It's tough to go purely by decade on this one, because there was a group of quality middleweights who emerged in the late 80's when Hagler was on the downside and looking for the big payout with Leonard.
Hagler was like a Duran in reverse. Duran was best as LW, an ATG, but it was an average era for LWs. He needed to move up for big money fights. It was the golden age of WW's, then he had great fights at MW. Hagler was in an average era for MW's. He totally cleaned out the division, but in the early 80's, you had Hagler, Minter, Antuofermo, Hamsho, and Obelmeijas. He crushed all of them. There were no big fights waiting at 175, and he had to wait for big names to move up to him.
Top to bottom, the MW division was much better in the late 1980's. From 87-90, you had McCallum, Barkley, Kalembay, Mike Nunn, Julian Jackson, and Herol Graham around their primes. Hearns and Duran were past their best, but they were still competitive. Eubank, Collins, Benn, and Watson were starting to emerge. None of them were as good as prime Hagler, but the division was very deep in terms of fighters who were proper Middleweights/SMWs and older greats who were re-established at higher weights.
Of the fights you mentioned:
Roy Jones would have made minced meat out of the MW/SMW version of Ray Leonard, and Ray would have never taken the fight in a million years.
Prime Hagler, the Hagler that could moved, countered, and had great defense DESTROYS McClellan.
Duran 1989 and Eubank would have been fun and very close. Duran 1983 would have given him a lot of trouble, but it would still be fun.
Benn would have a punchers chance against Hearns, but I would expect Hearns to spark Benn pretty quickly.
Imaginary Dream fights:
Nunn against Roy Jones
Hagler against McCallum, Benn, and Eubank.
Julian Jackson against Hearns (spark or get sparked)
McCallum against Eubank and/or Benn
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