Here’s a hypothetical hockey scenario you won’t encounter very often: “What if the Dallas Stars didn’t drop the ball when Tyler Seguin and Jamie Benn were dirt-cheap.”

Consider this. From 2013-14 (Seguin’s first season in Dallas) through 2016-17 (the final year of Jamie Benn’s second-most-recent contract), the Stars allocated just $5.25 million in cap space to Benn and a mere $5.75M to Seguin. You could very fairly argue that Benn and Seguin were worth $11M apiece during that span, yet for four seasons, the Stars essentially deployed them at a buy-one, get-one-free rate.

Despite those incredible bargains, the Stars missed the playoffs twice and only won one playoff series during those four seasons. They squandered another bargain Seguin season in 2017-18, too, as they missed the postseason once again.

The Stars now enter 2018-19 with Seguin in a contract year, and GM Jim Nill told Mark Stepneski of the team website that the Stars hope to hammer out an extension, and that there’s “continued dialogue” on that subject.

From here, Nill touched on what should be some good advice for Seguin: he’s probably better off waiting to see if this team will finally put things together. Nill provided that comment when asked if an extension might happen before the season begins.

“I hope so. But I think I have mentioned from Day 1 that I don’t want people to panic if he is not signed when the season starts,” Nill said. “I think the biggest thing is we need to have a good season — get off to a good start. I hope he is signed by then, but I know if he isn’t, we’ll get a good year out of him and go from there. But like I said, I am hopeful we can get it done. We’ll have to see.”

Look, few would credibly question Seguin if he just decided to ink an extension this summer.

The threat of injuries makes an early extension very appealing, and the 26-year-old starring Star should make a bundle of money even if he leaves a healthy chunk on the table, which has to be a concern for a player who’s been sorely underpaid for his entire NHL career.

Seguin is presented with some undeniably relevant peripheral reasons to ink an extension beyond “wanting to swim in gold coins like Scrooge McDuck.” While the Stars have been disappointing during his stay relative to the ceiling many would picture, they have some fantastic supporting cast members, particularly Jamie Benn and John Klingberg. It’s almost certainly not lost on Seguin that Dallas features tax-related perks associated with “non-traditional hockey markets,” and also boasts a more easy-going media atmosphere than one he’d experience in, well, a “traditional hockey market.”

So don’t be surprised if he shrugs his shoulders and votes for the certainty and security that would come from a long-term contract.

It would be far more interesting if he waited things out, though, especially if Seguin values a chance at the Stanley Cup more than anything else. Let’s ponder some of the thoughts that might go through the splendidly talented forward’s head if he was assessing the Stars’ efforts and chances.

This isn’t exactly a “budget” situation – As great as Dallas has been at landing splashy trades and free agent signings, they’ve also made some big blunders. They’ve moved away from more modern-style defensemen (Alex Goligoski, Jason Demers), instead pursuing old-school types (Marc Methot, Roman Polak) who clash with the style that left opponents gasping for air during Dallas’ best moments. The struggles seem to continue regarding finding answers in net; Ben Bishop seems more stable than Antti Niemi and Kari Lehtonen, yet would the Stars be as excited to sign his risky deal in 2018 as they were merely in 2017?

So, yes, there’ve been some mistakes, but as much as the strikeouts sting, it’s better to swing for the fences than to walk away from possible solutions. It’d be far more dire if Seguin was pondering, say, the Senators’ outlook.

Seguin can confidently state that the Stars tried to leverage bargains like his deal, despite the lack of success. Some of those moves do work out, too, like the signing of Alex Radulov, so that would have to be a pretty big plus.

Testing out the new coach – Hey, it probably helps the Stars’ chances to move on from Ken Hitchcock. As wise as Hitch is, and even if he’s mellowed a bit with old age, he’d probably fall short of “players’ coach” status.

Jim Montgomery could end up being a taskmaster, too, yet there’s a strong chance he will – at minimum – lean toward a faster style, which would almost certainly appeal to a superbly talented player such as Seguin.

Some reasons to be optimistic – The Stars have a few players who might nudge them toward the sort of supporting cast that can finally give them sorely missing depth.

That’s true if Miro Heiskanen can make good on his potential as the third pick of the 2017 NHL Draft. Valeri Nichushkin‘s been a big disappointment, yet with the goal posts moved to a different position during his next Stars tour, he’d be a great find if he can merely fit in nicely on a prominent line. Some other young players may flourish under Montgomery, with Julius Honka standing out as a plausible beneficiary.

(There’s also the Erik Karlsson possibility, though those rumblings have died down for not just the Stars, but everyone else. Then again, the notion that the Stars are willing to spend money to make money might come back into focus there.)

Joyless division – I’d venture a guess that, as tuned-in as NHL players are these days, Tyler Seguin probably doesn’t factor the toughness of the Central Division much – or at all – into his future decision. Such a thought would likely be silly when considering a long-term contract, as things change fast in sports.

(Plus, Seguin might not be as plugged-in as others, considering that he at least claimed to have never heard of a “Gordie Howe hat trick.” C’mon, Tyler.)

That said, the ruggedness of the Central Division might hurt his viewpoint of Dallas’ chances as a contender if Seguin decided to really wait things out. The Stars could conceivably make big gains in 2018-19 and still fizzle out in the postseason simply because just about everyone’s likely to struggle against the Nashville Predators and Winnipeg Jets. It’s conceivable that the Stars leap yet still end up with the third seed, fall in the first round despite a good effort, and still seem disappointing.

If that happens and Seguin hasn’t signed an extension, well, who knows? We could see a John Tavares-type situation, even in an arguably superior situation than the one the Islanders offered.

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Ultimately, this could end up being a pretty simple situation for Seguin. Maybe he has a sweet spot in mind for term and/or AAV, or merely just some no-trade-type provisions. It would be silly to lampoon him for any of that, especially when he’s cashing checks, playing on what should be a competitive team, and not shivering during the winter.

On the other hand, the Stars haven’t enjoyed a ton of success since braining the Bruins in that Seguin trade, and the second pick of the 2010 NHL Draft might just want to explore the free agent market.

What would you do if you were in Seguin’s shoes?

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James O’Brien is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @cyclelikesedins.