You need to get this in either local Co-op or an online game, since you have to be behind someone before the Jack Attack starts to get this. Just get enough points in the Jack Attack to come in first at the end of the round.
If you think you need to boost this, you could just log in on a second controller in local co-op, play on that controller until you get like $300 or whatever. Then when the Jack Attack starts, switch to your main controller and win.
This is way more fun legit playing with other people because not only does the achievement pop, but you can also say "Yeah, in your FACE!" which is exactly what I did. :)