The £12.5m transfer that got away from Tottenham Hotspur - and could now cost Ange Postecoglou

In the summer, Federico Chiesa’s agent was eager to secure a move for him to Tottenham Hotspur. He had held talks with Chelsea and other clubs, but Tottenham was the preferred destination for several reasons—one of them being that, in recent years, several Juventus players have made successful transitions there.

Rodrigo Bentancur, who struggled at Juventus, has found a home in North London, flourishing in his role. Then there’s Dejan Kulusevski, who has been even more impressive, playing in various roles. 3 Added Minutes understands that Chiesa has a good relationship with both players, which made Tottenham his preferred choice.

Tottenham's former director, Fabio Paratici, was also quietly supportive of the move. However, the interest from Tottenham never materialized, and Chiesa eventually joined Liverpool. There have been misconceptions about Chiesa's ability, but he embodies the kind of player Ange Postecoglou would appreciate, given his versatility. Chiesa has the speed and skill to excel and could have been a significant asset in North London.

Tottenham are struggling now, with Richarlison and Son sidelined due to injuries. A player like Chiesa, who knows how to score and create chances, could have been invaluable. The transfer fee, reportedly around £12.5 million, would have been a bargain for a club like Tottenham, giving them a player capable of solving multiple issues.

The injury concerns

Some critics pointed to Chiesa’s injury history as a reason Tottenham did not pursue the move. However, he played 33 league games last season, scoring nine goals, and added four more appearances with a goal in the Italian Cup. In total, he made 37 appearances with 10 goals. The label of being "injury-prone" seems exaggerated, especially considering his recent absence at Liverpool is due to a minor knock rather than a serious injury. Liverpool’s style of play and squad dynamics are different, which may have influenced his current situation.

The lack of depth in Tottenham’s squad has become evident, as there has been little impact from the bench or when key players are sidelined. With Spurs aiming for their first major trophy since 2008, the missed opportunity to sign Chiesa could prove costly as the season progresses.

They have already suffered significant setbacks this season—the draw at Leicester was disappointing, the home defeat to Arsenal was painful, and the loss to Brighton was equally frustrating. As a result, they enter the London derby this weekend needing a positive response, or pressure could mount on the manager. Squad planning and quality depth are crucial for a manager’s success. Ultimately, the decision not to sign the dynamic Italian at such a reasonable price could haunt Tottenham in the long run.