Losing a lot of games, losing a draft pick for failing to disclose a no trade list and losing a top prospect for half a season for sports betting. Ottawa Senators owner Eugene Melnyk coined the phrase in 2019 when he claimed his club was primed for a 5 year run of "unparalleled success". His bold statement ended up being quit prescient, as the Senators would indeed go on to lose many games, lose a draft pick for failing to disclose a no trade list and lost a top prospect to a sports betting suspension.
It was so embarrassing for Eugene when he had to change after having unparalleled success in his pants.