Just one day after trying (and failing) to land Avalanche free agent Ryan O’Reilly with an aggressive offer sheet, Jay Feaster and the Calgary Flames found themselves in the center of a controversy over whether they’d almost committed an all-time blunder.

According to a report, the Flames would have had to place O’Reilly on waivers as soon as they signed him. That means Calgary would have given up the draft pick compensation and the $2.5 million signing bonus, only to see its new player immediately wind up elsewhere. That didn’t end up happening, because the Avalanche matched the offer sheet, robbing us all of what would have no doubt been a fascinating legal scramble, but the incident embarrassed the Flames and has fans calling for Feaster’s head.

All of which puts Feaster & Friends in good company. After all, NHL hockey is complicated business, and the Flames’ offer-sheet saga certainly wasn’t the first time that somebody in the hockey world found themselves getting tripped up by a legal loophole.

Whether it was through confusion, dishonesty, or just plain old incompetence, here are some infamous moments in NHL history that had fans and team officials alike scratching their heads and checking their rulebooks.

Pat Quinn’s ‘intolerable position’

Christmas appeared to have come early for Pat Quinn on December 24, 1986. That was the date he signed a contract to become the new president and general manager of the Vancouver Canucks, effective on June 1 of the following year.

There was just one minor problem: Quinn already had a job at the time. He was coach of the Los Angeles Kings — one of Vancouver’s division rivals.

Quinn claimed that he had found a loophole in his contract: The Kings had missed a deadline on some paperwork, making him eligible to negotiate with other teams. The league attempted to dispute that, before realizing that they somehow didn’t have a copy of Quinn’s contract on file anywhere. To put an exclamation point on the entire debacle, it took the Kings two weeks to inform the league what had happened.

In the end, NHL president John Ziegler ruled that the signing represented a clear conflict of interest. He slapped Quinn with a multiyear ban from coaching and handed out six-figure fines to both teams.

Whether you agreed with Ziegler’s decision or not, you had to at least give him credit for showing up. Unlike our next moment …

The case of the missing president

The “have another doughnut” incident is one of the most memorable in league history (we had some fun with it a few weeks back), and most fans know the main details: the alleged ref bump, the “you fat pig” insult, the suspension of Devils coach Jim Schoenfeld, the restraining order, the wildcat referee strike, and finally the replacement officials in yellow jackets who couldn’t skate.

But the story actually includes a mystery subplot that’s been largely forgotten: Why did the Devils go to court for a restraining order in the first place? Why didn’t they just appeal their coach’s suspension to league president John Ziegler?

As it turns out, they had a good excuse. During an embarrassing crisis occurring in the middle of the conference finals, Ziegler couldn’t be located. He just went missing. For days.

How do you appeal to a president who’s gone AWOL? You can’t, the Devils figured, so they went to court.

Blackhawks owner Bill Wirtz claimed Ziegler had left him in charge, and insisted he had everything under control. But rumors flew about the missing president’s whereabouts. One especially bizarre report indicated that he was helping his son escape a cult.

It wasn’t until days after the doughnut incident that Ziegler finally made his presence known — via conference call, from an undisclosed location. To this day, nobody seems to know exactly where he was.

Mike Keenan bolts Broadway

You might assume that a coach who led a New York team to its first championship in 54 years would be the toast of the town. But then, Mike Keenan was never like other coaches.

Less than a month after the Rangers won the Cup, Keenan blindsided the team by announcing they’d been one day late on a bonus payment. The coach declared himself a free agent, and oh by the way — he’d just signed a five-year deal with the Blues.

The Rangers, needless to say, did not agree with Keenan’s interpretation. While acknowledging they were late on the payment — GM Neil Smith called it a “clerical error” — New York argued that it wasn’t a material breach that should void Keenan’s contract. The Rangers filed a lawsuit against Keenan and demanded commissioner Gary Bettman deliver a ruling.

Bettman eventually allowed Keenan to go to St. Louis, but suspended him for 60 days and forced the Blues to give up Petr Nedved as part of a compensation package. He also fined the Blues, Rangers, and even the Red Wings (who, as it turned out, had also tried to negotiate a deal with Keenan).

The jammed fax machine

The Bruins took power forward Kyle Wanvig with their third-round pick in the 1999 draft, but hadn’t been able to reach an agreement with him leading up to the two-year deadline to sign drafted prospects. With Wanvig about to go back into the 2001 draft, the Bruins made a last-minute trade with the Maple Leafs for Jonas Hoglund and a draft pick. The Leafs quickly agreed to a contract with Wanvig, and the Bruins posted news of the deal on their website.

Then the Maple Leafs’ fax machine jammed.

That technical delay — just a few minutes long — was enough to cause the Leafs to miss the NHL’s deadline to have all the paperwork filed. The league scrapped the deal, Wanvig went back in the draft, and Hoglund stayed in Toronto.

In the end, everyone lost. The Bruins lost a prospect for nothing, Wanvig never did pan out as an NHL player, and Hoglund spent two more years being criticized in Toronto as the poster child for the “lousy Mats Sundin winger” club.

‘Ottawa apologizes’

The Ottawa Senators came to life on June 18, 1992. They did not get off to a good start.

Midway through the expansion draft, the Senators announced that they’d selected Montreal tough guy Todd Ewen. But Ewen was no longer eligible, because the Canadiens already had lost two players. The league pointed out the error, causing Senators GM Mel Bridgman to infamously respond, “Ottawa apologizes.”

