Neil B made an excellent comment in OffThePostComic's post comment thread that really hit home as far as Jim Benning trading away 2nd round picks and how those picks are generally overrated. I'll just paste it right here and let you guys digest it:
We can see that JIM Benning is taking advantage of an inefficiency in the marketplace to improve the team.
Here’s the facts behind the hubub: the best pick that Benning has traded away to date was #33, this year. According to Scott Cullen’s excellent look at draft picks & future production, #33 is somewhere around a 13% chance of producing a top-6 F, a top-4 D, or a starting goaltender. The pick, historically, has an 84% chance of being a regular 4th liner, 7th defenceman, or spot goalie—or worse. Barely over 1 in 3 players picked at this spot (34%) will play 100 games in the NHL, almost all as replacement-level players. Yet, most GMs are willing to trade away a 3rd liner/4-6 D for a second round pick, when there is an 84% likelihood that the guy they choose in return will be worse than the guy they gave up, to get a chance for that 13%. "You can’t win if you don’t buy a ticket".
Therefore, second-round picks are over-valued.
In the specific trade, the draft picks that Benning traded were a 2nd and a 4th for a 3rd. Travis Yost took an interesting look at values of combined picks. From his work, we can see that the combined likelihood that Florida gets one player out of the deal that will play as many games in the NHL in their career as McCann has already played is just under 60%. There is twice the likelihood that the only NHL player that Florida received in this trade was McCann as the likelihood that either of the players picks plays 100 games at a second-line, or better, level.
Marketplace inefficiency; multiple draft picks are over-valued.
If you can trade lottery tickets that are highly unlikely to pan out for a proven NHL player with a statistically-proven floor that is higher than the likeliest value of the draft pick, then you are winning the trade. If you can see other marketplace inefficiencies (an over-reliance on statistical models that stats analysts admit do not correctly account for usage and the effect of teammates on the statistical models, just to pull an example out of a hat) while simultaneously exploiting the over-valuation of draft picks outside the first round, you stand a very high likelihood of "winning" the trade.
Well said, Neil, and thanks for doing all that homework on the stats. Very interesting.