Tottenham reportedly once again failed in an attempt to capture Leandro Damiao this past January, with Internacional rejecting the offer which fell well short of their valuation. This one may rumble on, but with each missed opportunity, Damiao may become yet another name who slips through the net.

And you can understand the frustration: Tottenham may be light just a player of Damiao’s calibre to push them over the line for Champions League football next season and keep them there for the next few years. With the windfall of Champions League revenue that would come into White Hart Lane, Damiao should always have been seen as a necessary investment.

Spurs are by no means a small club, and their ambition to establish themselves as a top European side that consistently compete in UEFA’s elite competition should be attractive to most. But it’s not always enough. Tottenham do not have the means to compete with clubs like Manchester City or PSG when big names become available and even losing out to Juventus on Fernando Llorente is not a total surprise.

So you have to ask: should Daniel Levy be brave and roll the dice when players like Damiao express a desire to come to Europe?

On one hand, you can understand Levy’s thinking behind this particular deal. As we’ve seen in the past, there are always a number of parties who have a hand in the rights of players from South America. How far beyond Damiao’s actual worth would Tottenham have to pay? Forget that he’s incredibly talented and showcased his qualities at last summer’s Olympics, but he is lacking in any experience in Europe. Furthermore, would paying for him in, say, January be the last Tottenham hear from ‘third parties’ in Brazil? Damiao will be an important player for Brazil in the coming years, but it is worth it for Spurs?

The thing is it’s not just Damiao that this applies to; Tottenham have missed the boat on many transfer targets because of Levy’s decision to either play the transfer game at the eleventh hour or to try and negotiate the prices down.

It became quite clear that Andre Villas-Boas positioned Tottenham very well in the Premier League ahead of the opening of the January window, and all that was needed was a little investment. Yes Lewis Holtby came in, but the need was for a striker who was of better quality than the options currently available.

It could be the case the Levy is holding out for the summer where prime targets can be acquired, but the latest revelations that Damiao would prefer a move to Italy doesn’t sit well for the Spurs chairman. The Brazil forward is said to be interested in a move to Napoli, with the Naples side likely to be after a replacement for Edinson Cavani. You look to Serie A now and you can understand Damiao’s thinking, with Napoli very much in the title race and equipped with a manager and star names to mount serious challenges.

When it comes to targets such as Damiao and the obvious draw of his name and status in the national team, it has to be asked whether there are other options available that would be seen as safer but equally effective alternatives.

As mentioned, Tottenham shouldn’t have a tough time attracting top names from the continent, and they are more than capable of taking advantage of the financial state of some of the European leagues.

Damiao may be slipping through the net, but it really won’t be much of a shame. A gamble, yes, but not really one Tottenham can afford to make.

The disappointment is that Spurs didn’t strengthen in January, but that is a slightly different topic than them missing out on Damiao altogether.

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