One of his closest pals Rohan Ricketts - who made the move across the capital in 2002 - reckons winger Bentley can go on and become a Spurs legend just like Paul Gascoigne.
But the midfielder, who now plays in the MLS with Toronto, warns the move will not be without its dangers.
Ricketts told The Sun: "I played with David in the same Arsenal side that won the FA Youth Cup. We go back a long way and we have stayed good pals, so I'm really pleased for him that's he's signed for a big club like Tottenham.
"The fans booed me every time I touched the ball and I copped some really bad flak because the clubs are such rivals. The same will happen to David and I'm positive the Arsenal fans will get on his back.
"But at the end of the day, the club didn't want him so I'm sure he won't care. He'll just get on with his job and not let it affect him.
"I can understand why he left Arsenal because he wasn't getting regular football. He had competition from the likes of Robert Pires and Freddy Ljungberg, who were world-class.
"A player of David's quality must play first-team football and Arsenal just couldn't deliver that.
"The fans should understand that. I was in the same boat. As a young player at a club like Arsenal, they have the luxury of picking the very best and some of us had to move.
"Now he's good enough to play for Arsenal but it's their own fault for letting him go. He's just trying to broaden his horizons and better himself. There's nothing wrong with that.
"It's a great move for him because Spurs is a club with a bit more potential than Blackburn. They will be pushing for a Champions League spot, which is what a player like David Bentley needs."