I think with Florida, Tampa and Vegas the league just kinda let the LTIR situation play itself out the way it did on it's own (instead of stepping in earlier) because it served to Bettman's narrative of hockey being successful in the south. Every year another warm-weather/expansion team was benefitting from the glaring loophole that existed, all while the disaster in Arizona was rapidly unfolding (with relocation to Utah being the obvious outcome). Having Tampa, Florida and Vegas winning cups while Arizona was in full nuclear meltdown mode while playing in a 4,600 seat college rink served as a good distraction.
They didn't necessarily need to manipulate anything for those teams to have success - they just had to ignore the ever-so-obvious LTIR problem that existed (and that markets where Bettman expanded into benefitting the most by unlucky injuries). If a team like Winnipeg or Ottawa managed to win a cup by exploiting the LTIR my guess is that loophole would have been closed immediately, the team would probably have forfeited draft picks and Bettman would personally erase their cup from the record books. But because these teams were in non-traditional markets, that had existed for decades with limited success were the ones benefitting, it wasn't a problem. It wasn't a problem that teams could operate 10-18M+ over the cap in the playoffs - even though Bettman was the driving force behind the cap, parity and "cost-certainty" to begin with.
Think about this - Florida had been around a long time with just one SCF loss in 1996 & Tampa had their one cup in 2004. I'm sure Bettman was worried about the clock running out on those markets as well when Arizona was imploding. Florida's attenace was terrible leading up to Covid.
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