If you think you have experienced a glitch you may want to try this: If you do not get this your first play thru try another play thru. I found that I had over 3 million dollars cumulativly and had not got the achievement, but the moment I got 1 million dollars on hand the achievement poped. Pretty much a luck of the draw achievement just as many of the others. I think if you have not gotten this with all the stated solutions here, (which are all good) your just going to have to keep re-playing the game until you get it. So I hope for your sake you really like this game!