Fernando Torres
It's still tricky to work out which club came off worse from the January 2011 deadline-day deal that saw Liverpool sell Torres to Chelsea for a British record £50 million, and then replace him with £35m Andy Carroll. Who was better value for money? Let's call it a draw. A goalless one.
Occasional impressions of a clinical goalscorer sometimes lulled pundits into rash declarations that Torres was 'getting back to his best' at Chelsea, only for the Spaniard to prove them wrong. Torres did help the Blues win the Champions League, famously scoring at the Nou Camp, so Roman Abramovich may still believe he was worth it.
But, shorn of the confidence that once helped him become an Anfield hero, Torres has netted only 20 goals in 110 league games for Chelsea and has finally been replaced for good by Diego Costa.
Robinho
"On the last day, Chelsea made a great proposal and I accepted," declared the Brazilian after making his £32.5m move from Real Madrid to the Premier League in 2008.
Just one slight problem. "You mean Manchester City?"
"Yes, Manchester, sorry."
There's nothing like getting off on the right foot at a new club. If Robinho appeared dazed and confused after signing for City on the manic deadline day that followed Sheikh Mansour's takeover, his head remained elsewhere for much of his time at Eastlands.
There were brief moments of genius that elevated him marginally above Jo in the list of City's worst Samba signings, but he also went AWOL and faced investigations over an alleged sexual assault before being cleared. He left two years later before missing out on selection for Brazil's own World Cup, which ended hopelessly.
Juan Sebastian Veron
"He is a f***ing great player. And you're all f***ing idiots."
On that note, Sir Alex Ferguson departed the press conference and ordered journalists to leave the training ground.
The Manchester United boss had become protective of his £28.1m record signing from Lazio, who was earning criticism for his performances at Old Trafford. The Argentine midfielder could play a sumptuous pass one minute and hammer a shot into the top tier the next, as he never found the consistency his talent promised.
Like Robinho, perhaps his heart was somewhere else; maybe even with the club that his uncle Pedro Verde represented. "I was hoping to play for Sheffield United and here I am at Manchester United!" Veron once joked.
Despite Ferguson's defence of Veron, he eventually conceded defeat and sold him to Chelsea for £15m – another move that the player failed to live up to. It could have been so different at Bramall Lane.
Alan Shearer
Shearer broke the British transfer record twice; first when he moved from Southampton to Blackburn Rovers for £3.6m in 1992, and then when he joined boyhood club Newcastle United for £15m shortly after Euro 96.
But before he left Rovers, the England striker received an extraordinary offer from their steel magnate owner Jack Walker – to become the club's manager, aged only 25.
Shearer politely declined the offer – mainly because of his desire to join Newcastle, but also to spend more time creosoting his fence (possibly), as he famously did to celebrate Blackburn's title win in 1995.
The England star chose Newcastle over Manchester United in 1996, having also held talks with the Old Trafford club, going on to score a Premier League record 260 goals in 434 appearances.
Duncan Ferguson
The most expensive player in Britain was north of the border in 1993 when Rangers paid £4m for a particularly fiery targetman from Dundee United.
Ferguson would score only two league goals for the Gers, with his time at Ibrox better remembered for headbutting Raith Rovers' Jock McStay. The striker was banned for 12 matches by the Scottish FA, charged with assault and swiftly moved on to Everton.
A year later he was found guilty of assaulting McStay and sentenced to three months at Barlinnie jail. Amusingly, Ferguson's incarceration was later referenced by the Finnish Radio Symphony Orchestra after Everton fan Osmo Tapio Raihala penned the composition 'Barlinnie Nine'. Of course you're going to listen to it (for about five seconds).
Ian Rush
When Liverpool called a press conference in 1988, few knew what would be announced until the familiar figure of Rush walked into the room.
Boss Kenny Dalglish had somehow kept the Welshman's £2.7m return from Juventus a secret, in the days before the internet and Sky Sports News.
Dalglish had been the British transfer record holder himself as a player when he joined Liverpool from Celtic for £440,000 in 1977, and would break the record several times as a manager. He paid £1.9m for Peter Beardsley at Anfield before swooping for both Alan Shearer and £5m Chris Sutton at Blackburn.
But despite being Britain's most expensive player, Rush had actually returned to Liverpool for less than what Juventus paid to take him to Italy a year earlier; his £3.2m move to Juventus delivered only seven goals in Serie A.
Trevor Francis
Some say that Francis didn't achieve his full potential after becoming the first £1m player in British transfer history in 1979.
After all, his contributions were limited to scoring the winning goal in the European Cup final, a trivial fixture of little importance.
Even Brian Clough seemed somewhat underwhelmed at the press conference unveiling Francis, since it was delaying him from a pre-arranged game of squash. The forward would last only two years at the City Ground before moving on to Manchester City.
But his goal against Malmo, delivering the first of Forest's two European Cups, would go down as one of the most memorable moments in English football.
Denis Law
Law broke the British record for a second time when he cut short a turbulent spell at Torino to join Manchester United for £115,000 in 1962.
The Scot had moved to Manchester City from Huddersfield for £55,000 two years earlier, before his ill-fated switch to Italy.
Law was injured in a car crash after his English team-mate Joe Baker drove the wrong way round a roundabout and flipped their vehicle. If that wasn't bad enough, his time at Torino took a bizarre turn when he was sent off in a match at the request of his own coach, who was said to have been riled by the temerity of the forward's decision to take a throw-in.
Law was due to sign for Manchester United but was then informed he was going to Juventus instead, so flew back to Scotland in protest. Eventually, he got his way.
Tommy Lawton
Lawton had long established himself as one of the greats of the British game when he signed for Third Division South side Notts County for £20,000 in 1947.
He had somehow been persuaded to join the Magpies by manager Arthur Stollery, his former physio at Chelsea, and lasted a little longer at Meadow Lane than Sol Campbell. Lawton scored 103 goals in five seasons as the club climbed into the Second Division, before finishing his career in the top flight with Arsenal.
In his younger days he had made notable guest appearances for various clubs, including playing two matches on Christmas Day in 1940; one for Everton and another for Tranmere Rovers.
Andy McCombie
Jack Colback, take note.
A full 110 years ago McCombie also made the controversial move from Sunderland to Newcastle United, for a British record fee of £700. But the Scottish full-back's switch was clouded in acrimony after a dispute with the Black Cats over £100 given to him to start a business.
McCombie regarded it as a gift rather than a loan, and when the club asked for it back he refused. An FA investigation sided with the player and found financial irregularities at the club, for which Sunderland were fined £250.
McCombie was soon sold to Newcastle but didn't enjoy a happy return to Sunderland, scoring an own goal within 60 seconds of a 3-1 defeat in his first match back at Roker Park.
