For a man who has played in Holland with Ajax, Germany with Hamburg and Spain with the great Real Madrid, the move to Spurs doesn't seem to be a step in the right direction. Simply put, however, it was. Tottenham Hotspur has more to offer Rafael Van der Vaart than Real Madrid and for about eight million pounds, Madrid got screwed.
This might come as a shock to many football fans across the globe but Rafael Van der Vaart is not the best player in the world. If he were a Ronaldo or Messi type, this would be a slightly different read. But he's not. And really, he's not even close.
He isn't an earth-shattering game changer who single handedly shoulders the weight of a franchise the size of Real Madrid or Manchester United. Could he start at either of these clubs? Yes, he most certainly can. He has the ability to play for any team in the world. Some teams have players that could, perhaps, do a better job but VdV could step in and do just fine given the opportunity.
Van der Vaart did, in fact, start and play at Real Madrid despite being eventually deemed as surplus. Harry Redknapp came knocking on VdV's door at the perfect time for Rafael to mature into the player he can and should be.
In comparison to Real Madrid, the smaller clubs of Ajax and Hamburg developed VdV into a world class attacking midfielder that is an exceptional passer and finisher, has superb vision, and feeds his team mates well to create a formidable striking outfit.
The move to Madrid took Rafael to the pinnacle of professional football and was essential for his development. Eventually, when players such as VdV are completely surrounded by world class talent, the excess of this talent can stifle some players to the point that they are no longer able to contribute to the club. A move away from said club can work to break the over-talent shackles (see Raul at Shalke or Clarence Seedorf at AC Milan).
The move to Tottenham did exactly that for Van der Vaart. He's now free to spread his wings and be a major star and backbone of an entire club. This major contribution helped take Spurs to the Champions League quarter finals.
So, what do we have now? A player who gets to be a big star at a fairly big club and a team that got a great player, for cheap, that enjoys succeeding for the team.