Like most GMs, Treliving started well and ended badly. Most GMs get fired eventually, so it's only natural that they end badly. Sometimes they start off badly and never get any better: see Risebrough, Doug.
The biggest thing I fault Treliving for is his incomprehensible choices when hiring coaches. The second biggest thing is not the Gaudreau-Huberdeau mess – nobody saw either half of that coming – but the Hamonic trade.
Hamonic was a good player to acquire and filled a need, but Treliving paid far too much for him. (I think I said at the time that he ‘gave too much for his whistle’ – from Benjamin Franklin's story about giving all his pennies for a tin whistle as a boy, without asking the price first. If I didn't post it here, I certainly said it to other people.)
I still believe that the Flames thought they had a deal with Gaudreau right up to the moment when they didn't. And nobody, on CP or elsewhere, expected Huberdeau to have the single largest drop in point production in NHL history immediately after he was signed. That whole situation would make any GM look like a dunce.
Treliving definitely traded away far too many draft picks, and then lessened the impact of the picks he had left by trading down to get more volume at the expense of quality. You can't keep your farm system full if you sleep through the first two rounds of the draft year after year. He's repeated that error in Toronto, where, to be fair, they were already spending picks for questionable players under Dubas.
If I had to sum up Treliving's faults in one word, it would be impatience. He tries to reach for deals that aren't there (hence the ‘in on everything’ insult) and tends to jump on bad deals when he should stand pat (hence Neal and Brouwer as well as Hamonic).
He's not a stupid man, but he doesn't seem to have the temperament to realize that the ‘process’ he loves to talk about can't be rushed without spoiling the results. As a wise but vulgar man said, it takes a woman nine months to have a baby, no matter how many men you put on the job.
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