Drafting a Stanley Cup Contender

Introduction

Thirteen of the most recent 16 Stanley Cup winners share a common origin story: they created their teams using at least three picks that fell within the Top-5 picks of NHL entry drafts (we'll refer to these picks as T5 picks for brevity). Some of these teams nurtured all of these T5 picks into players who eventually lifted the Cup; some of these teams traded a player selected with a T5 pick for an asset that led to a Cup victory; and some of these teams saw a T5 pick fail to reach the NHL. The particulars don't seem to be very important. Instead, the necessary (but not sufficient) element to success is simply to start with the three lottery tickets.

Below, we'll briefly describe each Cup-winning team's T5 draft history leading up to their Cup victories. Take note of the three teams that won Cups without the benefit of three T5 picks; it is clear that the T5 approach is not the only way to win a Stanley Cup. Also, be aware of the teams who have drafted three (or more) players with T5 picks and (as of yet) have failed to win a Stanley Cup. Bad luck, and probably more importantly, bad management can destroy the process before it has time to succeed.

Stanley Cup Winners: 2009 - present

In the table below, the "Year" refers to the calendar year in which the team won the Stanley Cup (e.g., the Florida Panthers' "Year" is 2024 for the 2023-2024 season). The "Time to Cup" is displayed as two numbers: (1) the number of seasons between the first T5 draft pick selection and the Cup victory and (2) the number of seasons between the final T5 draft pick selection and the Cup victory. Interestingly, in all but a single case (Colorado Avalanche - 2022), the difference between these numbers is limited to five years. Thus, a natural window of five years to secure your three T5 picks is the ideal situation for a team looking to build a contender. Picks are listed in the following format: First Initial Last Name (Pick Number - Draft Year). A pick that requires further commentary will be shown with a roman numeral at the end.

[i] - Ryan Whitney was traded in February of 2009 to the Anaheim Ducks in exchange for Chris Kunitz and Eric Tangradi. Kunitz would play an integral role on the three, Cup-winning Penguins teams in 2009, 2016, and 2017.

[ii] - Cam Barker was traded in February of 2010 to the Minnesota Wild in exchange for Nick Leddy and Kim Johnsson. Leddy would play an integral role on the three, Cup-winning Blackhawks teams in 2010, 2013, and 2015.

[iii] - Phil Kessel was traded to the Toronto Maple Leafs in exchange for a 2010 first-round pick, a 2010 second-round pick, and a 2011 first-round pick. The first-round pick in 2010 was Tyler Seguin.

[iv] - Thomas Hickey never played a game at the NHL level for the Los Angeles Kings.

[v] - Brayden Schenn was traded in June of 2011 to the Philadelphia Flyers, along with Wayne Simmonds, in exchange for Mike Richards. Richards would play an integral role on the two, Cup-winning Kings teams in 2012 and 2014.

[vi] - Jordan Staal, who had already won a Cup with the 2009 Pittsburgh Penguins, was traded in June of 2012 to the Carolina Hurricanes in exchange for Brandon Sutter, Brian Dumoulin and a 2012 first-round draft pick. Sutter would later be flipped, along with a 2016 third round pick, to the Vancouver Canucks in exchange for Nick Bonino, Adam Clendening, and a 2016 second-round draft pick. Both Dumoulin and Bonino would play integral roles on the Cup-winning Penguins teams in 2016 and 2017.

[vii] - Karl Alzner left the Washington Capitals as a free agent in the Summer of 2017 (one season shy of winning a Cup).

[viii] - Jonathan Drouin was traded in June of 2017 to the Montreal Canadiens in exchange for Mikhail Sergachev (the deal involved a swap of conditional draft picks). Sergachev would play an integral role on the two, Cup-winning Lightning teams in 2020 and 2021.

[ix] - Matt Duchene was traded in November of 2017 to the Ottawa Senators in a three-way deal that saw the Colorado Avalanche receive Sam Girard in return (as well as Vladislav Kamenev and a 2018 second-round draft pick). Girard suffered a (season-ending) broken sternum in the second round of the 2022 playoffs during the Cup run for the Avalanche.

[x] - Erik Gudbranson was traded in May of 2016 to the Vancouver Canucks, along with a 2016 fifth-round draft pick, in exchange for Jared McCann and two draft picks in 2016. McCann was later traded to the Pittsburgh Penguins in 2019 for pieces that were long gone before Florida's Cup win.

[xi] - Jonathan Huberdeau was traded in July of 2022 to the Calgary Flames, along with MacKenzie Weegar, Cole Schwindt, and a 2025 first-round draft pick, in exchange for Matthew Tkachuk and a 2025 fourth-round draft pick. Tkachuk would play an integral role on the Cup-winning Panthers team in 2024.

Active T5 Strategies

Below, we list the teams that have made at least three T5 picks with the most recent pick landing within the past 10 years. We've also listed the New York Islanders as an example of a T5 approach that can be considered failed. We've dropped the "Year" column for obvious reasons and "Time to Cup" has been replaced with "Time Elapsed." In some cases, an argument can be made that the approach has failed and the "Time Elapsed" numbers may be a reasonable guide for that distinction; recall the note from the introduction about the importance of making these T5 picks within a five-year window. We have opted to list these teams in descending order of years since most recent T5 pick. Thus, if you're making short-term bets on potential Cup winners, focus on the teams listed at the top; if you prefer long-term bets on Cup winners (such as our own projections for the Florida Panthers and Edmonton Oilers from 2018), focus on the teams listed at the bottom.

