It has been made clear for all to see that the current Tottenham team is stagnant. Not enough players have been moved on from the Pochettino era and not enough new blood has been brought in to rejuvenate the mentality within the club.

However, I want to take this opportunity to look into the clubs greatest missed opportunities within the transfer market over the last three years.

Paulo Dybala

The Dybala debacle haunted me for weeks on end. One of the most exciting players in Europe looked to be a done deal and would be joining the Lilywhites in the summer of 2019 for a reported fee of €70 million (The Independent).

The deal would ultimately fall through in the final stages after complications with the image rights attached to the player.

It surfaced in multiple Italian media outlets that Dybala’s image rights would cost Tottenham up to an additional €40 million (The Independent) and proved to be the deal-breaker for Levy, seeing him pull out from the deal and let Dybala slip away.

This, however, would only be the start of Tottenham’s shortcomings in the European transfer market.

Jack Grealish

Grealish is the one that personally hurts me the most. Villa were stuck in the Championship and their star player was looking for a way into the Premier League.

This way back would come in the form of Tottenham Hotspur. Spurs came in for the attacking midfielder, having been already had a few bids turned down, including a ludicrous initial bid of £3 million plus Josh Onomah to start negotiations (The Mirror).

It has since come out that Villa would have been happy to let the England international leave for around the £40 million mark (The Telegraph).

Hindsight is a wonderful thing and seeing the heights that Grealish has now reached, £40 million seems like a bargain. Unfortunately, the Tottenham hierarchy did not quite see it this way, never agreeing on a suitable fee that would see Villa part ways with Grealish.

Bruno Fernandes

Fernandes is the main man in a Manchester United team that is currently tabling a very unlikely title charge. The Portuguese midfielder is widely considered one of the best players in the world and has transformed the Manchester club in just over a year.

However, just before this move, it was in fact Tottenham who were front runners to secure the signature of the 26-year-old (Sporting Clube de Portugal).

Levy opted in the end to sanction a deal for Argentine Giovani Lo Celso. As much potential as the Spurs faithful might believe Lo Celso has it is quite clear looking back that the wrong call was made.

Had Spurs met Sporting Lisbon’s valuation of £50 million (Sporting Clube de Portugal), we may have been looking at this season with a much more positive feeling.

Once again, we are looking back on a missed opportunity rather than a wonderful piece of business.

Ruben Dias

We now turn our attention to another Portuguese national currently employed in Manchester. Mourinho quickly identified frailties in the Spurs defence and so attention was turned once again to Liga Nos to solve these glaring issues.

Reports at the time suggested that Tottenham would struggle to prise Dias away from the Portuguese outfit (Football.London’s Rob Guest).

This presumably would be down to the climate in a COVID world where all business whether football or otherwise had taken a hit financially.

We cannot help but again look at the way Dias has adapted to the Premier League and subsequently transformed into a world-class centre back and be somewhat disappointed with another missed opportunity to really improve the squad’s quality.

Milan Škriniar

Finally, we move to the most recent display of transfer market disappointment with the Slovakian international, Milan Škriniar.

Tuttosport stated that Tottenham had serious interest in the defender during the 2020 summer window with talks being held between Inter Milan and Spurs.

However, it ultimately came down to a discrepancy in valuation between the North London club and the Milan based side. An asking price of £50 million was set, however, Spurs deemed a price of £30 million to be more reasonable (Football Insider).

This saga went on for weeks before the window closed, and an agreement was never reached. Unfortunately, this is a case of the same story we have seen multiple times just with a different name.

As we can see it has been a rough few years in the market for Tottenham and fans will be hoping to see considerable improvements in getting big deals wrapped up quicker and smoother in the future.

If this does not change the club always runs the risk of being left behind by other top sides who are more willing to part with funds to secure their place in future title chases.

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