In the summer of 2011, when Liverpool were on the lookout for a backup keeper for Pepe Reina and identified Brad Friedel as the target, the American was persuaded to join the Spurs ranks by then manager Harry Redknapp with a promise of more first team games.
Exactly a year later, after an entire summer spent chasing his signature Clint Dempsey, he finally left Fulham, but not for the red of Anfield but for the white of Tottenham.
A few weeks earlier, Gylfi Sigurdsson, a player whom Brendan Rodgers managed at Swansea, snubbed Liverpool in favour of a move Spurs.
This summer too, the same thing seems to be happening. After Liverpool lost their main target Henrikh Mkhitaryan to Borussia Dortmund, they were looking at Willian from Anzhi to fill the void, but again they look set to be beaten to it by Spurs.
There is a trend that seems to be emerging nowadays. Anytime Liverpool look at a particular player and do everything they can to sign him, just at the last minute, they are pipped to the post by some other team.
So what is happening to the once mighty Liverpool? Why is it that every time they look at a player, everything goes according to plan until the last minute when the player does a U-turn and heads off somewhere else?
Whilst the Spurs connection isn’t really a result of spying on Brendan Rodgers as some tabloids will have you believe, it hints at an even bigger problem.
It shows that both the clubs are operating in the same market, for similar calibre stars, whilst also harbouring the same ambitions, that of breaking into the Champions League.
It is one thing for Liverpool to be overlooked in favour of the top four, but it is quite something else if Spurs are now perceived as a more likely Champions League candidate than the Reds.
Liverpool are finally getting to grips with the bitter truth. It is the fact that Liverpool are not who they once where and Anfield is not the pinnacle that every footballer dreams of these days.
It is something their owner John W. Henry recently acknowledged – reputation alone is not enough and that Liverpool must get back into Europe to win the off-field as much as on-field scraps.
In all these failed deals, Liverpool are not just paying the price for finishing no higher than sixth in the previous four seasons, but also for all those high-profile transfer failures, which Henry formed a large part of his early tenure.
In both the Willian and Mkhitaryan cases, Liverpool thought that a deal was in place right until the moment when another bid came in and the whole deal collapsed on its head.
Now, Liverpool have resorted to claiming that Willian was not someone they were looking for.
But just like last year, when they brought in Philippe Coutinho and Daniel Sturridge instead of Dempsey and Sigurdsson, if they can bring in similarly sound alternatives the blow of losing another target to Tottenham will be softened and all will be forgotten again.
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