I won this race with a level 20 Bob. He needed 4 goes at it though. You need to be lucky and get into the lead fairly early in the race, at which point you can lower the hot/cool meter to the middle - which will stop him crashing at the chicane. The Toyota 7 in clear air will romp away, briefly, but watch out - once the AI 2J clears the Ferraris, Fords, Z06 and Jaguar it will start motoring after you and you are then in a bit of a chess game of trying to keep Bob ahead but not going too hard, cos he'll crash.... tricky race.
It is worth redoing this race over and over and over - you win the 620kg Alfa, which (with a mid turbo upgrade) is an absolutely awesome thing.
Bare in mind that I used the same driver at level 19, 19, 20, 20 - the previous races I got 11th place, twice - one race to the next is totally different..... retry, retry, retry!