The prospect of Harry Kane making a sensational return to Tottenham has stirred excitement among fans. Still, doubts persist as Daniel Levy's tenure casts a shadow over any potential reunion. While the Tottenham chairman confirmed the existence of a buy-back clause in Kane's deal following his move to Bayern Munich, the intricacies of this clause remain uncertain.

According to the reports from Fabrizio Romano, the clause doesn't simply constitute a straightforward buy-back option for Spurs. Instead, it gives Tottenham the first opportunity to re-sign Kane if he returns to the Premier League. Moreover, no fixed price leaves room for negotiations with Bayern Munich. Official details of the clause are yet to be confirmed by either Tottenham or Kane's representatives.

Crucially, doubts linger about whether Kane would entertain returning to north London while Levy remains at the helm. Despite heading into the summer transfer window with Kane's future hanging in the balance due to his expiring contract, the striker showed no inclination to extend his stay.

Levy, keen to avoid losing Kane for free in 2024, faced a dilemma, leading to a tense negotiation process before sanctioning Kane's move to Bayern. This strained relationship culminated in delays and complications in the deal. As Kane embarks on his new journey with Bayern, the frosty relations between him and Levy pose a significant hurdle to any potential return to Spurs, despite the striker's aspirations to break Premier League records and win titles in England's top flight.

Meanwhile, Levy has openly admitted that the appointments of “trophy managers” like Jose Mourinho and Antonio Conte were perhaps a mistake. The chairman wanted to win but acknowledged that the pressure for instant success led to misguided managerial choices, ultimately shaping the club's current direction under Ange Postecoglou. As Tottenham navigates its path forward, the possibility of a Kane return remains enigmatic, with Levy's presence casting a long shadow over the striker's future in north London.