Football League World
·27. Juli 2025
Middlesbrough almost struck gold with £3.5m transfer deal – Portsmouth & Everton did instead

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·27. Juli 2025
Portsmouth and Everton saw the benefits of the impressive Sylvain Distin, and it will further frustrate Middlesbrough supporters.
Sylvain Distin was Manchester City’s Player of the Year and went on to become Everton’s Players’ Player of the Season, whilst also winning an FA Cup at Portsmouth on the way to becoming a cult hero with at least three English clubs – but Middlesbrough fans will believe he should have been one of their own fans’ favourites, too.
The French centre-back, who began his career in his home country with Joue-les-Tours, Tours, Guegnon and then a move to Paris Saint-Germain, first arrived in England in the summer of 2001.
He spent a season on loan at Newcastle United from PSG, before joining Manchester City on a permanent deal in the summer of 2002, following their promotion back to the top-flight in the previous campaign.
Distin was an instrumental part of the City side that managed to immediately re-establish themselves back in the Premier League, helping them finish ninth and being named their Player of the Year for that campaign, before eventually being named captain.
He went on to play every minute of each of the next two Premier League seasons, too, before again remaining a key man in the 2005/06 campaign.
In August 2006, it was believed to be the case that Middlesbrough were on the verge of signing Distin for an undisclosed fee, believed to be in the region of £3.5 million, having held talks with the ‘unsettled’ Frenchman.
However, despite the fact that he and Gareth Southgate had held talks, with the latter having even made plans to include him in ‘Boro’s eleven for their opening day clash against Reading at the Madejski Stadium, Stuart Pearce convinced him to remain in Manchester instead.
Middlesbrough had been a team regularly challenging towards the top-half of the table through the 2000s in the Premier League, reaching the UEFA Cup final and winning the League Cup during that decade.
The second-half of the decade saw them become fairly chaotic at the back, and that eventually led to their demise, so the pursuit of Distin wasn't necessarily ambitious, but highlighted their standing.
It was Southgate's first summer as a manager, and he instead brought in German defender Robert Huth from Chelsea, but he massively underwhelmed at the club and, due to injuries and form, made just 12 appearances that season.
His decision only lasted a year or so, as Distin eventually departed City in the summer of 2007 for Portsmouth, and the rest of his career, with Pompey and Everton, rubbed further salt into the wounds of Middlesbrough supporters.
Having joined Pompey on a free transfer at the end of his contract at the then City of Manchester Stadium, Distin immediately became a key man down at Fratton Park.
Having been named vice-captain by manager Harry Redknapp, Distin went on to make 95 appearances for the club in just over two seasons, often captaining the side due to injuries to Sol Campbell.
Distin was vice-captain but started alongside skipper Campbell in the final game of his first season at Pompey, which came in the FA Cup final at Wembley Stadium as they defeated Cardiff City by a goal to nil, courtesy of a 37th minute winner scored by Nwankwo Kanu.
Distin had been immense throughout Pompey’s cup run, and he remained a rock at the back in their second campaign, too, as they finished 14th in the table, with off-field issues then beginning to rear their head down on the south coast.
As matters began to get worse for the club in the summer transfer window of 2009, they decided and managed to cash in on the excellent service of Distin for a fee believed to be in the region of £5.3 million.
The club paying that fee was an Everton side who remained ambitiously striving to get back into the top four and the UEFA Champions League spots under the management of David Moyes.
At Goodison Park, Distin continued to establish himself as one of the very best centre-backs in the Premier League as he made over 200 appearances for the Toffees.
Having initially signed a three-year deal, Distin eventually signed a contract extension in the summer of 2012, a couple of months after having been named the Players’ Player of the Year.
His first few years at Everton saw him have almost entirely consistent highs in terms of his excellent and impressive performance level, albeit there were a couple of high-profile, albeit rare, gaffs, such as his red card against Sporting CP in the UEFA Europa League in 2010, as well as his misplaced pass to allow Luis Suárez to score in the FA Cup semi-final against Liverpool in 2012.
Overall, though, Distin had continued his success from his days at Manchester City and Portsmouth, and even went on to have something of an Indian summer to his Goodison Park career, too, with Roberto Martinez at the helm.
Perhaps not best known for his footwork, he actually became a fulcrum of the extremely entertaining Everton side that finished fifth in the 2013/14 campaign and that boasted the likes of Leighton Baines, Ross Barkley, Gerard Deulofeu and Romelu Lukaku.
He even remained in the Premier League for a season after leaving Everton, making 17 appearances across all competitions for an AFC Bournemouth side that had just been promoted to the Premier League.
At City, Portsmouth, Everton and, even perhaps Bournemouth and Newcastle, Distin is remembered extremely fondly and well by supporters for the impact and quality he had and showed.
There will be an immense frustration for ‘Boro fans that Southgate and the Smoggies weren’t able to eventually tempt him over to Teesside, especially as Middlesbrough found themselves relegated at the end of the 2008/09 campaign; the season after Distin lifted the FA Cup with Pompey and the summer in which he earned himself his move to the Toffees.
Cases of ‘what could have been’ are aplenty and common in football, and especially in the EFL, but Middlesbrough’s pursuit of Distin certainly ranks high for that category.
Middlesbrough supporters may well justly believe that had Southgate been able to convince Distin to move to the Riverside that summer, then their entire future could have been different.
The Frenchman went on to win silverware in the season 'Boro went down, and there will be a view that had he instead moved to Middlesbrough a year before his move to Portsmouth then not only would they have managed to steer clear from circling the drain and eventually going down in the top-flight, but they could have kicked on even further, having been UEFA Cup runners' up in the mid-2000s.
That isn't necessarily even short-sighted, either, with his continued excellence at Everton, and then proving to be a steady, experienced head at Bournemouth, means that Middlesbrough missed out on a centre-back who could realistically have been a key figure on Teesside for the next decade.