Rick messes up in the Prom, but the guilty one was Jerry.

I know Rick messes up the house deed by gambling, but it looks like he was automatically forced to own the tunnel in a hurry.

Jerry didn't know that the tunnel has more requirements and the worst he did was ruined Molly's prom romance with Ben in a tragic disaster at the end.

Bottom line, Jerry wanted his eccentricity in desperation, but it was too strong and he should be feeling guilty about it, no offense.