Daniel Levy must regret selling ‘brilliant’ Tottenham defender in 2021 who’d thrive under Ange Postecoglou

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Tottenham Hotspur have just under two weeks to complete any final pieces of transfer business before the window shuts.

Ange Postecoglou has been handed his latest recruit on Friday with the signing of Wilson Odobert from Burnley.

This now means Tottenham have brought five players into the club this summer, albeit with Timo Werner returning on loan and Yang Min-hyeok arriving in January.

But there is certainly still room for improvement with some key positions still potentially needing to be added to before the end of the month.

There have been questions surrounding the backup positions at full-back this summer with Tottenham reportedly preparing a £27m bid for right-back Vanderson.

However, an alternative for Destiny Udogie on the other side of the pitch is also a position which Tottenham could really do with strengthening.

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Ben Davies cannot replicate Destiny Udogie’s attacking threat

In Udogie, Spurs have a seriously impressive attack-minded left-back who showed in his debut season just what he is capable of.

With Pedro Porro on the other side of the pitch, Postecoglou has two seriously dynamic full-backs.

However, Spurs saw last season how the production dropped when Porro and Udogie were sidelined through injury.

Ben Davies has proven himself to be a superb servant for Tottenham having now been at the club for 10 years.

However, he does not offer the same level of attacking prowess that the Italian defender does when he’s available.

Tottenham made big mistake in selling Dennis Cirkin

Going into the 2024/25 campaign, Spurs are going to need a squad filled with quality so Postecoglou can rotate freely across the numerous competitions.

And Sunderland’s Dennis Cirkin is proving himself to be just the left-back Tottenham could do with to provide backup to Udogie.

The irony is Tottenham sold him to the Black Cats back in 2021 after coming through the ranks in north London.

Since leaving, Cirkin has established himself in the Championship with Sunderland and has gotten off to a stunning start this season.

After providing an assist in their season opener last weekend, Cirkin scored the opener on Sunday for Sunderland against Sheffield Wednesday.

His goal was hailed as ‘brilliant’ by the Sky Sports commentator as he landed his sixth goal since signing for the Wearside club.

Tottenham have missed out on their buy-back clause for Dennis Cirkin

After selling Cirkin to Sunderland back in 2021, Spurs included a buy-back clause in his contract which could have seen them bring the defender back for a fee of £6m.

That clause has now expired with June 2024 marking the end of Tottenham’s opportunity to provide Cirkin with a return.

Of course, the left-back would not be guaranteed the game time which he gets at the Stadium of Light, but he could have thrived under Postecoglou.

Cirkin’s 2023/24 season was curtailed through injury but the signs were promising with the Sunderland defender providing 1.96 shot-creating actions compared to Udogie’s 2.15, per 90 minutes, according to FBRef.

Spurs need an attacking left-back as backup to Udogie and Daniel Levy may now be regretting the decision not to keep Cirkin around back in 2021.