Why are Tottenham whiffing on so many potential transfers?

With the summer transfer deadline just two days away, Tottenham still have work to do. Just what is keeping them from sealing any deals?

Tuesday brought news that once-upon-a-time Tottenham target Pape Cheikh Diop has signed with Ligue 1 side Lyon, while Lazio’s Keita Balde made the move to Monaco. These are just the latest Spurs transfer rumors to be quashed in a summer of deflated expectations.

Before Diop and Keita there was Borussia Dortmund centre-back Matthias Ginter, Genoa’s Giovani Simeone and Porto’s Ricardo Pereira — plus plenty more links with players that either moved to other clubs or show no signs of budging.

In fairness to Tottenham, there have been some successes. The club moved quickly to land record signing Davinson Sánchez from Ajax, and a rumored third choice goalkeeper soon followed in the form of Paulo Gazzaniga. While those players are exciting in their own way, they don’t represent the full extent of the business required before the transfer window closed on Thursday.

Spurs really do need players like Diop — a young central midfielder with oodles of potential — and Keita — an experienced winger that would add a sharp point to Spurs’ attack. They also need a right-back after Kyle Walker’s departure and another option at striker, especially if Vincent Janssen either earns a last minute move or proves to be dud for a second season running.

All of these needs are plain to see, and have been for most of the summer. So why haven’t Tottenham acted with anything approaching haste?

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In all likelihood, club chairman Daniel Levy has acted — just not to the liking of the potential selling clubs or the prospective players themselves.

The thriftiness enforced by the construction of a new stadium means Levy is likely even more prone to low-balling both transfer bids and player salaries than he was before. That is what the club needs to do to remain solvent, so it’s hard to fault Levy on that point. This summer’s transfer window was always going to be a slog in that sense.

So then why haven’t the club acted sooner? Tottenham’s financial situation and its affect on its bargaining power were well established years ago. Why wasn’t there a concrete plan in place to get what needed to be done early, or at the very least get the wheels turning? Why do they have so little to show with only 48 hours left in the transfer window?

It’s not like the club were prohibited from getting a headstart. Look at Monaco. The Ligue 1 side were under no illusion what their future would hold. They were going to lose a sizable chunk of a thoroughly impressive team this summer whether they liked it or not.

Far from resigning themselves to that fate though, they proactively went about finding replacements for the likes of Bernardo Silva, Benjamin Mendy, Tiémoué Bakayoko and others.

The club’s first business actually happened in the spring, well before the transfer window opened, when they agreed a deal to sign Anderlecht youngster Youri Tielemans.

The 20-year-old Belgian prodigy had been a staple of Tottenham rumors for years. Spurs could have recruited him. He would have come cheap — Monaco paid just north of £20 million for the playmaker. Yet Spurs stood idly by while another team acquired yet another missing piece of the puzzle.

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In hindsight, that transfer presaged a whole summer’s worth of missed opportunities. Fans and many pundits resisted the urge to call out Spurs’ lack of activity while their rivals splurged. They were biding their time, waiting for the market to settle, or just content with what they had.

Now, after another slow start to a campaign, Spurs join the rush to make important decisions much too quickly, while likely spending — and risking — more than they ever intended.