[Henry17]

Bets between friends often are related to teams. For example I have friends who are Cowboy or Leaf fans who make fun bets vs other team supporters. That is different. This is someone trying to make money betting having his brother bet against his ability to do so.

The way I see it this is like making a prob bet that your brother will fail at something.

If the brother was up for a promotion / getting married / going to university and you could get action that he would fail at this (and had good reason to suspect he would) would it hurt his feelings if he found out you bet against him? I think for most people they would be very hurt.