Despite being on the job as Edmonton Oilers general manager for just two summers, Stan Bowman stands at a crossroads as July 1, 2026, arrives.

Known as the GM of record for three Stanley Cup victories while with the Chicago Blackhawks, Bowman’s work in Chicago included some outstanding trades (acquiring Nick Leddy) and strong drafting (Brandon Saad, Teuvo Teravainen, Alex DeBrincat). However, the strength of the team he inherited meant some question marks about his ability to build a championship roster. Those questions haven’t been answered during his time in Edmonton.

In Bowman’s first full offseason with the Oilers, he added prospect winger Ike Howard via trade while signing Andrew Mangiapane and Jack Roslovic in free agency. The Mangiapane signing continued a trend of poor decisions on Day 1 of free agency by the organization stretching back to Milan Lucic in 2016. Roslovic, signed on the opening night of the 2025-26 season, was a smarter investment.

The hockey gods have been screaming at the Oilers for a decade. Will the team’s general manager listen? Bowman should wait for the market to come to him. There are signs he’s doing exactly that in the ongoing Darnell Nurse negotiations, but the true test will arrive July 1.

Possible free-agent targets

July 1 targets are the most dangerous in any year, and especially this season. A perfect storm has the cap rising precipitously, while the quantity and quality of available free agents are poor. That could spell the kind of free-agent nightmare the Oilers delivered themselves in 2016, when then GM Peter Chiarelli signed Lucic and then dealt star winger Taylor Hall in a stunning talent bleed fans still talk about to this day.

We can assume Bowman will deal Nurse, and for the purpose of our conversation, we can estimate Bowman will have $15-plus million to acquire talent. The roster, sans Nurse, would stand at 17, including 11 forwards, five defencemen and one goalie. Bowman would need to add a goaltender, two defencemen and three forwards to the group. The club would have only one strong candidate pushing from Bakersfield (Damien Carfagna) and two forwards (Quinn Hutson, Connor Clattenburg) in the conversation for opening-night roster spots.

If the team arrives at July 1 with $15-plus million to spend on six additions, Bowman should remember the lessons of Mangiapane and Roslovic and stay quiet on July 1. Using The Athletic’s free-agent big board, here are some candidates for Bowman in free agency:

PlayerPositionAgeEst AAV

LD

29

$4.37M x 4 yrs

RW

24

$4.1M (OS)

LW

26

$1.93M x 2 yrs

RD

30

$2M x 2 yrs

The lessons of Mangiapane and other July 1 signings are applied to this short, risk-averse list that is populated by just one player age 30, and none older. The Oilers already have mid-30s players on no-movement deals; Bowman needs to do himself and future general managers a favour and stop signing those deals.

In the meantime, Ryan Shea is a great bet to replace Nurse or play third pair if Jake Walman slides in on the second pair with Connor Murphy. It’s a risky move due to age, but Shea seems to be getting better every year and has the look of a defenceman who will age well.

Mavrik Bourque is a prime candidate for an offer sheet. The Oilers wouldn’t be able to pursue Bourque before a Nurse trade is completed, but could make him a free-agent target on July 1, based on PuckPedia’s reading of offer sheet windows. Bourque falls in line with Bowman’s efforts to add youth up front, currently represented by Vasily Podkzolin and Matt Savoie, with Howard ready for full-time duty this fall. Adding Bourque, a smaller skill winger, might make Savoie or Howard more available for trade.

Pavol Regenda might be the least famous free agent this summer, but he pumped in nine goals in 28 games with the San Jose Sharks this season. He’s a big forward (6-foot-4, 212 pounds), and the estimated AAV might be low, but he’s a good risk for a team like Edmonton looking for skilled forwards well under 30.

Vincent Desharnais is a big man whose wingspan makes him difficult to attack off the rush. Added to penalty-killing prowess and a legendary mean streak, he could step in and improve the Oilers in several areas.

The lesson of Roslovic

When the Oilers signed Roslovic on Oct. 8, the veteran scorer had been hanging out in free agency for months. This happens every year, and in the case of Roslovic, who scored 21 goals for Edmonton, it should result in a handsome payday this year. The Oilers should not be the team to pay him.

The play for Bowman would be waiting for other teams to overspend on mid-level free agents. At some point, the market will come back (it does every year), and Edmonton can take advantage. Signing Roslovic last year was a brilliant move; the Oilers should plan for a late summer-early fall shopping spree every year. Owner Daryl Katz would be getting far more for his free-agent dollars.

This is especially true with goaltenders. This season, free-agent goaltenders are everywhere, and there are several teams with three quality waiver-eligible goalies who will be looking to deal. Bowman shouldn’t spend a dime on a goaltender because the gap from worst to best isn’t large, and NHL teams have proven time and again they can’t predict who is about to have a strong season. The possible outcomes of high to low signings are massive and seemingly random.

If the Oilers wait until July 10 and sign Connor Ingram, it’s possible he will be the top-performing goaltender acquired in free agency this summer.

Bowman could sign Ingram, trade for an inexpensive goaltender (Michael DiPietro of the Boston Bruins is an attractive candidate) and come to camp with those two plus Tristan Jarry as options. The club could spend part of the season riding three goaltenders, eventually deciding on the tandem best suited to the team. Edmonton could take a page from the Stanley Cup champion Carolina Hurricanes and use the waiver wire to audition goalies.

The only strategy Bowman must avoid is signing a goalie to a long, free-agent deal with big dollars attached. The organization should look at its own history and the signing of Jack Campbell in 2022 as a reminder of the risk involved in long investments at the position.

Bottom line

Every day that goes by sees Oilers fans more upset that Nurse hasn’t been traded and the Oilers haven’t added to last year’s roster. The best move for Bowman? Exactly what he’s doing now. In keeping his powder dry, Bowman is letting the market come to him, in the Nurse deal and in addressing needs.

If he moves Nurse to the Bruins for DiPietro and a small retention, that gives him room to wheel in free agency and via trade. Adding Shea, Regenda and Desharnais in free agency allows the club to bring in two additional forwards via trade.

Bowman needs to change the culture of the Oilers in free agency. The Nurse deal will fall into place when it comes. The only thing Bowman will miss in waiting for the best deal is wasting money on an aging free agent with his best years long past. Surely the Oilers have had their fill of those.