The North London derby is one of the most-heated football derbies in English football and the list of players who dared to cross the rivalry is unsurprisingly small.
Two of the names everyone will likely remember are Sol Campbell and Emmanuel Adebayor, with the former's move in particular making plenty of headlines when it happened.
The centre-back had previously assured Spurs fans he would stay put, while also insisting he would never play for the Gunners, only to then commit the ultimate sin and join his boyhood's arch-rival on a free transfer.
Ouch!
Adebayor, meanwhile, seemed to make a bit of a sport out of winding up Arsenal fans at every opportunity he got after leaving the club. A true rebel!
But who else had the courage to represent both rivals? Let's take a look.