This season is Daniel Levy's last throw of dice at Tottenham Hotspur

Since beginning his tenure as chairman of Tottenham Hotspur in 2001, Daniel Levy has pushed Spurs to be one of the "Big Six" in the Premier League. This has been achieved by promoting youth and making shrewd deals in the transfer market. However, they still don't have any silverware to show for it apart from a League Cup (2008).

The term "Spursy," which is near-synonymous with failure, hurts even the most passionate Spurs fans. Time after time, the club have reached the pinnacle of winning a trophy but have failed at the last hurdle, often displaying shocking performances.

Tottenham under Mauricio Pochettino could have achieved so much more

Tottenham Hotspur v Liverpool - UEFA Champions League Final 2019

There always seems to be a mismatch between football and board decisions at Tottenham Hotspur. Mauricio Pochettino created a young, dynamic team. But during the latter part of his tenure, his requests for fresh investments in the squad fell on deaf years.

Pochettino's requests were rejected by Daniel Levy, citing the costs of building a new stadium. As feared, the squad declined sharply, despite managing to reach the Champions League final in 2019 and losing it. Pochettino was sacked midway through the following season.

A refusal to spend money has been a recurring theme during Levy's stewardship at the club, and was most highlighted during Pochettino's tenure. While it is not expected that they will rival Manchester clubs and Chelsea with their spending power, a net spend lower than the likes of Burnley and West Bromwich Albion between 2014-2019 has been criticized from various levels, including the fans.

Jose Mourinho and Mauricio Pochettino had very different footballing philosophies

Pochettino's sacking midway through the 2019-20 season raised eyebrows, but even more surprising was his replacement, Jose Mourinho - Chelsea's most decorated manager. Daniel Levy thought that Mourinho's winning mentality would earn Spurs some silverware.

Mourinho was everything that Tottenham were not. The Portuguese was a serial winner who demanded instant success and big spending in transfer windows to bring in experienced, older players. Above all, his style of play has often been described as "pragmatic," very different from Pochettino's high pressing and dynamic style of play.

Mourinho, true to his record, took the team to the League Cup final in his first full season. Surprisingly, the former Chelsea and Manchester United manager was sacked days before the final. The club were seventh in the league then, five points off Champions League qualification. Ryan Mason was appointed as interim manager but Tottenham still finished seventh and lost the final.

Daniel Levy got his managerial decisions all wrong since Pochettino

Daniel Levy, known to be a smooth operator off the pitch, came under intense scrutiny and criticism for his decisions following the sacking of Mourinho. Tottenham's managerial search in the summer of 2021 intensified the criticism further as the club ran through a list of candidates for the top job.

Levy hired Fabio Paratici as sporting director from Juventus. The club sounded out multiple managers, including Hansi Flick, Brendan Rodgers, Mauricio Pochettino, Antonio Conte, Paulo Fonseca and Gennaro Gattuso.

In the end, Tottenham hired former Wolves manager Nuno Espirito Santo. Nuno's style of play was far from the "attacking" brand of football Levy promised and four months into his tenure, he was sacked. This led to a barrage of criticism at Levy for hiring him in the first place.

Will hiring Antonio Conte be a repeat of Mourinho?

Paratici and Levy combined to hire Antonio Conte, another former Chelsea manager. Antonio Conte is often termed as the modern day Mourinho. He has short tenures at clubs, wins, and often leaves after a falling out with the board, especially regarding transfers.

Conte's explosive nature was on display after an extraordinary press conference post a 1-0 defeat to Burnley.

Daniel Levy knows he cannot justify Spurs not winning any major trophies any further. They have a state-of-the-art modern stadium, training ground, and some very good players. But as a squad, they are far behind the likes of Manchester City, Liverpool and Chelsea.

To further complicate matters, rival teams are making significant investments. Tottenham cannot lose ground against any of these opponents, and for that they cannot lose one of the best coaches in the world. If Antonio Conte leaves, it will be near impossible to find a manager who can translate the talents of Son Heung-min and Harry Kane into some silverware.

Daniel Levy is finally backing his manager

The winter transfer window last year was a clear example of Daniel Levy finally backing the manager. Deadwood and fringe players were either sent out on loan or sold. Fabio Paratici did his magic and brought in two star players like Rodrigo Bentancur and Dejan Kulusevski. This resulted in Spurs qualifying for the Champions League.

The board and wwners (ENIC group) backed the manager by injecting £150m cash to improve the squad. Paratici has made good use of that money till now, signing Fraser Forster, Richarlison, Ivan Perisic, Yves Bissouma and Clement Lenglet (loan).

Daniel Levy recognizes that now is as good a time as any for this squad to win and he will not find a better manager to do so. A last throw of the dice for him. After all, if anyone can stop Spurs from being "Spursy", it is Antonio Conte.