He isnt unlucky. It is his job to be ambitious and seek out the best drives possible. Senna, Prost, Mansell, Piquet and every other great, has done this in the past.
Every other great?
Moss. Tried to aim for British wherever possible, which cost him dearly at times. Drove for Maserati in the first instance because he bought the actual car (in '54 when the Merc was dominating in the hands of a certain Mr Fangio). In the second instance, he was advised to drive for them (in '56, when a Ferrari was winning at the hands of a certain Mr Fangio) by the motoring press in England.
Hawthorn. Aside from his opening moments in the sport (where he drove a modified ERA if I remember right) he drove for Ferrari right up until he met his untimely end. And they weren't the best throughout.
Clark. Drove only for Lotus. And they also weren't the best throughout.
Stewart. Drove for BRM (who weren't all that good by that time) and for Ken Tyrell. Who wasn't the best throughout (though admittedly JYS getting a stomach ulcer one year didn't help matters).
Brabham. After leaving Cooper, he persisted with his own team for the '61 season. And '62. And '63. And '64. And '65. He had to wait until '66 before winning a title again. And then didn't win another until his retirement. I'm pretty sure that means that Brabham (the team)
also wasn't the best throughout.
Also, in the past, the car has always dictated who won the most races
Not always. I won't bore you with every single example - instead, I shall pick the popular one. 1982. You cannot possibly tell me that the Williams that Keke Rosberg had was better than the Ferrari (it was running a Cossie N/A motor versus the turbo of the Ferrari for a start). Ferrari only lost that year because of Didier Pironi. If he'd not played silly buggers at Imola, Gilles Villeneuve would not have crashed at Zolder and would have gone on to win the title that year.
though perhaps in 2008, the car makes even more of a difference than in the past. The key is to help develop the car to your liking and get the best out of it on race weekends. Alonso is very good at this.
Won't argue there. Also won't argue that The Petulant One™ is a good dev driver....not the best ever necessarily, but a pretty good one.
Hamilton's big test this year will come when he has to set up his car on his own, without copying a more experienced teammate's setup, as he did last year.
I don't think The Petulant One™ let The Messiah™ use much of his setup data after the opening round or two
***edit***
Regarding Hawthorn. The car he started out in was a Cooper T20 with a Bristol engine. I think the T20 started out as an ERA at some point. Or a HWM. I don't think it was the latter, but I've had several (read: lots of) beers and the memory is not entirely reliable. What I
have remembered is that he drove the odd one or two races for Vanwall and Maserati, but not many.