Arsène Wenger and Sir Alex Ferguson may not be soulmates but they share a key regret. Both men thought long and hard about signing the teenage Gareth Bale from Southampton but, ultimately, Wenger believed Arsenal could do without the Welshman while Ferguson suspected he was being asked to part with too much of Manchester United's money and said "no deal".
The then left-back ended up at Tottenham and, six years on, is the subject of a hitherto firmly resisted £86m bid from Real Madrid. If the price is deemed right by Daniel Levy, the Spurs chairman and a consummate negotiator, Bale, whose feet are itchy, would become the subject of the world's most expensive football transfer. Meanwhile Wenger and Ferguson can only rue their failure to second guess the 24-year-old's metamorphosis from full-back to left-winger to marauding attacking free spirit.
Should Bale move to Madrid, there is a school of thought it could trigger a chain of events concluding with Cristiano Ronaldo returning to Old Trafford and offering Ferguson's successor, David Moyes, a peerless "welcome" present. Wenger, though, has no such consolation in sight.
"I must confess it was a huge mistake not to sign Bale when we brought Theo Walcott from Southampton," said Arsenal's manager earlier this year. "We didn't take him because we didn't need another left-back but we could have played him in midfield. Gareth Bale struggled at the start at Tottenham but then they moved him to midfield. The careers of players are sometimes dependent on them being played in their right positions."
Ferguson proved suitably impressed but even he did not predict Bale's development from Walcott's shy, lanky, best friend at Southampton's academy into the 6ft 1in, supremely powerful, almost irresistibly pacy, technically accomplished, free-scoring athlete who would, one day, score a Champions League hat-trick against Internazionale. "Gareth Bale was a gifted, gangly boy," said Ferguson last season. "But, then, all of a sudden he was built like a light-heavyweight boxer."
By the time he destroyed Maicon at the San Siro in 2010, Bale had been converted to a left-winger by Harry Redknapp. Most importantly a rather slow-burn start at Spurs, in which indifferent form allied to two nasty injuries saw the then second-choice full-back close to being variously offloaded to Birmingham and Nottingham Forest for around £3m, was largely forgotten.
For a time, though, Bale's horizon had seemed bleak. In December 2007 complicated ankle surgery necessitated the insertion of a metal plate which has since been removed. The Welshman was sidelined for eight months and his career labelled under threat.
Another operation, to repair knee ligament damage this time, in 2009 represented less of a threat to his future but still disrupted progress. Moreover, much as Redknapp admired the teetotal youngster's dedication and recognised the many qualities – humility foremost among them – instilled by Bale's parents, he suspected him of being a little "soft".
These days Bale is a comfortable, confident interviewee and public speaker, not to mention an assured dressing room presence at the heart of the sharpest repartee, but back then he appeared rather less robust. At one point Redknapp even told him off for his habit – probably stemming more from anxiety and insecurity than vanity – of constantly fiddling with his hair and also complained that he limped off the training pitch "if he got a little mark".
Behind an apparently laid-back, good-humoured, exterior QPR's current manager can, on occasion, lacerate egos with well-timed caustic asides. Darren Bent is not the only player to have struggled to cope with the sharp side of Redknapp's tongue but Bale responded magnificently to "a kick up the arse", conceding: "I needed to toughen up."
George Burley, the manager who gave him his debut as a 16-year-old at Southampton, had initially feared for Bale. "I felt it was a bit of a gamble to go when he did," said Burley. "There's no doubt he struggled at first at Tottenham but I always believed he was a better prospect than Theo Walcott.
"Gareth has a fantastic ability with that magical left foot and he was great at free-kicks. As a left-back Championship teams marked him because he still dictated games. Manchester United wanted him but didn't offer enough."
Partly thanks to the decision of André Villas-Boas, the latest Spurs manager and a key mentor, to deploy his unique brand of speed and skill in a broad-brush "No10" type role, Bale's price tag has soared to the point where it looks eminently capable of putting the £80m Ronaldo's nose out of joint.
If fears that he, his girlfriend and their baby daughter may, like Michael Owen, struggle to settle in Madrid are probably unfounded, there are other concerns. The chances of his thriving in a self-esteem rich, highly political, Real dressing room possessing Ronaldo as its current kingpin certainly look daunting.
Bale remains undeterred. "I'm not afraid to leave the country," he has said. "I'd learn another language and grow as a person."
The bad news for Levy, Villas-Boas and every Spurs fan is that this does not seem an idle boast. "Bale is a strong personality," Juande Ramos, his manager at Tottenham, said. "He would adapt perfectly to life abroad."
• This article was amended on 29 July 2013. An earlier version said that Juande Ramos, rather than Martin Jol, was Bale's first manager at Tottenham.