Ken Holland’s goal since arriving in Edmonton has been to ice a competitive roster while also building a strong farm system.

While he’s traded away second- and third-round draft picks and young defenders in William Lagesson, Caleb Jones, and Ethan Bear, Holland has held on tight to his first-round draft picks and prospects. As a result, the Oilers have a pretty good system, with a nice blend of quality young players who can provide NHL depth and highly-skilled prospects with upside.

After reaching the Conference Finals this spring, there will be pressure for Holland to move away from the conservative, big-picture approach and make a win-now push. Unlike last summer, Holland doesn’t have the salary cap room to make a big splash in free agency, so making a move to push this team over the top might require moving a first-round pick or a top prospect.

In the meantime, the Oilers will head into the 2022 NHL draft in Montreal in a couple of weeks with one selection in the top 100. Let’s go through the team’s farm system and try to determine what Holland might do with the No. 29 overall pick.

The Oilers graduated a handful of prospects to the big leagues last season and a few others will also be departing the organization but there’s an exciting group of players turning pro to replace them.

Evan Bouchard and Ryan McLeod have established themselves as NHLers, Philip Broberg and Stuart Skinner are right on the cusp, and Markus Niemelianen proved to be a capable call-up defenceman. Ostap Safin, Filip Berglund, and Ilya Konovalov have inked deals in Europe and Cooper Marody is an unrestricted free agent and will surely look for an opportunity elsewhere.

Filling their spots will be Xavier Bourgault, the team’s first-round pick from the 2021 draft, and a pair of players from the 2020 draft who appear to be late-round gems, Carter Savoie and Tyler Tullio.

This has become the area of strength for the Oilers, which represents a major shift from a couple of years ago when the system didn’t feature any game-changing forwards.

The Oilers used their most recent first-round draft picks on Dylan Holloway and Xavier Bourgault, a pair of forwards whose birthdays had them narrowly miss out on being eligible for the previous year’s draft. This was by design, as Holland wanted to select older forwards in the first round who could quickly make the jump to the NHL and contribute to the team on entry-level contracts.

Holloway might start the 2022-23 season in the AHL but it’s unlikely that he’ll be there for long. Depending on how the Evander Kane situation works out, the Oilers might need a big guy who skates well to play alongside Connor McDavid and Holloway fits the profile.

Bourgault will likely spend the entirety of the season with the Bakersfield Condors. It would be surprising to see him get a look before Raphael Lavoie does. Lavoie was the team’s second-round pick in the 2019 draft and has 18 goals and 36 points in 75 AHL games across two seasons.

There will be plenty of competition for playing time on the Condors, as the team will be adding an influx of young talent in the fall. A couple of late-round picks from the 2020 draft who appear to be hidden gems, Tyler Tullio and Carter Savoie, will be turning pro, and Matvei Petrov, who finished ninth in OHL scoring this season, might be joining them depending on whether the OHL opts to ban Russian players.

Evan Bouchard emerged as a top-four defender in his first full season in the NHL in 2021-22 and Philip Broberg will likely be used in a major role by the Oilers next season. After those two, the Oilers don’t have any impact defenders in their farm system.

Dmitri Samorukov would be the next name in line, but his status as an impact prospect has dropped off due to a combination of injuries and low production at the professional level. Samorukov is waiver-eligible next season, so he might wind up in the William Lagesson role as the defender who spends a lot of time in the pressbox.

Otherwise, when it comes to defencemen, Edmonton’s farm system consists of solid bottom-pairing depth types, like Phil Kemp and Mike Kesselring, and long-range projects nowhere near contributing at the NHL level, like Luca Munzenberger. This might be an area of priority for the Oilers at the draft.

Holland opted not to use the first-round pick on highly-touted goaltender Jesper Wallstedt, instead opting to trade down and go with a forward who could reach the NHL sooner. Time will tell if this was the right move but, at the very least, the Oilers have a goaltending prospect who appears to be ready.

Stuart Skinner was impressive in his rookie season in 2021-22 while Mike Smith was injured. He posted a 0.913 save percentage in 13 games with the Oilers and a 0.920 save percentage while playing in the AHL. Skinner will either be forming a tandem with Smith or another veteran if the 40-year-old retires or goes on the LTIR.

While Skinner seized the opportunity, Edmonton’s other two goaltending prospects have fallen off. Ilya Konovalov came overseas to join the Condors last season and is now heading back to the KHL after a mediocre showing in the AHL. Olivier Rodrigue, a second-round pick from the 2018 draft that the old regime traded up to select, had a 0.886 save percentage in the AHL and a 0.907 save percentage in the ECHL last season.

The most exciting prospect might be Ryan Fanti, an NCAA free agent the team signed back in March. Fanti put up a 0.929 save percentage in 37 games for the University of Minnesota-Duluth in 2021-22. He’ll likely start in the ECHL while Rodrigue splits the Condors’ net with an NHL third-string veteran type.

The Oilers are coming into this summer’s draft with their latest first selection in over a decade and without a second-, third-, or fourth-round pick.

This will likely wind up being the first time in his tenure with the Oilers that Holland trades the team’s first-round pick. Given Edmonton’s second selection in the draft after No. 29 overall will come in the fifth round, it’s fair to assume Holland will look to trade down and stockpile some more picks in the middle rounds. That’s what happened last year, as Holland traded the No. 20 overall pick to the Minnesota Wild for the No. 22 and No. 90 overall picks.

Having a couple of darts in the second or third round would be ideal for the Oilers given their current situation. They could use one to fulfill their organizational need for a defenceman or goaltender with upside and they could use the other to continue the trend of drafting forwards who can quickly contribute at the NHL level.

What’ll be interesting to see is what Holland does with the 2023 first-round pick. As I mentioned earlier, the Oilers don’t have the cap space this summer to make a handful of major free-agent additions, so doing so will more than likely need to come through trade.

Holland has hung on tight to his first-round picks so far in his tenure with the Oilers, but the pressure to win is higher now that the team has reached the Conference Finals. Whether it’s this summer or at next year’s trade deadline, he should be ready to deal the 2023 first-round pick in a trade to push the Oilers over the top.

The Oilers have built up enough depth at all levels of their system to withstand making a win-now push.