A Ryan O'Reilly trade is more complicated than we think Reports have surfaced over the last two weeks that the Colorado Avalanche are shopping centre Ryan O'Reilly and that the Buffalo Sabres and Toronto Maple Leafs are potential trade partners. But as TSN Hockey Insider Bob McKenzie writes, putting together any deal for O'Reilly is not that easy.

Bob McKenzie TSN Hockey Insider Follow|Archive

In a previous life, when I spent more time in an arena writing about hockey than in a TV studio talking about it, I would drive home from games at Maple Leaf Gardens listening to the post-game radio call-in shows. Disgruntled Leaf fans – are there any other kind? – would phone in their trade suggestions.

Hilarity would often ensue.

Joe from Woodbridge – not to be confused with the Joe from Woodbridge who now works behind the scenes on That's Hockey (although, now that I think about it...) - would inevitably come up with something along the lines of: "I think the Leafs should trade Bill Berg for Joe Sakic."

Uh...okay, then. Still, it was damn fine fun.

And now, with the NHL trade deadline just six weeks from today, I want in on some of that action.

"Hi, I'm Bob, long-time listener, first-time caller...I think Colorado should trade Ryan O'Reilly to Buffalo for Tyler Myers.

One for one. Boom. Done. I'll hang up and listen."

If only it were that easy.

***

Where to begin?

If the Colorado Avalanche and soon to be 24-year-old centre Ryan O'Reilly were on Facebook, their relationship status would be tagged as "complicated."

Not surprisingly, that would also characterize the ongoing trade talks involving O'Reilly.

Former Denver Post hockey writer Adrian Dater, on Dec. 28, was the first this season to tweet Colorado was offering O'Reilly around the league in exchange for a quality defenceman. In the wake of that, some NHL clubs with interest in O'Reilly said they hadn't been contacted by the Avalanche, so O'Reilly certainly wasn't being auctioned or shopped league-wide.

What has apparently happened, though, is the Avalanche have quietly targeted a few specific teams – Buffalo and Toronto are the ones mentioned most often in rumours, but absolute confirmations have been hard to come by and it's been suggested to me Toronto and Colorado have previously had conversation about O'Reilly but nothing recently – they see as the best fit in terms of having both significant interest in O'Reilly and also the requisite blueline piece or pieces that Colorado wants and needs in return.

For the right price, it's believed that Avalanche executive vice president and general manager Joe Sakic and head coach Patrick Roy are prepared to trade O'Reilly before the Mar. 2 deadline. But that isn't to say O'Reilly is certain to be dealt before then.

Maybe it will happen in the summer. Maybe it doesn't happen at all. That, too, gets awfully complicated.

Before we can go all Joe from Woodbridge about the prospect of O'Reilly becoming a Sabre or a Leaf, or Tyler Myers or Jake Gardiner becoming a member of the Avs, we really are obliged to look at the history of the relationship between O'Reilly and the Avs because that - and how it plays out in the weeks and months to come - impacts every aspect of a potential trade.

***

The first and most important thing you must know about O'Reilly is his contract status. When this 2014-15 season ends, O'Reilly has one year left on a deal that will pay him $6.2 million next season with a cap hit of $6 million. When that 2015 -16 season is over - as long as he doesn't sign a contract extension before then - O'Reilly will become an unrestricted free agent a year this July. And at the ripe, old age of 25.

And that's a really big deal. Any team looking to trade for O'Reilly now and giving up significant asset(s) in the process, has to be wary of the player's impending UFA status in 2016. Imagine, for example, if Buffalo surrendered their 6-foot-8 defenceman (Tyler) Myers for O'Reilly, only to have the latter skate into UFA status a season and a half from now.

It's not necessarily an insurmountable issue. It may be in Colorado's best interests to give a team trading for O'Reilly permission to talk to the player's representation to see if they can work out a long-term contract extension. That's how Colorado can get maximum yield on an O'Reilly trade, but it can also give the player undue influence on the trade process. So whether permission and/or a contract extension happens or not, well, that's a significant and as yet unknown variable.

Equally as interesting as O'Reilly's contract status is the long, winding and often bumpy road he and the Avalanche have travelled together for the past three seasons in particular.

On that note, it's difficult to talk about O'Reilly and his contract(s) without mentioning teammate Matt Duchene and his contract(s). It would seem the two have been inexorably linked from the get go, on and off the ice.

Duchene was chosen third overall by Colorado in the 2009 NHL draft. O'Reilly was taken 30 slots later, 33rd overall, in the second round.

