An uninspired four games against Chicago in the qualifying round doesn’t erase the positive strides the Edmonton Oilers made in the 71-game regular season. Often in hockey, a team can learn more from an embarrassing performance. No one wants a painful life lesson, but many teams have had to endure them.

A tough learning experience doesn’t guarantee a championship in the future, but I’ll be surprised if the Oilers have the same lack of gumption during their next playoff appearance.

Edmonton showed progress this season. They weren’t a Cup contender, but they were a playoff team after 71 games. And now the challenge becomes: Can they take another step, win a playoff round and become a contender?

If they do, much of it has to come internally. Sure, Holland will make a trade or sign a free agent, which will help, but to become a true contender means more growth from homegrown players.

Look at the rosters of the Stanley Cup finalists and you’ll see many key players were drafted and developed.

Tampa Bay’s roster is filled with its own draft picks, and not just first rounders.

Alex Killorn: 77th pick, 2007
Steven Stamkos: 1st pick, 2008
Victor Hedman: 2nd pick, 2009
Nikita Kucherov: 148th pick, 2011
Ondrej Palat: 208th pick, 2011
Andrei Vasilevskiy: 19th pick, 2012
Cedric Paquette: 101st pick, 2012
Brayden Point: 79th pick, 2014
Anthony Cirelli: 72nd pick, 2015

The Lightning also traded many of their drafted players or future draft picks to improve its roster.

March 2nd, 2015: Acquired Brayden Coburn for Radko Gudas (66th pick, 2010) and  2015 1st and 3rd round picks.
February 26th, 2017: Acquired Erik Cernak, Peter Budaj (no longer on team) and a 2017 7th rounder for Ben Bishop and a 2017 5th round pick.
June 15th, 2017: Acquired Mikhail Sergachev for Jonathan Drouin (3rd overall, 2013).
July 1st, 2017: Acquired Carter Verhaeghe for Kristers Gudlevskis (124th pick, 2013).
February 26th, 2018: Acquired Ryan McDonagh and JT Miller for  Vladislav Namestikov (27th pick, 2011), Brett Howden (27th pick, 2016) and Libor Hajek (37th pick, 2016). (Later they traded Miller to Vancouver for a first rounder.)
January 11th, 2019: Acquired Jan Rutta for Slater Koekkoek (10th pick, 2012).
February 20th, 2020: Acquired Blake Coleman for Nolan Foote (27th pick, 2019) and 1st rounder they acquired from Vancouver.
February 24th, 2020: Acquired Barclay Goodrow and a 2020 3rd round pick for 2020 1st round pick and Anthony Greco.

Yanni Gourde wasn’t drafted. He signed a few AHL-only deals with San Jose, before he signed one with Tampa. In 2014, Tampa signed him to a two-year ELC and he played two seasons in the AHL and got into two NHL games. He signed a one-year, two-way deal on July 25th, 2016, and played another 56 games in the minors before being recalled for the final 20 games where he scored 6-2-8. That earned him a two-year, one-way deal and he became a regular NHLer when he was 26. He scored 25 goals his rookie season and is what you’d call found money for the Lightning.

And they signed free agents Kevin Shattenkirk (one year at $1.75m), Patrick Maroon (one year, $900K), Luke Schenn (one year, $700K) and Zach Bogosian (one year, $1.3m, prorated, as he was signed on February 24th) this season to fill out their roster.

They have nine drafted players on the roster, and they traded six of their own first round picks, and one they acquired from Vancouver, to acquire other players.

The Stars have 10 of their draft picks on their roster. Four are first rounders.

Jamie Benn: 129th pick, 2007
John Klingberg: 131st pick, 2009
Jamie Oleksiak: 14th pick, 2011 (traded him to Pittsburgh, but then reacquired him).
Radek Faksa: 13th pick, 2012
Esa Lindell: 74th pick, 2012
Jason Dickinson: 29th pick, 2013
Denis Gurianov: 12th pick, 2015
Roope Hintz: 49th, 2015
Miro Heiskanen: 3rd pick, 2017
Jake Oettinger: 26th pick, 2017

Dallas did acquire a few players, but didn’t give up top picks like Tampa.

July 4th, 2013: Acquire Tyler Seguin, Rich Peverley and Ryan Button for Loui Eriksson (33rd pick, 2003), Reilly Smith (69th pick 2009), Joe Morrow and Matt Fraser.
March 1st, 2015: Acquire Mattias Janmark, Mattias Backman and a 2nd round pick (Roope Hintz) for Erik Cole and a 2015 3rd rounder (Vili Saarijarvi).
May 9th, 2017: Acquire rights to Ben Bishop for a 2017 4th round pick ( Markus Philips). Stars signed Bishop to a six-year contract three days later. I’d argue this was as much a UFA signing as a trade.
November 10th, 2018: Acquire Taylor Fedun for a 2020 7th round pick.
January 14th, 2019: Acquire Andrew Cogliano for Devin Shore (61st pick, 2012).

Outside of Seguin, their bigger acquisitions came via free agency.

Alexander Radulov signed a five-year deal ($6.25m AAV) on July 3rd, 2017
Anton Khudobin signed a two-year deal ($2.5m AAV) on July 1st, 2018.
Blake Comeau signed a three-year deal ($2.5m AAV) on July 1st, 2018.
Joe Pavelski signed a three-year deal ($7m AAV) on July 1st, 2019.
Andrej Sekera signed a one-year deal ($2m AAV) on July 1st, 2019
Corey Perry signed a one-year deal ($1.5 AAV, with $1.75m in potential bonuses) on July 1st, 2019.

