The “Win Now” Fallacy

Andrew Dellapina
How to Win
Published in
3 min readJun 26, 2017
Travis Hamonic skating as a member of the New York Islanders (Courtesy: Wikipedia)

Imagine that you are a fan of a team which has been stuck in the middle third of the league standings for the past few seasons. You have a superstar center in his prime who lacks adequate linemates. You also have a stable of top four defensemen who are largely interchangeable, although they each produce in different ways. It’s been decades since your team has had sustained success but you also aren’t quite in a position where a couple of win-now moves make you a true contender.

So you make a few trades. You ship out a 23 year old forward who, in more than 250 NHL games over four seasons, has yet to have more of an impact than the average third liner. In return you get a first line scorer on a market value contract who, in the unluckiest season of his career, still would have been your fourth-leading scorer. You then trade away one of those top four defensemen, a player who is coming off of the worst season of his career and likely has decreased trade value as a result, for a first round pick and two seconds.

All in all, it sounds pretty good. You acquired a new first line forward and three high draft picks for a middling prospect and a solid defenseman without crippling that defensive strength you previously held. Unless, of course, you’re the New York Islanders, in which case everybody is suddenly clamoring about the apparent lack of “direction” and “vision”. How can a team make a move for a win-now scorer and then send off a defenseman for futures? Clearly GM Garth Snow doesn’t have a plan.

No matter whether you’re a “mainstream media traditionalist” or a “fancy stats blogger”, one of the few things people seem to agree on is that some teams need to make moves to win now and some need to rebuild for the future. I think this is a misguided notion. How many teams are truly in a win now position? You could make the argument that the Chicago Blackhawks are, which makes their decisions this weekend all the more questionable. Pittsburgh is a pretty young team outside of two generational talents who will be productive players long past a traditional prime. The New York Rangers have seemingly cheated certain death for years and continue to replace aging talent with younger options. Tampa Bay and Nashville are young teams built to contend for the long haul. There aren’t many teams who have to throw everything they have at a two-year window, regardless of what some people might like to tell you.

In fact, teams often get criticized for throwing away assets on win-now pieces, as they rightfully should. The Minnesota Wild paid nearly the exact price for rental Martin Hanzal that the Islanders received for “sell-low” Hamonic. Ultimately, Hanzal had little impact as the Wild were eliminated in the first round and Arizona now has an opportunity to turn those picks into years of cost-controlled NHL talent. If Hanzal was a member of the Wild entering the 2016–17 season and was traded away for those picks, would it be considered a bad move which contradicts the “direction” of the team? Or could it possibly be that Chuck Fletcher viewed his team sans Hanzal as a top five NHL squad (per their finish in the league standings this season) and realized he could recoup a lot of future assets for a move that would ultimately result in possibly a 1% (and that’s being generous) smaller chance of winning the Stanley Cup this season? Those draft picks could be useful in three years when the contracts of a declining Ryan Suter and Zach Parise hamstring the team’s ability to pay for high-end talent. Perhaps that first round pick could give the Wild a 5% higher chance of winning it all in 2020.

That’s a bit of a far-fetched hypothetical, to be sure, but the point stands. Any team banking on winning the Stanley Cup in a given season is being foolhardy — just ask the Washington Capitals how sure of a bet it can be. It’s not an all-or-nothing proposition; teams are capable of making moves that help them now as well as in the future. In fact, that’s probably the best approach to running a successful team year after year.

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