It's fair to say that there is a strong argument that Tottenham Hotspur didn’t merely sign Gareth Bale from Southampton in 2007, but that they quietly removed tens of millions from the south coast that the Saints would never see again.
The Welshman's story begins at Southampton, where his rise was rapid, eye-catching, and unmistakably special already. Breaking into the first-team at just 16, Bale looked nothing like a typical academy graduate. That said, it was not abundantly clear exactly what he would become.
In terms of his profile, he was already fearless, and athletically ahead of his years, with a fantastic engine. He also possessed a left foot that already hinted at something extraordinary. That came from his early reputation as a dead-ball specialist — scoring stunning free-kicks against the likes of Derby County and West Bromwich Albion.
That quickly marked him out as one of the most exciting young defenders in the Football League, with Bale initially operating as an attacking left-back. Many others may well develop from being a flying winger into a full-back later in their career, but Bale went the opposite route.
Gareth Bale's transfer from Southampton to Tottenham Hotspur
Southampton, to their credit, developed him brilliantly. Bale wasn’t just a talented youth; he was trusted and given responsibility for both club and country. He played regularly, improved technically, and showed signs of maturity beyond his age. By the time Spurs came calling, Bale had already become one of the brightest teenage prospects outside the Premier League’s elite.
And yet, Tottenham secured Bale for an initial fee of around £5 million, which could eventually rise to £10 million with add-ons. He wasn't the first nor the last high-profile export from St. Mary's, but he went on to become the most famous of the lot.
At the time, that figure seemed reasonable. Bale was young, raw, and still technically a left-back. But history has a habit of reframing transfer fees — and few deals look as one-sided in hindsight. Six years later, Tottenham sold Bale to Real Madrid for approximately £86 million, which was a then world-record fee.
The scale of that profit is staggering. Spurs turned Southampton's academy gem into a global superstar and pocketed the difference.
The key to Bale’s explosion at Spurs was his transformation physically and technically. Initially used as that explosive left-back, he gradually pushed higher up the pitch, where his attributes truly flourished.
His pace and power became devastating, his ball-carrying unstoppable — as seen against Inter Milan's Maicon on that famous night at San Siro — and his shooting also became more ruthlessly efficient. Bale evolved into an explosive and athletic left winger — and eventually something closer to an all-round inside forward — who combined elite athleticism with increasingly refined technique.
Tottenham deserve credit for facilitating that evolution. Under Harry Redknapp, Bale was increasingly liberated from defensive responsibility and encouraged to attack space. His physical development was spectacular; he became stronger, faster, and more resilient, capable of overpowering full-backs and regularly scoring from range with ease.
Southampton's Gareth Bale regret at Spurs transfer deal
The Saints did not benefit from Bale’s superstardom. They did not receive a sell-on windfall that matched his value, nor did they enjoy his peak years in red and white. Instead, they watched from afar as a player they had nurtured became one of the best and most famous footballers on the planet — while another club banked the reward.
In an alternative reality, Southampton might have built a team around Bale and his devastating and powerful left boot, retained him longer, or at least structured a deal that reflected his ceiling. He could have been a franchise player, a talisman during their rise, or a financial cornerstone upon eventual sale. Instead, they got neither longevity nor legacy.
Of course, Southampton fans and club alike can — and should — feel proud. Bale’s journey began with them. His foundation was built at St Mary’s. But pride does not replace what was lost from their pockets.
Tottenham didn’t just sign Bale, they took his future value and benefited from a world-record sale. And Southampton, for all their excellent development work, were left watching millions disappear from their pockets. Sometimes, it benefits to hold out for more or a better deal. That is where they will have some regrets regarding Gareth Bale.