The Detroit Red Wings are in the midst of one of their most intriguing summers in recent memory. Typically considered one of the most steady teams in professional sports due to their tremendous playoff streak — you might have heard of it? — Detroit’s fan base has been rattled by a sequence of postseason failures.

2008 seems like a long time ago, and the Red Wings have made it out of the first round just once in the last five years. Their core players are aging, there a few just-bad-enough-to-matter contracts on the roster and Ken Holland has been reluctant to make drastic changes.

The time has come for this organization to evolve or die. Holland has stuck to his way of doing business since July of 1997, but if Detroit wants to remain relevant he needs to start approaching the cap era differently. There isn’t a better way to stress this point than the way J.J. From Kansas did recently for WingingItInMotown.com:

The Red Wings are a team dangling from a precipice with nothing but their vast and jealousy-inducing history in hockey’s modern era to hang on to. The only thing separating the Wings from being a loser team like Vancouver, or Buffalo is having won Stanley Cups. What separates them from also-ran chumps like Colorado is never having to have dropped out of the playoffs on their run.

How can Detroit pull itself from the icy depths below while still winning hockey games? It all begins with the draft, where the Red Wings can’t afford to strike out with their first-round selection. Last year we saw that the right young player can make an impact in Dylan Larkin, and Holland may be looking for that same kind of option once again in 2016.

Let’s take a look at some scenarios that could present themselves in the days leading up to the draft in late June.

What will Pavel Datsyuk do?

The Pavel Datsyuk situation has been covered ad nauseam for a reason. He could badly handicap the Red Wings should he decide to leave the NHL and he knows it. It’s a reality that Holland should have been preparing to face as soon as the news broke earlier this year, and it sounds like the GM should be preparing for the worst.

Detroit is on the hook for Datsyuk’s $7.5 million cap hit even if he bolts for Russia. For a team that is in cap hell already, that is a monster blow. The player has said that he wishes he had taken one-year deals, but doing that would have inflated his AAV. We all know how much Holland loves to drive down cap numbers by tacking on extra years to contract.

It’s a move that pays off if Datsyuk plays, but it seems likely that he will be moving on from the NHL. That’s not something anyone should blame him for, and Holland has stated that the veteran will let Detroit know where he stands in June. Or just in time for the draft. If the 37-year-old is leaving, then it’s up to the Red Wings to find some way to ditch at least part of his cap hit.

That would come in the form of moving the contract to a team looking to get to the cap floor. That could be tricky though, since the rival GM won’t be able to just stash Datsyuk on the LTIR like what the Arizona Coyotes are doing with Chris Pronger or the Toronto Maple Leafs are doing with Nathan Horton.

Any organization taking on Datsyuk would essentially be doing Holland a favor, and there’s no such thing as a free lunch. We’ve discussed how the Red Wings shouldn’t handle this move elsewhere, but this will be one of the can’t-miss storylines heading into the draft. What Detroit can and can’t do as far as trades and free agency go will almost totally be decided by Datsyuk and how Holland solves this problem.

If a trade for this contract is going to happen, we could see it occur at the draft. And then the kind folks in Detroit will finally have a reason to throw another parade.

Can the Red Wings shed Jonathan Ericsson?

The Red Wings don’t have any glaringly awful contracts on the books, but they do have several lackluster deals eating up precious cap space. If you’re looking for a poster boy for players who are simply making more than they are worth, look no further than Jonathan Ericsson. The 32-year-old defenseman carries a cap hit of $4.25 million but is typically a drag in all three zones.

Detroit tries to shoehorn him into top-four roles, but he’s just not capable of playing the 18 minutes a night at this stage of his career. He’s slow, consistently makes mistakes in the defensive zone and isn’t particularly good at the stretch pass–something that head coach Jeff Blashill found out the hard way last October.

What are Jonathan Ericsson's odds of being a better defensman next season? Can't be worse than 5,000-to-1. — Tom Mitsos (@tom_mitsos) May 2, 2016

Would someone (anyone?) be interested in taking this player on for another four years?

