Notably, was he right to make public a dressing room dressing down for his players? Will he lose their respect or sharpen their focus ahead of a fortnight that could have a huge impact on his and the club’s future? Was it a refreshing blast of honesty from a man new to management and unafraid to speak his mind, or the rash ramblings of a naïve newbie, who may live to regret his words?
And there is a wider question that Sherwood addressed, in his follow-up interview a few days later, when he said: “They are men, and I’m a manager not a babysitter.”
Are today’s highly-paid professional footballers just a little detached from the real world, too cocooned in their own image rights and the trappings of wealth, to be able to deal with adversity and criticism.
Sherwood’s words certainly resonated with a lot of the fans who buy the tickets and TV subscriptions that ultimately pay those players the sort of salaries that make City bankers look like charity workers by comparison.
While former professionals were lining up to warn Sherwood that public criticism can lose the dressing room, others, including fans of all hues, were pleased to hear Sherwood shooting from the lip.
There were echoes of Bill Nicholson, the greatest Spurs manager of all, when Sherwood said: “At no football club should you have players who think they are doing you a favour by playing for you. People pay a lot of money to support their club, and the players owe it to them to perform and give 100% for the shirt.”
It is no surprise. Sherwood has long been a forthright character, unafraid of upsetting people around him and confident of his own abilities.
This, after all, is a man who turned down the chance to manage Blackburn Rovers, whom he had captained to the Premier League title, because he fancied his chances of landing the Spurs job long before Andre Villas-Boas was sent packing.
During his playing days he was as combative off the pitch as on it, with little time for the media or hangers-on, not unlike Roy Keane, though without the Corkman’s world-class talent. Like Keane, Sherwood has always had strong opinions of his own and little time for those of others.
The beginning of the end for Glenn Hoddle as Tottenham manager came in that infamous 5-3 defeat by Manchester United, when Spurs had been leading 3-0. Sherwood was one of the senior professionals who spotted Alex Ferguson’s pivotal tactical change before half-time and implored Hoddle to switch tactics in response. Hoddle won the argument but lost the game and the respect of his players, and fell out completely with Sherwood, before selling him to Portsmouth.
Maybe that was the spur for Sherwood to become Tottenham manager. Certainly it seemed an unlikely outcome for a lad growing up in leafy Hertfordshre as an Arsenal supporter, although Harry Redknapp, who would watch the Gunners from the North Bank as a boy, also went on to become the club’s most successful manager in the Premier League era.
Sherwood, who is very close to Jamie Redknapp, has clearly taken on board Redknapp senior’s style in terms of playing and man-management. After taking over from Villas-Boas in December, he immediately ditched the defensive 4-2-3-1 formation and reverted to 4-4-2, although he has tinkered and changed since then.
He brought Emmanuel Adebayor in from the cold to great effect, and has shown faith in young home-grown players such as Nabil Bentaleb and Harry Kane.
His first 10 league games brought seven victories and shot Tottenham into the top four, though recent defeats at Norwich and Chelsea have left Sherwood admitting the prospect of emulating Redknapp by reaching the Champions League is now ‘unrealistic’.
Before Spurs were beaten 3-1 by Benfica at home on Thursday in the Europa League, Sherwood was asked if his public outcry might galvanise the players for this make-or-break period.
“I hope so,” he replied. “They are playing for their futures.”
They are also playing for their manager’s future, which now depends on the unlikely achievement of a top-four finish, or whether Louis Van Gaal decides taking over at Tottenham in the summer is a better option than waiting to see how much patience the Manchester United board have with David Moyes.
The Dutchman was Levy’s first-choice to succeed Villas-Boas and had talks in London, but when he told the Spurs chairman he would do nothing until he had completed his duties with the Netherlands at this summer’s World Cup. Hence Sherwood was appointed on a short, 18-month contract, which hardly sent out a message that Levy had long-term plans or confidence in his new manager.
Yet the pair have had a good relationship for some time, with Sherwood keen on the role of sporting director before Franco Baldini was appointed last summer. Sherwood was also being discussed as a possible manager more than a year before he took over, in the early months of Villas-Boas’ reign when it first became apparent the Portuguese was making the same mistakes he had made at Chelsea, and an equally early exit was a possibility.
When Villas-Boas was granted a stay of execution after a run of good results at the tail end of 2012, he made sure Sherwood was kept at a distance, working only with youth players rather than the first team.
Now Sherwood is the one looking over his shoulder, while the talk around him is about who will be his successor — and how soon.
But remember how Jose Mourinho said he would have substituted all 11 players when Chelsea lost to Newcastle before Christmas? It has not done the Blues too much harm.
Perhaps Levy should consider the riskier business of failing to show confidence in his manager and allowing the rumours of ‘who is next’ to destabilise Tottenham’s season, as they sit fifth in the table with games against Arsenal and Liverpool to come.
But then when was the last time a chairman decided he was to blame for a team’s failings and needed replacing?