Three big mistakes Tottenham have made in recent transfer windows.
Tottenham Hotspur have come close to achieving some of the incredible success Liverpool have had in recent years. Twice, Spurs fell just short of winning the Premier League title, only to lose out to eventual-champions Leicester City and Chelsea. Just a year ago, Spurs made the Champions League final.
Had things gone slightly differently, under Mauricio Pochettino, Tottenham could sit here today having won both the Premier League and Champions League. Instead, we’re still talking about the team’s search for their first trophy since Juande Ramos was in charge. That alone tells you all you need to know about how long it’s been since Spurs last won a major competition.
Of course, some of that is bad luck. Had Liverpool not been awarded a penalty in the opening minutes of the Champions League final, which looked to be a very harsh decision, maybe the result would’ve been different.
But luck can’t be blamed for everything. Tottenham have cost themselves far too often, letting some great opportunities slip. Just when you think the club will push on, such as after reaching the final of Europe’s biggest competition, they leave us wondering “what if”?
Things could’ve gone a lot differently. Let’s look at three big mistakes Spurs have made 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.
Allowing Christian Eriksen’s deal to run down
Tottenham’s mistake wasn’t selling Christian Eriksen — he’d made his decision to leave. The mistake was allowing his contract to run down as far as it did, giving Spurs no leverage in negotiations and having to accept an offer far lower than Eriksen’s value.
All summer long, the question was whether Eriksen would be sold. But as he only had a year remaining on his contract, Spurs weren’t able to land big money for their star player. Instead, Inter Milan got a bargain by signing Eriksen for less than £17 million in January.
Allowing Eriksen’s deal to almost reach its end was a move we often see from the other North London club, but not Tottenham. A couple of years earlier, Spurs should’ve offered Eriksen a new multi-year deal. If he turned down every offer, that would’ve been the sign to sell him. If Tottenham had made Eriksen available two years earlier, while Spurs were flying high in the Premier League, they may have been able to make £80 million for him.
Selling Eriksen wouldn’t have been a popular decision, but if he had his heart set on a move elsewhere, the opportunity to ask for a big transfer fee was much earlier than Spurs eventually sold him. Instead, Tottenham lost a key player for a bargain price. And that’s bad business.
Missing out on Bruno Fernandes
It’s yet another missed opportunity for Tottenham in the transfer market. Spurs fans know all too well about seeing their club linked to star players only for the deal to fall through. It’s happened so often, from David Villa to Eden Hazard and, as mentioned earlier in the article, Jack Grealish.
Another target was Bruno Fernandes, whose incredible start to his Premier League career helped lift Manchester United back into the Champions League. Fernandes scored eight goals and had seven assists after signing with United in January. That included a penalty against Spurs.
But he could’ve been playing for Tottenham, not against them.
Once again, Levy didn’t match the asking price, a move that could’ve cost Tottenham millions more as Fernandes helped United finish ahead of Spurs and secure Champions League football.
According to the Manchester Evening News, Sporting president Frederico Varandas said that Spurs had made an offer of 45 million euros in the summer with 20 million in add-ons, but those add-ons were “winning the Premier League and the Champions League”.
You can hardly blame Sporting for being unwilling to accept that offer. And just months later, United signed Fernandes for a deal worth up to £67.7 million (80 million euros).
Imagine a Spurs attack featuring Harry Kane, Heung-Min Son, Giovani Lo Celso, Dele Alli, and Bruno Fernandes. Instead, Spurs have to watch Fernandes dominate at a rival Premier League team.