To no one's surprise, Duchene used his electrifying speed and skill to make the Avs as an 18-year-old (24 goals and 55 points in 81 games). To the surprise of many, O'Reilly, whose game is as complete, responsible and detail-oriented as Duchene's is exciting and productive, also made the team as an 18-year-old (eight goals and 26 points in 81 games).

Both Duchene and O'Reilly showed improvement in their second seasons. Duchene jumped up to 27 goals and 67 points in 80 games. O'Reilly posted 13 goals and 26 points in 74 games.

In their third and final year of their respective entry-level deals, Duchene took a major step backwards with only 14 goals and 28 points in 58 games - while O'Reilly made a big leap forward to 18 goals and 55 points in 81 games.

If Duchene had designs on the big buck ($5 million to $6 million AAV), long-term (five or six years) second NHL contract that have become something of the norm for franchise building-blocks, his weak platform-year performance gave Colorado the leverage to offer a two-year bridge deal with an AAV of $3.5 million, which Duchene readily accepted the summer before the NHL lockout of 2012-13.

That, however, is where Duchene and O'Reilly hit the fork in the contract road. Sort of.

Colorado, initially anyway, wasn't offering O'Reilly the two-year, $3.5 million per year deal Duchene got and by the time the Avs did make that offer to him, O'Reilly wasn't prepared to take it - not after his platform season was so much better than Duchene's. The Avs argued Duchene's three-year body of work was more prolific than O'Reilly's, but the latter was sticking to his guns and even after the lockout-shortened season began, O'Reilly stayed in Russia playing for coach Paul Maurice in Magnitogorsk alongside Ryan's older brother Cal.

That's when the Calgary Flames swooped in with a two-year offer sheet to O'Reilly in late February, which Colorado matched to keep him in the fold. But at a price.

The offer sheet gave O'Reilly $3.5 million in the first year, but jumped all the way to $6.5 million in the second year. Most noteworthy, though, was that $2.5 million of his $3.5 million income in the lockout year was a signing bonus, paid in full regardless of the fact O'Reilly played only 29 games in the 48-game lockout season.

The next season, Duchene continued to make $3.5 million while O'Reilly's salary jumped to $6.5 million. Duchene, though, received a five-year, $6 million per year contract extension the year before his bridge deal expired. When O'Reilly's bridge deal expired last summer, the Avalanche took a hard line with O'Reilly, taking him to seldom-used, club-elected salary arbitration.

It was widely perceived as a potentially hostile maneuver by the team. But immediately before the arbitration hearing, the Avs and O'Reilly agreed to his current two-year deal at $5.8 million and $6.2 million with an AAV of $6 million, the same AAV as Duchene's five-year extension. The difference is Colorado bought up the first three years of Duchene's unrestricted free agency (until the summer of 2019) for $6 million per year, while O'Reilly is on the verge of hitting his maximum earning power in the summer of 2016 without having sacrificed any prior income.

In fact, because of the offer sheet structure, O'Reilly actually made millions more than Duchene in three years since they came out of entry-level.

"You know what all of that tells me?" an NHL management-type told me yesterday. "One, (O'Reilly) will expect and is quite likely to get between $6.5 million and $7.5 million, if not more, per year on a long-term deal.

"Two, if you're trading for him now and giving up what Colorado expects to get, you better know you have (O'Reilly) signed to that extension."

***

Technically, the Avs don't absolutely have to trade O'Reilly. They have the cap room to keep him but they're not going to like the cost of potentially paying him more than Duchene, and they do have an internal budget they adhere to. That's why Paul Stastny was allowed to walk to free agency (and St. Louis) last summer and why most feel it's inevitable they won't allow O'Reilly to do the same thing without getting something in return.

So conventional wisdom is even if O'Reilly isn't traded by this year's deadline, he'll almost certainly be moved in the summer. Even if O'Reilly did a long-term extension with Colorado in the summer, he'd be leaving himself exposed to be traded next season. A full no-trade clause wouldn't kick in for another year, so signing an extension with the Avs would leave the player exposed and possibly traded next season with no say on his destination.

That's just not going to happen. The only way O'Reilly stays in Colorado for the long-term is if he signs his extension there once his existing deal expires in 2016.

Besides, with Duchene as the established No. 1 centre and Nathan MacKinnon clearly emerging as the No. 2 (MacKinnon's entry-level contract expires the same summer as O'Reilly goes to UFA), O'Reilly may simply be a luxury Colorado can no longer afford, especially when there is such a glaring need on defence.

