Bloody Brian Burke
#1 CFL Fan!
Actually the Isles had multiple top 5 picks and they just kept on sucking. However, I do agree that comments about tanking and not spending money to make a team competitive are pretty rich coming from an Isles fan.
That's why I said 15 years rather than more recent - the era from 2000-2008 in particular. They made the playoffs 4 times but never won a series and were as stuck in neutral as it gets. And after drafting Rickety, the highest draft pick they had in that span was 7th overall (Okposo). Even afterward, they only had 2 top-4 picks (JT and Reinhart) and 3 5th's (one of which turned into Cal fucking Clutterbuck). For that much suffering, that's a pretty shitty return.