I haven't used this team ability before, but I figured that I'd give it a go at my next tournament using Thunderbolts to get it. Say I have a figure that is 20 points a figure that is 30 points and a figure that is 40 points. The 20 pointer is adjacent to both the 30 and the 40, could both of these characters get the outwit as they are both adjacent to the 20 pointer?

My gut thought is yes. Because of the way the TA is worded. Any other thoughts?

Yes you have it right. All 3 in a line/circle, the 2 highest point totals would get Outwit.