Stan Bowman’s BIGGEST Mistakes: Re-Evaluating the 2025-26 Edmonton Oilers Offseason

Did the Edmonton Oilers value sentimentality and continuity over actually winning a Stanley Cup? Welcome back to another Monday edition of Locked On Oilers! In today’s episode, host Nick Zararis steps into the "Hindsight Machine" to travel back to the summer of 2025 and deeply re-evaluate the critical front-office decisions that shaped the 2025-2026 Edmonton Oilers season. Coming off back-to-back Stanley Cup Final appearances in 2024 and 2025, General Manager Stan Bowman and the front office faced massive leverage points. Did they push the ball forward, or did they fall into the trap of overvaluing familiar faces? We break down the massive financial commitments that are now acting as net negatives on the cap—including the 8-year extension for Trent Frederick, Jake Walman's hefty contract, and how the team managed the fallout of losing Evander Kane's grit. Plus, we look at the goaltending tandem of Stuart Skinner and Calvin Pickard and wonder: What if the Oilers had signed Alex Lyon on Day 1 of free agency instead? As the 2026 NHL Free Agency and trade window looms on the horizon this July, what core thesis and lessons must Jeff Jackson, Stan Bowman, and Kris Knoblauch apply to elevate this roster to the next level? 04:46 Oilers' struggle with nostalgia 07:46 Decision-making in sports negotiations 10:39 Lockdown Oilers offseason chat 15:16 Oilers sign Trent Frederic 19:06 Discussing recent player contract evaluations 22:04 Oilers' lineup challenges in 2024 25:47 Evaluating Oilers' goaltending decisions 28:05 Oilers' questionable contract decisions Stan Bowman’s BIGGEST Mistakes: Re-Evaluating the 2025-26 Edmonton Oilers Offseason Everydayer ClubIf you never miss an episode, it’s time to make it official. Join the Locked On Everydayer Club and get ad-free audio, access to our members-only Discord, and more — all built for our most loyal fans. Click here to learn more and join your team’s community: https://lockedonpodcasts.com/everydayerclub Support Us By Supporting Our Sponsors! Indeed Now, you can speed up your hiring process with a $75 Sponsored Job Credit. Just go to https://indeed.com/podcast right now and support our show by saying you heard about Indeed on this podcast. Terms and conditions apply. KALSHI For a limited time, download the Kalshi app and use code LOCKEDON to get ten dollars when you trade ten. Kalshi. Trade on anything. Gametime Download the Gametime app, create an account, and use code LOCKEDON for $20 off your first purchase. Terms apply. Download Gametime today. What time is it? Gametime. FanDuel Today's episode is brought to you by FanDuel. From the opening whistle to the final kick, Let There Be Goals on FanDuel.Visithttps://FANDUEL.COMto get started now. 5-Hour ENERGY Get candy-flavored chaos with Fruity Rainbow 5-hour ENERGY®️ Shots - available online at https://5hourENERGY.com or Amazon FANDUEL DISCLAIMER: 21+ in select states. First online real money wager only. Bonus issued as nonwithdrawable free bets that expires in 14 days. Restrictions apply. See terms at sportsbook.fanduel.com. Gambling Problem? Call 1-800-GAMBLER or visit FanDuel.com/RG (CO, IA, MD, MI, NJ, PA, IL, VA, WV), 1-800-NEXT-STEP or text NEXTSTEP to 53342 (AZ), 1-888-789-7777 or visit ccpg.org/chat (CT), 1-800-9-WITH-IT (IN), 1-800-522-4700 (WY, KS) or visit ksgamblinghelp.com (KS), 1-877-770-STOP (LA), 1-877-8-HOPENY or text HOPENY (467369) (NY), TN REDLINE 1-800-889-9789 (TN) Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.