After Robert crashed his second Ferrari

[Bassim]

I am wondering if my sentence is grammatically correct.

After Robert crashed his second Ferrari in the same year, his father, a wealthy businessman, told him he should find a job and pay for the next car from his own pocket.

 

[Charlie Bernstein]

I am wondering if my sentence is grammatically correct.

After Robert crashed two Ferraris in one year, his father, a wealthy businessman, told him he should find a job and pay for the next car out of his own pocket.

That's how most native speakers would probably phrase it.

PS - He certainly should!

 

[PaulMatthews]

I am wondering if my sentence is grammatically correct.

After Robert crashed his second Ferrari in the same year, his father, a wealthy businessman, told him he should find a job and pay for the next car from his own pocket.

Yes it is, and it's prefectly natural too.

 

[Tarheel]

I am wondering if my sentence is grammatically correct.

After Robert crashed his second Ferrari, his father, a wealthy businessman, told him he should find a job and pay for the next car from his own pocket.

You might consider deleting "in the same year" (as I did). But leave it in if it's important to the story (and that isn't explained elsewhere).