You are the general manager of an NHL team with a promising young core, a demanding fan base, and exactly $9.2 million in cap space. What could go wrong? Let's find out.

1. You open your morning by checking your inbox. Your top pending UFA's agent wants to talk term. Do you:

A) Offer a short bridge deal to keep flexibility → Go to 2

B) Cave and offer eight years to make him happy → Go to 3

2. You offer a three-year bridge deal. The agent laughs, actually laughs, over the phone. He says his client wants "term and term only." You hang up and stare at the ceiling. A rival team swoops in and signs him for seven years the next morning. Your fan base spends the next 48 hours calling you cheap. Your other pending UFAs watch this happen and quietly start asking their agents about term.

Do you overcorrect on the next deal? → Go to 3

3. You offer eight years. He signs immediately. Everyone is thrilled. Your Twitter mentions are, for one shining afternoon, entirely positive. You feel good about yourself. You go get a coffee to celebrate.

Two years later, he's 33, his skating has fallen off a cliff, and he has a full no movement clause. You cannot bench him, trade him, or discuss him publicly without someone posting the AAV next to a crying emoji.

Do you try to move him anyway? → Go to 4

4. You call around. Nobody wants the contract. One GM laughs at you, actually laughs, the same laugh from the agent two years ago. You retain salary just to generate any interest at all. Ownership asks why you're paying a player $2 million a year to play somewhere else.

You tell them it builds character. Do you learn from this? → Go to 5

5. You swear off long-term deals entirely. From now on, three years max, no exceptions. This policy lasts exactly one offseason, until a younger core piece becomes a pending UFA and his camp wants term "or we walk."

Do you hold the line this time? → Go to 6

6. You hold the line. He walks in free agency. He thrives elsewhere. Local media runs a retrospective titled "The One That Got Away," with your photo directly under the headline. Fans start a countdown clock to the next time you're allowed to speak publicly.

Do you finally give in and pay the next guy whatever he wants? → Go to 7

7. You give the next guy whatever he wants. Eight years. Full no movement. A signing bonus so large it makes your accountant physically leave the room. He's thrilled. You're thrilled. The city is thrilled.

Two years later, you are once again on the phone with a GM who is laughing at you.

THE END.

You have reached one of this adventure's endings: Cap Hell, Eternal Loop Edition. No matter which path you chose, you are now managing a $2 million dead cap hit, a fan base with a long memory, and an agent who has your direct line memorized.

Want to try again? Go back to 1 and pick differently. Spoiler: it does not matter. Every road leads here. This is the NHL now. 

Bookmark The Hockey News Edmonton Oilers team site to never miss the latest newsgame-day coverage, and moreAdd us to your Google News favourites, and never miss a story.

Comments
anonymous profile image
Powered by RoundtableBuilt on infrastructure designed for real-time media. Learn more at RTB.io.© Roundtable 2026. By using this site you agree to the Terms of Use and Privacy Policy