Below the table, we'll post some brief remarks about each team.

New York Islanders - this is an example of a failed T5 approach. Losing John Tavares (as a UFA) for no return at all was a catastrophic mistake. Nino Niederreiter was traded at age 20 for Cal Clutterbuck. Ryan Strome was traded, six years in, for Jordan Eberle (Eberle would later be left unprotected in the 2021 expansion draft -- Seattle selected him). Griffin Reinhart was traded to the Edmonton Oilers in 2015 (having played just eight games at the NHL level). The trade netted the Islanders a first-round pick which they used to draft Mathew Barzal. Michael Dal Colle appeared in 112 games for the Islanders before leaving for Europe as a UFA. Essentially, the sum of these five T5 picks resulted in Barzal and Clutterbuck. This is a masterclass in asset mismanagement.

Edmonton Oilers - the Oilers' hopes for a Stanley Cup remain alive because they had six lottery tickets. Two of those lottery tickets (Nail Yakupov and Jesse Puljujarvi) were big swings and misses (although the Yakupov trade to St. Louis yielded the draft pick that Edmonton used on Stuart Skinner). Taylor Hall (definitely not a miss) was traded to New Jersey (in June of 2016) for Adam Larsson; alas, Larsson would be left unprotected in the expansion draft of 2021 (and selected by the Seattle Kraken). The Oilers still hold the results of three lottery tickets that saw them come within a single win of bringing home the Stanley Cup in 2024. Stay tuned.

Toronto Maple Leafs - this window remains open, but a single playoff series victory in eight years is uninspiring.

Carolina Hurricanes - this T5 approach appears to have failed. Both Elias Lindholm and Noah Hanifin were traded to the Calgary Flames in 2018 in exchange for Dougie Hamilton, Micheal Ferland, and the rights to Adam Fox. Both Hamilton (2021) and Ferland (2019) walked as free agents. Fox's rights were dealt to the New York Rangers for two second-round draft picks. Andrei Svechnikov remains the only lottery ticket left (or notable assets derived therefrom). One could make an argument that the successful offer sheet for Jesperi Kotkaniemi resulted in Carolina capturing another lottery ticket (3 - 2018), but that still leaves Carolina with just two.

Ottawa Senators - the Senators have a seven-year run of failing to qualify for the playoffs, but this T5 approach is still young (and the Senators got themselves a goalie).

Buffalo Sabres - within a four-month window in 2021, the Sabres traded away both Sam Reinhart and Jack Eichel (in the same window, they also moved on from their 8th overall pick in 2013 - Rasmus Ristolainen). Instead of adding Owen Power to Reinhart, Eichel, and Rasmus Dahlin, the Sabres added Power to Devon Levi, Alex Tuch, and Dahlin. The Reinhart and Eichel trades also netted Buffalo two (bottom-half) first-round picks in Noah Ostlund and Jiri Kulich. The Sabres got impatient with three T5 picks in hand (and one more coming that Summer) and decided to blow it up.

Utah Utahs - these three T5 picks are spread out over seven years instead of the expected five-year window. I added Utah to this list anyway to mention that new ownership probably did the team a disservice by going heavy on free agents this past Summer. Utah really could have used another top pick here to set them up for the future. Note: Dylan Strome was traded to Chicago in November of 2018 for Nick Schmaltz.

New Jersey Devils - the Devils are in a great spot here with four T5 picks in a narrow range of time. Their window is wide open and they could take a few shots in the coming years.

Columbus Blue Jackets - you may recall that Pierre-Luc Dubois was traded to the Winnipeg Jets in January of 2021 in exchange for Patrik Laine and Jack Roslovic. Neither Laine nor Roslovic are with Columbus any longer; Jordan Harris and a couple of 2026 picks are all that remain. But Columbus' future remains bright as they hold three lottery tickets spent over the course of the past four Summers.

Montreal Canadiens - the Canadiens are likely to be rewarded down the road for landing three consecutive T5 picks. As always, patience will be the key since history tells us it takes 3-10 years after the final T5 pick to compete for the Cup. Will the additions of Patrik Laine and a healthy Kirby Dach prevent Montreal from landing a fourth T5 pick next Summer?

Chicago Blackhawks - the Blackhawks seem to be on the right track with back-to-back T5 picks in the two most recent Summers. They added some free agents this Summer (and will benefit from a healthy Taylor Hall). A third T5 pick in Summer 2025 would be the ideal path for the Blackhawks after trading Kirby Dach two Summers ago.

Anaheim Ducks - I know, I know; the Ducks didn't draft Cutter Gauthier (but this is next best thing). Look at that beautiful list of four T5 picks in as many drafts. This is going to take some time, so settle in Ducks fans -- the future looks bright.

Teams That Need to Lose in 2024-2025

The following teams are sitting on two T5 picks and need to finish near the bottom of the standings in 2024-2025: San Jose Sharks and Seattle Kraken.

The Los Angeles Kings and New York Rangers also have two T5 picks (drafted by them) on their rosters, but it's clear that these teams are not going to finish the 2024-2025 season with a chance at a T5 pick.