The thing with those 90's trades is that unless you are as old or older than myself which is mid 40's you might not appreciate just how different economics and demographics played into this sort of thing.
First off players were not the full time athletes they are today, so to think guys who were 33 were going to keep up a high level of play was generally not common. Likley GM's didn't realize that they were at the backend of the Baby Boom that occurred from 1947 to 1966 and had peaked in 1960. Basically for about 15 years there had a been an abnormally abundant supply of young players to supplant veteran players which largely resulted in the NHL being a younger league. Which is a main reason why the era was so high scoring. Lot's of teams making the playoffs, and a lot of younger players who did not have a lot of NHL coaching, so more prone to make mistakes.
This had also been supplemented with talent coming in from Europe mostly Finland and Sweden in the 70's and 80's. The early to mid 90's saw a surge of Eastern European players come over that previously had not been available, that helped keep up the idea that there was abundant talent coming to supplant the known veterans. But with expansion and shortly after Eastern Europe had opened up, the league started to get older as the previous supply of young players was just not there, and no more hidden markets to pull players from. So deals and habits of the early to mid 80's that had paid off, didn't have the same effect. Hence trades like Mullen and MaCrimmon both made by Cliff Fletcher. Even a guy like Macoun ended up playing a lot longer than what Fletcher or Risebrough ever would have thought.
Than there is the economic aspect where players really were owned by the teams who held there rights. Free Agency was non existent. The NFL went thru a couple of labour disputes in the 80's to achieve some form of free agency. The NHL was late to follow suit, but around the early 90's people are starting to figure out Allan Eagleson and players slowly start to get some rights, and salary's start to move upwards.
When you look at the difference of Gilmour getting 625 vs 400 today, it looks laughable. But in those days it would be like Mangipane going to arbitration and the Flames thinking he's going to be awarded about 5 million, and than he gets 8.5 from the arbitrator. So if that happened today, that would absolutely shock a team.
Thru the late 80's as Oil Prices came up and the Canadian dollar strengthened the Flames were able to outmuscle teams and buy talent to supplement their drafting. But when Oil fell off after the Gulf War, and the Canadian dollar went into a nose dive at a time when NHL salary's were increasing at a rate that was unthinkable. It can't be stressed enough how hard this was on the Canadian teams at the time. Go back to 1988 what was an Engineer making, like 45k a year, which is about 1/4 of what an average hockey player was making. Lots of Engineers on this board...are you guys making 1/4 or the 3.5 million dollar salary of the average hockey player?
So when you take a lot of that into account, yes a lot of poor deals. But also pretty tricky conditions to try and wade thru as well.
Still even with all that...Gary Leeman...
