After a hot-and-cold stretch of hockey in the 1950s (3 Stanley Cup Final appearances, 3 winning records), Boston went into a brutal stretch up until Orr/Espo arrived. The first year of this stretch was after a solid 2nd place finish in 1959. Bronco Horvath had a career year where he barely missed out on the Art Ross Trophy, but their 28-34-8 record would not be good enough to make the playoffs (Detroit edged them out by 3 points)- and yet it would be their best record until 1967-68. The next 7 years: Never won more than 21 games (albeit in a 70-game schedule), never even coming close to a top 4 spot: 1961: Last place, 23 points back of 4th place Detroit 1962: Last place, 26 points back of 4th place NY Rangers 1963: Last place, 32 points back of 4th place Detroit 1964: Last place, 23 points back of 4th place Detroit 1965: Last place, 26 points back of 4th place Toronto 1966: 5th place (albeit only 1 point ahead of NY Rangers 48-47), 26 points back of 4th place Detroit 1967: Last place, 28 points back of 4th place NY Rangers In 7 years, they were only 1 point from 7 straight last place finishes! It's not like their ownership was Bruce Norris-Detroit or Harold Ballard-Toronto bad, they didn't have 1950s Blackhawks level attendance/TV ratings problems. And yet there they were, going from punching above their weight in the 1950s to not even coming close to the postseason. As bad as things were for Edmonton post-Pronger and pre-McDavid, they came close to making the postseason at one point (Only 3 points out in 2007-08, only 6 points out in 2008-09). Or Florida's 2001-2011 drought where they had a close call in 2008-09. Why did things get so bad before things got so much better with Orr and Esposito as the decade came to a close?