I mean the quintessential play it safe move was to not trade Brett Hull for Rob Ramage. I mean, Hull, had years ahead of him as a star in the league. But Cliff Fletcher thought the Flames' window was 1989. Oddly enough, the Flames had enough scoring but needed more D. The reverse if this year. And yes yes, the Flames were clearly at a different tangent on the arc. But in this era...
Think about Chicago, Toews and Kane are emerging, have huge contracts to sign coming up, so what do they do? Sign Hossa for long term to push them over the edge. Stan Bowman wasn't satisfied with maybe being a contender, he was going to make sure that the team was packed to the gills with firepower.
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