Tottenham: 3 biggest mistakes by Spurs in recent transfer windows

Not signing Jack Grealish

Jack Grealish had a great debut season in the Premier League. Whether he stays at Aston Villa this summer remains to be seen, but at some point down the line, he’s likely to make a move to a big club in the Premier League. Had things panned out differently, he could already be playing at Spurs.

Two years ago, while Villa were still a Championship side, Spurs made a £25 million bid for Grealish. It sure seemed like the deal would be completed, but eventually, Villa turned down the offer. Had Daniel Levy and Tottenham upped the price, it’s possible they could’ve got their target.

Instead, it’s another “what if” moment for Spurs fans. Villa would secure promotion to the top flight the following year, and this past season, Grealish scored nine goals and made seven assists, playing a crucial part in Villa surviving relegation.

Had Spurs got the deal done two years ago, Grealish could’ve been a key starter in Pochettino’s team, and more recently helped the club under Jose Mourinho, had history gone the same way and Spurs made the managerial change.

For a team that too often struggled to get out of first gear and create clear-cut chances in front of goal, having Grealish in the starting lineup might’ve made all the difference.