It's fair to say that some Tottenham fans feared a repeat of the Jack Grealish transfer saga when it came to the club's summer move for James Maddison. About to enter the final year of his Leicester City contract and destined to leave the King Power Stadium following their relegation from the Premier League, any low offer from Daniel Levy would have opened up the door for others to come in and potentially see Tottenham lose out on a priority target.
That was not the case, however, as Spurs saw their £40million offer accepted and the England international went on to pen a long-term deal at Tottenham Hotspur Stadium in the process. Five years earlier, Spurs had their eye on another Championship ace but a deal for Grealish never came to fruition.
Viewed as a player that Mauricio Pochettino could take to the next level as he plotted Tottenham's bright future, Grealish himself was certain that he would become a Tottenham player and a £25million transfer appeared to be set in stone. A move never materialised, though, and it proved to be a golden opportunity wasted for Levy and Spurs, especially with the attacker going on to new heights before joining Man City for an eye-watering £100m fee three years later.
While Pochettino and the club's fans were left to rue Tottenham's failure to sign Grealish, thankfully the same didn't happen with Maddison five years on. The 26-year-old has made an immediate impression during his first month with the Lilywhites, including in Wednesday's 5-1 pre-season win over Lion City Sailors in the final friendly of their Asia-Pacific pre-season tour.
Showing some good touches and glimpses of his quality against West Ham, this time he had a greater influence on proceedings and on another day would have
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