Glenn Moore: If Modric had gone to Bridge, Villas-Boas would still have a job

Luka Modric: The Croatian is under contract at Spurs until 2016 but could look elsewhere again (PA)

Luka Modric could be forgiven for running out at Stamford Bridge today, seeing the big screen advertising tickets for a Champions League quarter-final, and wondering what might have been. And if he does not, Andre Villas-Boas, should he interrupt his gardening to tune in on television, is bound to ponder the subject.

Last August, it seemed inevitable that the Croatian midfielder would move to Chelsea for around £40 million, not least because he seemed to be actively agitating to do so and Harry Redknapp appeared to be pondering how to spend the money. At one stage, Modric was left out of the Tottenham Hotspur team, then returned to be booed as Spurs rolled over 5-1 at home against Manchester City in a game Modric had unsuccessfully asked Redknapp to be omitted from.

Daniel Levy, however, was following a different script. The Tottenham chairman played hardball, not to drive the fee up, as when selling Michael Carrick, Dimitar Berbatov and Robbie Keane, bringing in around £70m, but because the player was under contract and Levy had no intention of selling. Giving in would broadcast the message that Spurs were still a selling club. Gareth Bale would soon follow and Spurs would revert to being Europa League hopefuls with a chance in the cups – in the good years.

That may prove to be their fortune this season, but had Jermain Defoe stretched a little further, a little quicker, at Eastlands in January they might well still be maintaining Tottenham's first serious title challenge in a generation. If Modric has not played quite as well as last season, when most Spurs fans viewed him as of greater significance than the more acclaimed Bale, he has still been highly influential.

But what if Modric, with his eye for a quick pass, his ball-rotation and ability to play across midfield, had gone to Chelsea? It is not too fanciful to envisage him on the left of a diamond midfield, with Ramires on the right, Juan Mata in the hole and Fernando Torres and Daniel Sturridge in attack. That is a mobile, fluid attacking line-up, much more in keeping with Villas-Boas's remit to overhaul and quicken the team. Instead on August deadline day Chelsea signed Raul Meireles, who has many qualities but is no Modric. Villas-Boas then found himself caught between modernising and surviving, trying to phase out Frank Lampard and Didier Drogba, but frequently needing them to rescue results. It was an unhappy paradox which he failed to resolve.

With Chelsea again in flux it is Manchester United who are most likely to test Levy's resolve this summer. At 26 Modric is entering the prime of his career and will want to maximise both his earnings and chances of winning trophies. Much will depend on where Spurs finish, and whether Redknapp stays, but with Modric under contract until 2016 Levy still has the upper hand.