Former Tottenham manager and club advisor David Pleat says the £100 million signing of Jack Grealish by Manchester City effectively shut the door on a transfer for Harry Kane from Tottenham Hotspur — and that the club’s hierarchy never even made the call.
Speaking on the “No Tippy Tappy” podcast, Pleat recalled the summer of 2021, when Kane was strongly linked with a move to Manchester City. “When City signed Jack Grealish for £100 m, that was the end of Harry Kane going to them,” Pleat said. “According to Daniel [Levy] they never picked up the phone. It was all paper talk, that £150 m…”
He added that, had the deal progressed, he advised Spurs’ chairman to push for more than just cash. “I told Daniel at the time, ‘If you get whatever you think he’s worth or eventually agree, make sure you get two players from Man City’s academy; [Liam] Delap and [Cole] Palmer.’ I did say that.”
At the time, the potential transfer seemed promising: Kane, a proven goalscorer, had made clear his desire to compete at the highest level, and Manchester City were searching for an elite striker to complement their attack. But Pleat believes the Grealish deal gave City their attacking ambition, and removed impetus for them to pursue Kane.
Rather than opening formal negotiations, Pleat suggests planning never advanced beyond media talk and speculation. According to his account, Spurs never validated the interest with a direct approach — a decision which Pleat now regards as a missed opportunity to gain not only cash but also young talent from City’s academy pipeline.
Since then, Kane remained at Tottenham until a move away in 2023, while Grealish has become a key part of Manchester City’s squad following his arrival from Aston Villa. The episode now tells a story of what might have been — a big chance for Tottenham to cash in on their star forward and re-invest, which Pleat believes they failed to pursue aggressively enough.
For Spurs fans and football analysts alike, Pleat’s remarks serve as a fresh insight into one of the most discussed near-moves in recent Premier League history — revealing that sometimes the most significant factor is not simply what happens on the pitch, but the decisions made behind the scenes.
