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'Southgate turned down my UCL-winning client - Man Utd bought him for £27m instead'


  • In the mid 2000s, Gareth Southgate had the chance to sign Nani from Sporting Lisbon.
  • After turning him down, Nani joined Manchester United where he went onto to win the Premier League & Champions League.
  • During his time at United, Middlesbrough were relegated under Southgate and have only played one season back in the top flight since.

Hindsight can be both good and bad. On the plus side, lessons can be learned and future negative events can be avoided. On the other side of the coin, it can be equally horrible. Football managers and agents alike know that feeling all too well, as this story from an interview with former player and football agent Barry Silkman reflects.

Read on, as GIVEMESPORT recounts the time Gareth Southgate, now England manager, passed up the opportunity to sign exciting Portuguese winger Nani while in charge at Middlesbrough - a decision that likely left him kicking himself as Nani's career at Manchester United went one way, Boro's fortunes almost immediately headed the other.

Nani's Early Career

Turning heads in Europe


Luis Carlos Almeida da Cunha, or as he's commonly known, Nani, emerged as yet another gem from Sporting Lisbon's academy in the early to mid 2000s. Following in the footsteps of eventual team-mate Cristiano Ronaldo, who is two years his senior, Luis lived through traumatic early years before letting his talents pave the way ahead.

Born in Portugal to a Cape Verdean father, his father left for the island when his son was five, and never returned. To make matters worse, Nani's mother also abandoned him when he was 12 - leaving for the Netherlands. Raised by his aunt, and taught how to play football by his older brother, it was clear he had a gift.

Nani joined Sporting CP from his first club, Real Massama. After two seasons in the youth team, where he won the National Junior Championship in 2004-05, Nani was promoted to the first team early in the 2005-06 season and immediately demonstrated a raw and agile technique - especially with on-ball skills and dribbling. He scored his first Sporting goal on 30 October 2005, opening the scoring in a 2–2 draw away to Boavista. Ultimately, he ended the season with five goals from 36 appearances in all competitions.

While, at this point, Nani (a nickname he fondly received from one of his sisters) looked to be Portuguese football's best kept secret, the next season blasted the trickster onto the wider European conscience. This was capped by an excellent Champions League performance against Spartak Moscow, a Taca de Portugal crown, and the award of blasted SJPF Young Player of the Month for May 2007. Thus, while the interests around Nani began to simmer and rise, this was where Barry Silkman steps in.

Southgate's Snub

Middlesbrough's pain was Manchester United's gain

Barry Silkman, a former player in the 1970s era of English football, had made his name as a hardworking midfielder, so it was no surprise that in post-career life, he put that work-rate into a job around football. As an agent, he earned a reputation as a fine talent hunter, and of course, Nani fell onto the experienced football man's radar.

In an interview with Sport, Silkman spoke of Nani as a player he regretted missing out on, explaining Southgate's mistake in letting the winger go elsewhere:

"I saw a player in Portugal a few years ago called Nani. I tried to do a deal with Middlesbrough who I was very close to at the time; I did a lot of deals when Steve McClaren was manager. I offered Nani to Middlesbrough and Gareth Southgate didn’t fancy him. He was £3.5 million. He went to Manchester United for £27 million, and it was only eight or nine months later, that’s all it was.

Manchester United’s chief executive, David Gill, actually phoned Middlesbrough chief executive Keith Lamb to ask him if that story was true! And Keith Lamb said 'yeah it is'. "

The rest, they say, is history - with Nani going to Manchester United for £27 million. As it is noticeable below, Nani had quite the career at United, and it makes you think why on earth Southgate didn't see the player's talents.

When Nani signed in the summer of 2007, it would be unheard of just how dramatic his and Southgate's paths would be, in all respects. In the 2007-08 term, Nani kicked on at United and began to steadily adapt to life in a different country before his best years ultimately arrived after two seasons.

Using that as a parameter, following that first season, Southgate's Middlesbrough finished 13th, before 2008-09 saw the Riverside club finish 19th and relegated. Nani had a Champions League winner's medal at this point. Southgate left his role as manager the next term before ultimately going into England's youth set-up and a steady ascent of his own, leaving this story with a pleasantly restored equilibrium.

Nani's Manchester United Career (All Competitions)







Best Scoring Season

2010-11 (10 goals)

Best Assisting Season

2010-11 (20 assists)


Premier League (x4), Football League Cup (x2), FA Community Shield (x4), UEFA Champions League (x1), FIFA Club World Cup (x1)


Portugal have an incredible amount of talented players - enough to make Cristiano Ronaldo miss out on the 10 most valuable assets the nation boasts.

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