While Tottenham Hotspur have certainly improved, they may be walking the rocky road to a trophy-less nowhere.
There’s something of a conundrum occurring at Tottenham this season. The North London club has reached a cross-roads of identity, a point where they must decide in which direction they’ll go over the next few seasons. All the work put in to build Spurs into a top-calibre side could be for nothing, should they fail to win a trophy this season. It doesn’t take that long a look at the current state of Spurs to realise how crucial silverware is to their short-term future. This is a side that’s never far from conversation of the potential winners of the Premier League in the last couple of years, yet they haven’t won any trophies since their League Cup triumph in 2008. 
 
Spurs are currently building a new, state-of-the-art stadium, a sign of their intent to be a major player in English and European honours. They have a talented young core of players that have come through the system, or been shrewdly brought in by a combination of great scouting and Daniel Levy’s expertise in the transfer market. The squad is led by one of the best young managers in the world in Mauricio Pochettino, however it seems Spurs are seemingly re-entering a cycle they have struggled to escape from in the last few decades. The cycle goes as follows: Have average squad, bring in new manager, buy and build up talented players, win nothing, sell great players at massive profit (mostly to Real Madrid), fire manager, have average squad, bring in new manager…and the cycle continues. 
 
Right now, Spurs are between the stages of building valuable players, particularly in Harry Kane, Dele Alli, and Christian Eriksen, and winning no trophies. Some Spurs fans, while delighted with the progress made under Pochettino, are looking at Manchester United, Manchester City, Chelsea, and arch rivals Arsenal win while they watch. Real Madrid have peaked their head in the direction of White Hart Lane once again, with rumoured interest in Harry Kane and Dele Alli the topic of conversation. It has flashbacks of the 2011 season, when Chelsea’s Champions League win knocked them out of the following season’s competition. Just over a year later, two of the finest players in the world, Gareth Bale and Luka Modric, had left for the pastures of the Bernabeu. 
 
The sharks are circling to pick off Spurs’ players once again. Manchester United are planning a raid of Danny Rose and Eric Dier. Barcelona see Eriksen as the replacement for Iniesta, and Real Madrid are looking to add a couple more Galacticos to they’re already stuffed ranks. Pochettino won’t be Spurs manager forever, especially given the reputation and admiration he has earned, and the volatile ‘win now’ managerial landscape. The club has a strict wage structure, so they can’t match the amounts opposition teams offer in wages. There are only two ways to convince the players to stick around: Remind them how much they love Spurs, or win trophies. The way club football has gone now, the former is nothing close to a dependable option, so only one remains; Spurs must win now.