If so, it's still going to be a painful decision.

O'Reilly's numbers this season – eight goals and 25 points in 46 games – are way off his career year in 2013-14. The Avs have taken a considerable step backwards as a team, too. But O'Reilly continues to be perceived as one of the more complete players in the NHL, whose versatility (wing or centre), specialties (faceoffs, penalty killing, shutdown duties) are way above average, as are the so-called intangibles (character, leadership) that, with more than a modicum of offensive potential, make him Jonathan Toews Light. Or something like that.

O'Reilly appears to like playing for head coach Patrick Roy and the feeling seems to be mutual, but both the Avs and O'Reilly have repeatedly demonstrated to each other over the last few years that they aren't shy about using whatever business/CBA tools are at their respective disposals.

All of which suggests O'Reilly is likely to be dealt, whether it's before Mar. 2 or in the off-season.

***

It isn't often there's an NHL trade fit that seems so patently obvious as to be almost perfect for both teams involved, but Ryan O'Reilly for Tyler Myers may be as close as you can get.

Colorado is believed to be looking for a right-shot defencemen to bolster a right side that already features Erik Johnson and Tyson Barrie. A mobile, 6-foot-8 shutdown blueliner with some offensive upside like Myers would fill a considerable void on the Avs' blueline. Having young building block forwards such as Duchene, MacKinnon and Gabriel Landeskog would help to mitigate the loss of O'Reilly.

Myers, who turns 25 next month, is a year older than O'Reilly but is still not yet even really in his prime. He's had a lot of ups and downs since winning the Calder Trophy as rookie of the year in 2010, but he's certainly demonstrated this season that he's still capable of playing the game at a high level. He's also a fixed-cost asset, under contract for four more years after this one with a $5.5 million cap hit, but an actual cash outlay of only $15.5 million over those four years. That would be an extremely dollar-friendly deal for Colorado.

As for the Sabres, O'Reilly would be a tremendous stabilizing influence on a very young team in the middle of a massive rebuild. If the rest of the season and the draft lottery go according to plan, there's an excellent chance Buffalo will end up with centre Connor McDavid or centre Jack Eichel. Either one would represent a potential No. 1 offensive centre. O'Reilly, with his versatility, complete game and leadership, would be a wonderful mentor in the No. 2 slot, with last year's second overall pick Sam Reinhart as a great potential No. 3 centre.

Buffalo would miss Myers' presence on the blueline, but with big youngsters Rasmus Ristolainen and Nikita Zadorov already playing in the NHL, the Sabres would have some big, mobile blueliners with significant upside to still build around.

The Sabres certainly have the cap space and Buffalo owner Terry Pegula has the deep pockets to meet or exceed O'Reilly's anticipated contract demands. The reality is the Sabres could justify the premium required to keep O'Reilly in the fold because they know a small-market, rebuilding team would have to overpay to take a talent like O'Reilly out of free agency.

Are there risks involved? Absolutely.

Perhaps Myers never fully rounds back into top-pairing form. Maybe O'Reilly never matches his offensive output of last season. But each has enough attributes to suggest neither would be a bust and whatever risk is involved, it's equally shared by both teams.

I was curious to get a sense from some NHL GMs and assistant GMs if they viewed O'Reilly for Myers even up as an equitable transaction. The majority I talked to thought it was a fine fit, a one-for-one that works from both sides and requires no additional picks or prospects.

One management-type who puts higher value on O'Reilly than Myers thought the Sabres should also send a draft pick to Colorado. But another said the financial discrepancy - Myers' cost efficiency versus the more costly anticipated UFA premium for O'Reilly – means Colorado should throw Buffalo a little something extra.

So there you have it - my Joe from Woodbridge moment.

***

There are a lot of moving parts on this Ryan O'Reilly scenario and it could still go in a number of directions. All I think I know is he's unquestionably in the driver's seat.

By all accounts, he's happy in Colorado. If the Avs don't trade him, it will be no punishment for him to remain exactly where he is, because he knows he's less than 1 1/2 seasons from calling his shot on where he wants to possibly finish his NHL career.

If the Avs see fit to move him before the deadline or in the summer, he may have to decide a little sooner than 2016 if he's prepared to commit long-term to a new home somewhere else. Or he can just wait everyone out, play whatever cards are dealt in the short term in Colorado or elsewhere this season or next and ultimately do whatever suits his fancy beyond that.

Either way, you have to figure the man is going to get paid and he'll be playing long-term wherever he wants to be.