My friend and I made a bet back in 2017 that we renew annually. Each year, I bet $2 that the Seattle Mariners won’t make the playoffs, and he bets $2 that the Seattle Sounders won’t make it to the Western Conference finals. It’s an interesting one because we both are Seattle natives, so the ideal scenario is a wash - the Mariners make it to the playoffs (-$2), and the Sounders make it to the Conference finals (+$2). On paper, the odds look like they are extremely against me. When you look more closely though, the Mariners haven’t made the playoffs in 19 years and the Sounders have made it to the Western Conference finals four times in the last five years.
As of 2020 I’m +$12. 2018 is the only year we went even, and it was because the Mariners didn’t make playoffs (+$2) and the Sounders didn’t make the Western Conference finals (-$2). This was, unfortunately, the worst result we could have hoped for.
We both hope the best case scenario happens someday. Maybe 2021.