Probably a lot off topic, but I'd make the argument those Pollock type deals have persisted well into recent times.
The first overall pick in 1998 originally belonged to the Florida Panthers, who traded it to San Jose for Viktor Kozlov in 1997. Somehow San Jose then ended up trading that pick to Tampa for Bryan Marchment and junk. Months later, Vincent Lecavalier...
It was an interesting trade, Phil Esposito wanted the option to swap picks with San Jose. At that point, Tampa was going to be #1 heading into the lottery. I think Florida was somewhere around #3 or #4 at the trade deadline. Sharks GM Dean Lombardi was willing to use the Florida lottery odds as an asset.
The worst case scenario was the Florida pick winning the lottery but the Sharks would still pick #2. Harder with hindsight, but in the moment most scouts didn't think David Legwand was a big drop off from Lecavalier; And perhaps the Sharks knew they were eyeing Brad Stuart like how Lombardi coveted Drew Doughty in the Steven Stamkos draft year.
Florida had made the playoffs in 1997 so they probably weren't anticipating giving up a top 5 pick for Kozlov.
Sharks also gave up their own 1998 1st to get Mike Ricci after trading away Kozlov. By some small miracle, Colorado didn't have higher picks as Pierre Lacroix went on a side quest to try to land Lecavalier.
June 1996: Traded Stephane Fiset to Los Angeles for his son Eric Lacroix and the option to swap 1998 1sts
November 1996: Traded Chris Simon and Curtis Leschyshyn to Washington for Keith Jones and 1998 1st + 4th
November 1996: Traded Landon Wilson and Anders Myrvold to Boston for 1998 1st
November 1997: Traded Mike Ricci + 1998 2nd to San Jose for Shean Donovan and 1998 1st
After that last trade, Colorado had the 1998 1sts from the teams who picked #1-2-3-9 in the 1997 Draft. All four teams ended up making the playoffs in 1998.
I thought Colorado made a risky trade in July 2011. They gave up their 2012 1st (unprotected?) to get Semyon Varlamov. Colorado was a week removed from picking Gabriel Landeskog #2. But it seemed like teams knew the 2012 class wasn't strong, so maybe Colorado took the calculated risk. Washington still had Filip Forsberg fall in their laps.
Nashville traded Tomas Vokoun in 2007 to Florida for a 2008 1st which ended up being in the top 10. Maybe more memorable if Nashville had walked out with somebody better than Colin Wilson.