Yahoo Sport 
Daniel Levy facing biggest test of his reign after Manchester City outclass Tottenham in Carabao Cup final
Ryan Mason’s suggestion that Spurs are “four or five years” behind Manchester City after the most one-sided of cup finals will not be the reassurance Harry Kane is looking for when he considers his future in the summer.
At 29, Mason has time on his side as a manager, years ahead for more occasions like yesterday’s, but as a player Kane does not. He will be 28 in July and, in another half-decade, will surely be past the peak of his powers.
There is little chance the England captain would be happy to start another five-year cycle in the summer, just as Spurs did in 2014 with the appointment of Mauricio Pochettino.
Reassuring Kane that Spurs can return to challenging for the biggest trophies in the short-term is just one element of Daniel Levy’s pivotal summer ahead.
Levy’s high-risk gambles have spectacularly backfired in the past 18 months, from sacking Pochettino and replacing him with Jose Mourinho, to involving the club in the doomed European Super League. His popularity dented, perhaps irreversibly, and with the club’s Supporters’ Trust calling for his head, the chairman can scarcely afford to make any further missteps in the summer.
As well as placating Tottenham’s crown jewels, Levy must also rebuild the squad during the harshest financial conditions in decades and, most importantly, appoint a new manager.
Even before the 1-0 defeat to City in the Carabao Cup Final, clinched by Aymeric Laporte’s late goal, it felt like Spurs were at a crossroads.
Mourinho was supposed to take Pochettino’s squad forwards and haul them over the line in finals with his experience and win-at-all-costs mentality.
For all the questions about whether Spurs might have fared better with the Portuguese in the dugout at Wembley, the squad went backwards during Mourinho’s 17-month tenure and Spurs feel further away from winning a trophy now than after their 2019 defeat in the Champions League Final — the natural end of Pochettino’s five-year cycle.
On yesterday’s evidence, Mourinho left Mason with a group of players low on confidence and ill-suited for the attacking principles that a new, modern head coach like Julian Nagelsmann would immediately want to restore.
Mourinho’s failure was another blow to Levy and getting the next appointment right is now one of the biggest calls of his chairmanship.
His previous appointments have been hit and miss and often tended to be a reaction to what has come before, with Spurs veering from Juande Ramos to Harry Redknapp to Andre Villas-Boas to Tim Sherwood.
The decision to replace Pochettino, a progressive coach committed to building for the future, with the game’s foremost pragmatist in Mourinho was the biggest gearshift yet.
With Tottenham’s attempts to earn short-term success under Mourinho having failed, the logical conclusion for Levy is to return to a project coach, who can rebuild while operating under ENIC’s thrifty business model.
And yet, to keep the likes of Kane and Heung-min Son, who is 29 in July and yet to sign a new contact, happy, Levy also has to be able to guarantee a competitive Spurs next season. It is a difficult balancing act. Together with the new manager, Levy also faces the immediate challenge of rebuilding the core of a squad which had gone stale even before Mourinho’s appointment.
Spurs legend Glenn Hoddle has told Standard Sport that the club need a “real revamp in every department of the pitch”. While that is perhaps strong, there is little doubt that Spurs are four or five players away from being competitive at the top end of the Premier League — and that is assuming they can keep their current stars and offload unwanted dead wood.
In the short-term, Mason’s task is to lift his devastated players for the final Premier League push to ensure the club can play European football next season.
For all his potential, Mason’s inexperience showed in front of nearly 8,000 spectators at Wembley, as odd team selection and substitutions contributed to an afternoon of total dominance from the holders.
There are obvious financial reasons for the enormous gulf between the two clubs, which has grown since Spurs beat City in the Champions League quarter-final two years ago, and Mason is one of the last people to blame for yesterday’s mismatch.
Levy now faces one of the most crucial spells of his 20-year chairmanship to ensure Spurs can close the gap and remain competitive in the here and now.
Read More
More cup final heartache means big decision looms for Harry Kane over Tottenham future
Tottenham need ‘rebuild in every department’ - but they won’t spend the money, says Glenn Hoddle
Manchester City vs Tottenham player ratings: Kevin de Bruyne shines as Harry Kane is frustrated
Man City and Tottenham players’ Carabao Cup Final emotions highlight folly of Super League arrogance
