Harry Kane will not be prepared to become a “nearly man” at Tottenham, says Teddy Sheringham, with the prolific striker likely to seek a move unless Spurs can deliver a major trophy.
Positive progress has been made in north London under the guidance of Mauricio Pochettino, but silverware remains elusive.
Questions are being asked of those on and off the field as a result.
Pochettino was heavily linked with the Manchester United job before Ole Gunnar Solskjaer put himself in pole position, while talk of a switch to Real Madrid refuses to go away.
Kane has also been linked with the Liga giants on a regular basis and his ambition is expected to lead him elsewhere unless a reason to stay put can be offered.
Former Spurs frontman Sheringham told Radio 5 Live: “Harry will want to win stuff. He will be wanting to play at the very top.
“It's going to be a big factor with Harry that Tottenham are moving into a new stadium - but they have to win something.
“At the moment, they are nearly at the top. For me, that's not good enough for Harry Kane because he is tops.”
Kane recorded his 200th career goal for club and country during a 2-1 defeat to Southampton on Saturday.
While he had cause for celebration, another setback has left Tottenham sweating on a top-four finish.
That is considered to be the minimum requirement for a club that has reached the quarter-finals of the Champions League, with more needed to be done if Kane and Co are to remain loyal.
Sheringham added: “There is going to come a time in Harry's career when he is going to say: 'I can't be a nearly man any more. We have to go one step further for me to win things in my football career.
“You don't get any younger in football and it's amazing how quickly it flies by.”
Kane, 25, put pen to paper on a new six-year contract with Spurs last summer which is due to take him through to 2024.
Honours will, however, be required if he is to cement a standing at the very top of the game and make all of his efforts worthwhile.