One of the (many) major criticisms of Tottenham Hotspur over this season’s under-performance is the executive structure — how it’s structured, who reports to who, and their effectiveness in the job. Yes, this is another backhanded criticism of Johan Lange, but there’s new reporting from our good friend Matt Law in the Telegraph that says Spurs might — just might — be doing something smart.
According to Law, Spurs are actively in the process of searching for a new Sporting Director to replace the outgoing
Fabio Paratici, and have made inquiries about Chelsea’s Paul Winstanley and former Palace director Dougie Freedman.
Winstanley has been one of the people responsible for implementing Chelsea’s wacko transfer churn methodology since the new ownership took over a number of years back. Say what you want about Chelsea’s transfer blitz — it’s kind of worked out for them! It’s not clear whether Winstanley was in charge of that operation or just worked to implement it, but it’s rather impressive regardless. Law says that he was recently given a contract extension at Chelsea until 2031 which makes him perhaps unlikely to make the switch, though I’ll point out that contractual obligations can easily be fixed by offering lots of money.
Dougie Freedman, meanwhile, was Sporting Director at Palace from 2017 until this year, when he left to take up a similar position in Saudi Arabia with second division club Al-Diriyah. The answer to why he’d leave a good job at Palace for a second division club in the Kingdom can probably be answered by a Brinks truck filled with money, but it should also be noted that players, managers, and executives in KSA tend not to stay long after they’ve earned a couple years of bank. Law doesn’t think Freedman would necessarily want to leave so soon after joining Al-Diriyah, but who knows. Freedman has also been a Premier League manager, in charge of Crystal Palace, Bolton Wanderers, and Nottingham Forest, before rejoining Palace as Sporting Director.
The Telegraph also notes that Spurs are looking at other, unnamed candidates. It is expected that whoever takes the position would have a great amount of input as to who would be offered the permanent head coaching position when the 2026-27 season starts.
I would say this — whether or not Winstanley or Freedman are convinced to take the job is almost immaterial at this point. It does, however, provide some evidence that Spurs are actively making smart decisions and looking at smart people to fill Paratici’s vacant position. It’s also not known what this means for Lange — he’s come under a lot of criticism, and not just from me, for how he’s built the playing squad over the past number of years, so it’s unclear whether the new Sporting Director would be a co-SD model like Lange and Paratici had earlier this year, ahead of Lange, or even replacing him entirely. I know which one I’d favor, but we don’t actually know.
This is actually encouraging. Regardless of what happens with relegation, it would be catastrophic for Spurs to not have their executive and recruitment structure in place when the summer transfer window opens, especially when the club needs a permanent manager as well. Whoever takes the job will have a HUGE task list, not only helping to appoint a manager, but also potentially doing a major squad refresh. Hopefully it’s someone good, but this report at least points to a good process. I’ll take it, for now.