Joel Kirivanta signed a two-year ELC deal ($925K AAV) on May 19th, 2019. He played mainly in the AHL this season. He did play 11 regular season NHL games, and came to the bubble as the 13th or 14th forward, but an injury to Andrew Cogliano (which rarely happens) gave him a chance to play and he produced. He scored a hat trick in game seven to defeat Colorado and he has five goals in 11 playoff games. He’s been an unexpected find.

Dallas has 10 homegrown draft picks on its roster, and Tampa Bay has nine. Many of them are key players. The 2019 Stanley Cup winning St. Louis Blues had 12, while the 2018 champion Washington Capitals had 11. Boston, runner up last season, had nine, and Vegas was an expansion team so they had none in 2018.

When Tampa wins (I expect them to win) it will be 12 years after drafting Steven Stamkos first overall and 11 years since Victor Hedman went second. That is more the norm, compared to when Chicago won in Patrick Kane and Jonathon Toews’ third seasons, and Pittsburgh won in Sidney Crosby’s fourth and Evgeni Malkin’s third. I hear more about teams needing to win during the ELC of superstars, and outside of those two teams, it often isn’t the case. It would be great, but it is rare.

The Oilers have two Hart, Ted Lindsay and Art Ross trophy winners in Connor McDavid and Leon Draisaitl. They are entering their sixth full NHL seasons. The key for the Oilers is they need the playoffs to become a regular occurrence, and I think they have the talent to do that. Can they win consistently? That is a more difficult ask.

Stamkos and Hedman didn’t have instant success either. Stamkos missed the playoffs in four of his first five seasons, while Hedman missed three of his first four.

In 2014 they lost four straight to Montreal.
In 2015 they lost the Cup Final to Chicago.
In 2016 they lost the Eastern Conference final in seven games, after leading the series 3-2.
They missed the playoffs in 2017.
In 2018 they lost the Eastern Conference final in seven games, after leading the series 3-2.
Despite having the best record in the NHL they were swept four straight in the first round in 2019.

The road to the Stanley Cup is rarely easy. Chicago and Pittsburgh were the outliers as they had pretty instant success.

Draisaitl and McDavid have made the 16-team playoffs once in their career. They made the qualifying round this year, and suffered a disappointing loss to Chicago. It should be a learning experience.

But do the Oilers have the organizational depth to fill out the roster?

Here are their current draft picks on the roster.

Ryan Nugent-Hopkins: 1st pick, 2011
Oscar Klefbom: 19th pick, 2011
Jujhar Khaira: 63rd pick, 2012
Darnell Nurse: 7th pick, 2013
Leon Draisaitl: 3rd pick, 2014
Connor McDavid: 1st pick, 2015
Caleb Jones: 117th pick, 2015
Ethan Bear: 124th pick, 2015
Kailer Yamamoto: 22nd pick, 2017

William Lagesson (91st pick, 2014), Tyler Benson (32nd pick, 2016) played eight and seven games this season. How big a part of the future they become remains to be seen.

The Oilers also have Jesse Puljujarvi (4th pick, 2016), Stuart Skinner (78th pick, 2017), Dmitri Samorukov (84th pick, 2017), Evan Bouchard (10th pick, 2018), Ryan McLeod (40th pick, 2018), Olivier Rodrigue (62nd pick, 2018), Philip Broberg (8th pick, 2019), Raphael Lavoie (38th pick, 2019) and Ilya Konovalov (85th pick, 2019).

Puljujarvi played parts of three seasons in the NHL, but was rushed and needed to regain his confidence in Finland last year and is still playing there now. He will be an NHLer, but I’m still not sure how high up the lineup he will play. He could be a top-six, or a very good third liner, but will he play in Edmonton this coming season?

I’d also say don’t sleep on defenceman Philip Kemp (208th pick, 2017). This is his fourth season at Yale, and he has taken big strides the past few seasons. Could be like Matt Benning and step out of College right into the NHL? Kemp is 6’3, 205 pounds, shoots right and is mobile. He is a wildcard.

All of these picks won’t play in Edmonton. Some might not even play in the NHL.

As the Oilers move forward, however, some of them will need to emerge and either play in Edmonton, or continue to develop and be used as trading chips to acquire other players.

Tampa wasn’t afraid to trade some of their top prospects and young players for established NHL players. A few years ago many draft pundits said they had some really good prospects and they’d all play. Well, three years later, Mitchell Stephens, Mathieu Joseph, Boris Katchouk, Taylor Raddysh are still battling to try and get in the lineup. Stephens dressed in 38 regular season games and seven in the playoffs, and when the Lighting move out one, possibly two, of Killhorn, Johnson, Palat or Gourde due to salary cap constraints, Stephens and the rest might get more of an opportunity.

When I look at the Oilers prospects, there is still some concern about top-six forwards. I think Benson and McLeod could be solid bottom six players, but I’m not sold either will be a scorer in the NHL. Lavoie has the best chance to be a scorer. He can really shoot the puck, but he needs some seasoning in the minors first. Playing in Sweden should help him.

Edmonton will need two of their forward draft picks to emerge, or Holland might have to trade some of his young D prospects to land a forward. What Edmonton desperately needs is more skill on their third line. It is a must for them to become a contender. And right now, maybe Puljujarvi is the best option to bring that. Cup winning teams usually have a third line that is almost as good as their second line.

Yanni Gourde on the third line is great for Tampa. Tyler Bozak was excellent for St.Louis in 2018. Lars Eller produced big time for the Capitals in 2017. Phil Kessel in 2016 was on the Penguins third line with Nick Bonino and they crushed hit. The Oilers need to improve their third line, add some more grit in the lineup and add a puck mover on the blueliner.

Whatever happens in the next few seasons, Oilersnation should expect that some of these draft picks get traded. They won’t all be playing in Edmonton.