In a way he had opportunities but he was always the opponent and never the star. He never got his career built gearing towards the big payday. Look at his mw fights he's known best for, Nunn Sumbu, Duran, Hearns. He was the opponent in every one of them. that being said even the way he was managed he pulled it all out against hearns and that was his chance. All he had to do was overcome the fat lightweight and the big bucks with Leonard surely beckoned. However Duran had enough to turn back the clock one last time.
Barkley was a solid fighter but he was not really great and that is the problem with him not getting headline fights.. Leonard was a case where Barkley was just too unpredicatable for him to fight. You just didn't know how Barkley style would match up with guys. He was strong and had heart, but he could be beaten. Even back in 1988 he fights Kalambay and loses 15 rounds, then fights Olajide and wins after he is knocked down with a nice counter hook. Then he beat the legend Hearns and then gets beaten by another legend Duran. All unpredicatable really. Not very consistent. After Duran he loses to Nunn in a relatively close fight yet not really a threat to beat Nunn that night, and then loses to Benn in 1990 on a 3 knockdown rule. I don't know if his unpredictable style would get many headline fights. He didn't win consistently to get the headline, yet he did fight everyone. That list from 1988 to 1990 was incredible. Kalambay,Olajide,Hearns,Duran,Nunn, Benn. in two years. So I give him credit. He deserves it. Barkley would have fought Tyson or Foreman had they offered it. By the way Barkley had an interesting style. He did better at a distance from guys than up close, where he could be countered on the inside, which was his weakness. Olajide, Benn, Duran all hurt him on the inside. If you notice, Hearns fought him on the inside in the rematch since he had an easier time hitting him with the left hook inside than with the right outside. Hearns actually adjusted, but it wasn't his fight to fight like that since Barkley was bigger and stronger. But had Hearns won another 2 rounds in the fight he wins a decision in the rematch.
That is the point really, he wasn't great enough to justify the schedule he fought and he shouldn't be unfairly judged because of that. He got schooled by sumbu buy worked his way up to a good contender level and upset the odds to spark hearns. Maybe he thought Duran was a smart fight to take coz of age and weight so I can understand that but once he lost that he should gone for a rematch a Leonard fight or a vacant wbc title. Instead he consecutively fought Nunn and Benn two top ranked middleweights. He basically never got a chance to build his resume and status. Maybe that's who he was and he always wanted the tough fights but because of that he went on a big losing streak and ended up being the opponent. He never took the smart money and because of that he went broke and is broke. Now normally I don't care about this stuff but boxing is how they earn a living and someone who won belts at 3 weights and fought that many top names deserves a decent retirement. He fought close with Duran and should have waited for the vacant wbc belt where he was still the name fighter. Instead he took tough fights he just wasn't capable of winning.