The England international is one of the best forwards in the world, and one can see him playing for any of the world's elite clubs and contributing to their success.
Kane, on the other hand, has yet to win a trophy with Spurs, and Sherwood, speaking exclusively to Ladbrokes at the launch of the 5-A-Side bet on Arsenal against Spurs, confesses he understands why the 28-year-old sought to push his way out over the summer.
Kane's form hasn't been fantastic so far this season, and Tottenham's decision to pass up the opportunity to gain so much money from his sale is beginning to appear dubious.
Sherwood acknowledges that Tottenham CEO Daniel Levy made a difficult decision, and wonders whether the club is now questioning if they made the right one.
“Really, you're taking a chance. He'll be 28/29 by this time next year, and he won't be worth the money they turned down from Man City, so Daniel Levy had to make a difficult financial decision.