Bought a seriously expensive car.

Own at least one car each from the '60s, '70s, '80s, '90s and '00s.

Win your first B-Spec event race.

In an online game, own all the railroads and utilities

Bankrupted another player online

Acquire a car manufactured in 1959 or earlier.

Take down Castro with a headshot.

Win your first A-Spec event race.

Someone pays you rent before your second turn

Successfully won against 3 hard AI

Acquire the most expensive property in the game

Own 3 color groups at once

Completed a trade that gave another player a color group