This would be another do me a solid sort of trade for Holland, and he would likely need to give up a promising prospect or draft pick to get a deal to go through. And then the Red Wings could be down two of last year’s top-six defenders, since Kyle “totally worth a first-round pick that turned into Andrei Vasilevskiy” Quincey might not be back with the club in 2016-17.

If the Red Wings can’t find a taker for Datsyuk’s millions, they may be forced to examine other routes to cap relief. Flipping Ericsson and a prospect to a team looking for a touch of help on the blue line could be an option.

Is now the time to trade Jimmy Howard?

Datsyuk has nothing to offer another team outside of help to the cap floor, while Ericsson’s trade value is pretty limited. Jimmy Howard isn’t in that same boat for the Red Wings, and he is the team’s best trade chip heading into the draft. With teams like the Calgary Flames, Toronto Maple Leafs and Carolina Hurricanes looking for goaltending help, there’s a small market for the on-again-off-again starter.

Petr Mrazek will likely start 2016-17 as Detroit’s No. 1 goalie, which makes Howard a bit of an expensive backup. We could see Blashill try to run the goalie carousel for a second consecutive year, but having upwards of $10 million tied up in two goalies isn’t great cap management. Especially since the Red Wings are in tough shape as it is.

Mrazek is an RFA this summer and is line for a sizable raise over the $737,500 he made last year. Howard has three years left on a contract that pays him $5,291,666 on average and could be an attractive option since there aren’t many solid options available in free agency. James Reimer is arguably the best name that could be out there, so the draft may be the perfect time to move Howard.

Detroit needs help on the blue line and could use some scoring pop too. Holland needs a little bit of everything at this juncture, so if there’s a fair trade on the table at the draft he should jump at the chance to clear Howard off the books.

Who will Detroit target in the first round?

The Red Wings nailed their selection of Larkin last year and will look to acquire another player of that ilk with their No. 16 pick this summer. Their system is a bit thin down the middle, and with Henrik Zetterberg turning 36 this year, Holland could look at drafting a center. It’s highly unlikely that the team will look to add depth on the wing as they are already flush with young talent there.

Larkin played wing as a rookie but he was drafted as and listed as a center. He could eventually shift back to that spot, meaning that the Red Wings will eventually need a No. 2 pivot behind him.

No one can deny that the team badly needs reinforcements on the blue line though, and Holland could dip into this draft’s glut of mid-round defensemen to shore up this need. Here are a few options he may consider once taking the stage in Buffalo.

— Michael McLeod (C) – This would represent a bit of a fall for the highly touted center, but not to the point of being unrealistic. Our own Robert Nasso characterized McLeod as a “diamond in the rough” recently, and that’s precisely the kind of player Holland should be looking for.

— Tyson Jost (C) – Likely the hottest 2016 draft prospect right now, Travis Jost caught the hockey world off guard when he broke Connor McDavid’s World U18 tournament scoring record in April. Despite that, coming from the BCHL may hurt his stock a bit as he hasn’t played against the best competition possible. Another high-end player who could slip to Detroit at 16.

— Dante Fabbro (D) – There will be some interesting names on the board when the Red Wings make their pick, but defenseman Dante Fabbro’s could be exactly what Detroit needs on the blue line. He’s not an electric offensive talent, but he’s noted for making smart plays without hesitation and has drawn comparisons to Brent Seabrook.

— Charles McAvoy (D) – A smooth skater who knows how to skate the puck out of trouble, Charles McAvoy could be the kind of offensive catalyst Blashill needs to run the system he originally wanted to implement in Detroit. The Red Wings could use some speed on the back end, and the Boston University standout has it in spades.

— Adam Fox (D) — If Holland is in the mood to shoot for the moon on draft day, Adam Fox could be his selection. The 5-foot-10 defender needs work in his own zone but is a wizard on the power play and in the offensive zone. Detroit hasn’t been great with the extra man over the last few years, and Fox could be the sort of player capable of fixing that down the road.