Speaking on Sky Sports, the former Tottenham and Aston Villa gaffer hasn’t pulled any punches when speaking about the transfer strategy at Tottenham.
Perhaps Tim is broadly echoing fan sentiment?
Tim has repeatedly highlighted what he sees as a pattern of wasteful spending on “average” players, missed opportunities on high-impact talents, and underutilization of academy prospects. His comments come amid Tottenham’s mixed form under head coach Thomas Frank in the 2025/26 Premier League season, where the Spurs sit mid-table despite significant summer investments.
Sherwood effectively accused Tottenham of self-sabotage by dragging their feet in negotiations, allowing rivals Arsenal to “hijack” the £65m deal for Eze. He called it a recurring issue:
“It happens time and time again!”
He argued that Spurs’ hesitation stems from indecisive scouting under technical director Johan Lange and advisor Fabio Paratici, leading to lost targets.
Echoes of the Daniel Levy era, having not quite vanished, after all, perhaps.
Tim blasted the summer 2025 window’s seven major signings (totalling over £250m), claiming most are “bang average” and failing to gel under Frank.
Time Sherwood is far from happy with Tottenham
Xavi Simons (£60m from PSG): Sherwood says the Dutch midfielder has been “starved of creativity” due to poor team balance but could become a “hero” if deployed centrally against Arsenal. However, he questioned the wisdom of the signing given Simons’ adaptation struggles.
Mohammed Kudus (£55m from West Ham): While praising Kudus as “refreshing” and Tottenham’s standout (6 goal contributions in 10 games), Sherwood warned he’s inconsistent and the team is overly reliant on him.
Sherwood’s barbs aren’t new; the very well-spoken pundit has critiqued Spurs’ dealings since his playing days (e.g., his 2003 fallout with Glenn Hoddle), but they’ve intensified this month amid Tottenham’s home form slump under Frank. Spurs spend plenty, but on mediocre players, gaining traction. If Tottenham missed out on another target like Semenyo, expect more fireworks from the ex-Spurs man.