Tottenham’s Biggest Transfer Blunder From Each Of The Last 6 Windows [opinion]

Lockdown gives you a lot of thinking time.

When it comes to Tottenham, I’ve mostly been thinking about the usual stuff – failed transfer activity and what could have been, etc.

And I don’t mean if we’d have spent hundreds of millions of pounds more, just if we hadn’t made fundamental mistakes in the market that has left us needing a major squad rebuild once again this summer.

It started going wrong in about 2017. So this article will recap the biggest missed opportunity from each of the past six transfer windows…

MORE: The Bookies’ 5 Most Likely Spurs Summer Signings

January 2020 – Odion Ighalo

It was unforgivable not to sign a striker to cover for Harry Kane, even though there weren’t loads of attractive options. I’m not saying I was disappointed to miss out on Ighalo by any stretch, but he was proving to be a good short-term solution for Manchester United with four goals in three starts and could have been ours had we moved before deadline day.

This is a weak start but trust me it gets much uglier.

Summer 2019 – Bruno Fernandes

Some Spurs fans may view Paulo Dybala as the one that got away from last summer, but that deal for the Juventus star did appear to be a complicated one to get done and thus I don’t think it can be classed as a mistake.

There is no such excuse for not getting Fernandes who was available from Sporting Lisbon and ended up at United six months later for £47m, fee according to BBC Sport. Like Ighalo, he has made an immediate impact at Old Trafford. He’s a goalscorer, creator, a top-class operator, and would have helped fill the void to be left by Christian Eriksen dropping anchor. Had we sold the Dane in the same window we may have been able to afford Fernandes, so perhaps that was the true mistake from this period.

January 2019 – Denis Zakaria /Youri Tielemans

I’ll let ex-Spurs midfielder Jamie Redknapp do the talking on this one…

Sky Sports reported in January 2019 that Mauricio Pochettino had been having Zakaria scouted for years to be prepared for Dembele’s departure. If the Swiss wasn’t available, Youri Tielemans was on loan and would have spared us the dreaded Moussa Sissoko-Harry Winks double pivot.

Summer 2018 – Jack Grealish

As The Sun details, we could have signed one of the Premier League’s best midfielders this season for £6m in 2018. Grealish had said his goodbyes but Daniel Levy wanted to shave a pound or two off the price and ballsed it up.

January 2018 – Janssen and Nkoudou

At the time, missing out on Ross Barkley to Chelsea looked bad business but that now looks like a lucky escape. In truth, the squad didn’t look in bad shape at this point and Lucas Moura has proved to be a decent addition, better than Malcom whose career has plummeted since his links to Spurs.

The mistake, if any during this window, was not being able to recoup any money for the likes of Vincent Janssen and Georges-Kevin Nkoudou who had been written off 18 months into their time at the club and yet were not sold until a year and a half later. Had Levy cut his losses on these two a bit earlier we may have had more money to spend the following summer.

Summer 2017 – Ricardo Pereira

We scouted Pereira as a potential replacement for Kyle Walker in 2017, but his undaunting release clause of €25m was a stumbling block, according to The Independent. He’s made that price look like loose change at Leicester, establishing himself as one of the best full-backs in the Premier League.

Serge Aurier ended up coming in at a very similar cost and has been one of the worst over the same period – another big error of judgment from Levy.

This is how Jose Mourinho’s team could have looked with these players…

Subs: Gazzaniga, Vertonghen, Tanganga, Ndombele, Grealish, Lucas, Ighalo

(Or something similar. Please don’t swear death upon me in the comments).

That looks a hell of a lot better than where we are now. It’s not perfect, but there are only one or two positions of concern compared to five or six now.

And I don’t think I’ve been unrealistic. Pereira would have cost no more than Aurier, and Fernandes, Zakaria and Grealish a similar amount to what we might end up spending on Steven Bergwijn and Gedson Fernandes.

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