrez’s exit in 2015 was emblematic of what Newcastle were under Mike Ashley’s ownership. The Argentine kept the Magpies in the Premier League after returning to the team following a bout with cancer and ended up being released over the phone by John Carver.
“John Carver rang me and told me the club weren’t going to offer me a new deal,” Ryan Taylor said at the time. “Then he asked me to pass the phone to Jonas, which was unbelievable… I can’t really blame John because he’s under instructions on what to do.”
Classy.
Nottingham Forest: Stuart Pearce
Despite all the fuss surrounding his arrival, Jesse Lingard was nowhere near good enough to be Forest’s pick, was he?
Psycho was a fair bit older than Lingard but desperate times lead to desperate measures. After spending 12 years at the club, Pearce walked on a Bosman in 1997.
It was a difficult final season for Pearce, who assumed caretaker player-manager duty following Frank Clark’s resignation. The role was eventually shared with Dave Bassett but Forest went down and a 35-year-old Pearce wanted out, joining Newcastle United.
Southampton: Stuart Armstrong
We got a bit stuck. This always happens with our one-per-club features.
Tottenham Hotspur: Sol Campbell
The most famous free transfer in Premier League history. Your Fabrizio Romanos of today would have got in there before Big Sol could rock up for a press conference announcing his astonishing transfer from Spurs to Arsenal in 2001, which left everyone and their nan absolutely shook.
Campbell had previously told fans he was staying but turned down the chance to become Spurs’ highest-paid player to fulfil his dream of playing in the Champions League. There was nothing to indicate Arsenal were even in contention for his signature but stunned journalists witnessed the sensational and iconic unveiling.
Campbell became an Arsenal Invincible and legend, while he remains a ‘Judas’ in the white half of north London.
MORE: Top ten greatest Premier League free transfers ever: Liverpool dominate and Zlatan scrapes in
West Ham: Ben Johnson
It is surprising how rubbish the options for West Ham are. If you have any better suggestions, we are all for hearing them.
Our logic is simple: London lad, been at the club since the age of seven, but most importantly in modern times, was someone the Hammers could have sold for pure profit. Opportunity. Missed.
Wolves: Adama Traore
Adama’s future was a talking point for bloody ages. Spurs were in the mix for a while and many anticipated a move to a big club when his Wolves contract expired in 2023. Alas, he signed for Fulham.
Wolves could have secured a decent fee for the Spanish winger and were gutted to lose him for nothing.
