As we do every offseason, Cartilage Free Captain is reviewing the first team players at Tottenham Hotspur, looking back at their performances the past season. Up first: the boss man himself, manager Mauricio Pochettino.

Mauricio Pochettino

Record: 23-8-7
Trophies Won: 0
Record against the top six: 4-1-5
PL Manager of the Month Awards: 0

What went right?

There are two contexts in which Mauricio Pochettino can be judged. The first is as Josh Hill, a contestant on Wednesday night’s episode of Jeopardy, told host Alex Trebek: “He has really turned the team around. We went from being mid-table, Europa League. We’ve been Champions League two years in a row, we’re going to the knockout stage, and we’re just moving forward.” The second, which I will attempt to summarize quickly, is that Tottenham Hotspur, now four years into the Pochettino era, has properly become one of England’s top clubs and should act accordingly. In both regards, he has passed many of the tests.

Pochettino’s Spurs continue their habit of winning in style, and have picked up a habit of qualifying for the Champions League, an accomplishment that has become less of a dream and more of an expectation. The third place finish in the Premier League will be something that satisfies the first context, and in many ways the second, as it required impressive victories over Liverpool, Manchester United, Arsenal, and Chelsea.

The biggest achievement of the 2017-18 season, though, satisfies both the first and second prompts. Topping a group that included Borussia Dortmund reigning champions Real Madrid was a daunting task, but one in which the Argentine got a majority of his decisions right. A moderate switch in style to play more of a counter-attacking game in the opening match of the group against Dortmund at home saw his side come out 3-1 winners in an almost perfect start. The two matches against Real Madrid in particular allowed Pochettino to show that he could not just compete against the world’s most respected coaches, but out-coach them. He did so in the draw at the Santiago Bernabeu, starting a mostly useless Fernando Llorente in a role that suited him and the match. He less shockingly achieved better at Wembley as Dele Alli shone in a 3-1 victory that also saw Kieran Trippier outdo Marcelo in one of the greatest matches of his career.

His management of specific players was also impressive over the course of the season, as he continued to find the balance between letting his players and his system shine. Pochettino worked around Trippier’s strengths and weaknesses to maximize his value to the team, and tinkered with the roles of his attacking quartet of Alli, Christian Eriksen, Son Heung-Min, and Harry Kane to make them even more threatening.

Pochettino is clearly beginning to master, if he has not already mastered, working with pieces that do not always fit to achieve success. That can only be a positive for an incredibly ambitious manager — and club.

What went wrong?

Perhaps the biggest stain this season will be that Pochettino has not won any trophies, and that he belittled the FA Cup along the way. How big a stain and the impact of the belittling are both debatable, However, for the most part, Tottenham are not trophy-less for a lack of trying, particularly outside of Premier League play. There is little indication that they cannot do it in the future, but, of course, they must be wary that they are currently living with the potential of being one of the best sides in England to have not won anything.

Pochettino’s biggest shortcoming, though, is in regards to squad building. He is significantly involved in transfers, and though he is working with a smaller budget than many around him, there is some room for improvement. Bringing in Davinson Sanchez has proved to be a smart move, and the addition of Lucas Moura may also pay off, while Serge Aurier, meanwhile, improved over the course of the season. However, the addition of Llorente was a bigger miss than hit, despite any small contributions. The squad Pochettino has assembled, for large parts of the season, made it difficult for him to improve his side’s chances of a desired result during matches with the addition of substitutes, which has been a problem for him for a few years now.

Additionally, while picking up a backup for Kane might be difficult, arranging his team in the striker’s absence has been incredibly challenging for Pochettino. Some of this may come down to stubbornness; his refusal to try Son at the front was difficult to comprehend in the late stages of the season, but was possibly explained by an ankle injury that he played through.

What’s next?

By the time late April rolled around, it was clear that Pochettino was aware of his and his club’s areas of improvement. He admitted after the FA Cup semifinal defeat to Manchester United that his team needed more time to achieve such things, and following the season finale against Leicester, said he wanted the club to take more risks.

Reports have surfaced that he wants £150 million to spend to fix some of those squad issues, something that ties into his desire to be more risky. Ultimately, it is a desire to achieve greatness, be it in the form of trophies or a remarkably deep Champions League run. All of the other pieces of the puzzle, namely talented players and a smart coach, are already there.

The biggest question surrounding Tottenham next season is whether or not they can achieve that. A significant step forward clearly is something Pochettino expects of himself and his side; he is judging himself in that second context, thinking about Tottenham’s current status in England and in Europe. That means that he has to get the transfers right this summer, and all of the decisions afterward. It is not an impossible task, and the potential is there. However it shakes out, Pochettino has a very important year ahead of him.