It would get worse. A few minutes later, Bridgman announced the Senators picked Todd Hawkins of the Maple Leafs. But the Leafs also already had lost two players, so Hawkins wasn’t eligible anymore, either. Next, Bridgman tried his luck with C.J. Young. The league informed him that Young hadn’t even been on the eligible players list in the first place.

How did the Senators get it so wrong? According to one version of the story, Ottawa had all its scouting reports stored on a single laptop but forgot to bring a backup battery. Once the computer died, so did Ottawa’s list. Not to mention its credibility.

Gil Stein, hockey Hall of Famer

Gil Stein’s reign as the most powerful man in the NHL could be described, if we’re being kind, as short. If we’re not being kind, we could describe it as a disaster.

Stein took over from Ziegler as NHL president during the 1992 offseason. By the following February, the league had named Bettman commissioner, essentially making Stein’s role irrelevant. During his few months on the job, Stein is perhaps best remembered for his creative approach to discipline, in which suspended players didn’t necessarily have to miss games. It’s fair to say hockey fans didn’t shed any tears over his absence.

But Stein had one last trick up his sleeve. Using the powers of the presidency that he still technically held, he rigged that year’s Hall of Fame voting to get himself elected.

When the vote was announced, fans went ballistic. Bettman demanded an investigation, which revealed that Stein had abused the process but hadn’t technically violated any league rules.

This story has a happy ending: Under pressure from fans, media, and Bettman himself, Stein eventually declined his induction.

A tale of two Stefan Nilssons

In the 12th round of the 1988 NHL entry draft, the Vancouver Canucks drafted 20-year-old Swedish forward Stefan Nilsson. This came as a surprise to the Calgary Flames because earlier that day — in the seventh round of the 1988 NHL entry draft — they also had drafted 20-year-old Swedish forward Stefan Nilsson.

When the Flames demanded an explanation from the league, they were informed that there were actually two 20-year-old Swedish forward Stefan Nilssons in that year’s draft. The Flames, according to the possibly apocryphal story that has made the rounds ever since, had accidentally picked the wrong one. They wanted this guy.

(In an alternate version of this story that crops up on hockey forums from time to time, the Nilsson drafted by the Flames actually turns out to be dead. Given that he was still posting stats in various leagues years later, that seems to be an urban legend.)

In the end, the confusion didn’t matter much, because neither player made it to the NHL. But it did have a curious epilogue: A full 12 years later, in the late rounds of the 2000 NHL expansion draft, the Minnesota Wild selected … 32-year-old Swedish forward Stefan Nilsson.

(It was the Canucks one. We think.)

Taro Tsujimoto

One thing you can say about Taro Tsujimoto: He’s no Stefan Nilsson.

No, the Buffalo Sabres’ 11th-round pick from the 1974 entry draft has never been accused of being two people at once. That’s because he was zero people. He didn’t exist.

That minor detail didn’t stop notoriously crusty Sabres GM Punch Imlach from drafting him with the 183rd overall pick. But this was no Bridgman-level screw up. Imlach simply got bored with a draft that seemed like it might never end (the rules allowed the picks to continue until all teams had passed), and he decided to have a little fun.

Imlach announced the pick, and it was dutifully recorded in the official record book. Tsujimoto also appeared in the league’s various media guides that year. Reporters from around the league, intrigued with the idea of a Japanese import having a chance at a roster spot, were reassured by Imlach that Tsujimoto would be arriving soon.

Imlach let the joke carry on for months before finally revealing the deception before training camp. The pick has since been stricken from the official record, but the legend of Taro Tsujimoto lives on. He even has his own hockey card.

The check is in the mail

In the summer of 2009, Dale Tallon had been the GM of the Chicago Blackhawks for four years, had rebuilt the team into a contender, and had just landed that year’s marquee free agent, Marian Hossa. Life was good.

Then he forgot to make sure his restricted free agents got their qualifying offers. A few weeks later, he wasn’t the GM of the Chicago Blackhawks any more.

Tallon did tender offers to each of the players involved. But the NHLPA argued that they hadn’t been received in time. In one version of the story, Tallon sent the offers out by mail but failed to get them to the post office for the July 1 deadline. If the players didn’t receive the offers in time, they would become unrestricted free agents — a disastrous blow to a Blackhawk team on the verge of contending.

It wasn’t an unprecedented mistake — the Devils once forgot to qualify future All-Star Brian Rafalski — and the Predators faced a similar issue with several players in 2011. But it was a costly one for Chicago. Each player eventually re-signed, but the team paid out far more money than they’d normally have had to.

Within days, Tallon was demoted to an adviser’s role. The Blackhawks team that he assembled went on to win the Stanley Cup the next year.

The Lindros trade(s)

Eric Lindros entered the 1991 draft as the most hyped prospect since Mario Lemieux. But the Nordiques held the first overall pick, and Lindros had been clear that he wouldn’t play for the franchise. They picked him anyway, and he kept his word, going back to the OHL for another year while waiting for a trade that the Nordiques vowed would never come.

By the 1992 offseason, it was clear Lindros was going to get his way. The Nordiques were listening to offers, and by late June, it seemed inevitable that a trade was coming.

That turned out to be only half-right: Nordiques president Marcel Aubut actually traded Lindros twice on the same day. First, Aubut made a verbal agreement with the Flyers. Then, after getting what he felt was a better offer from the Rangers, Aubut agreed to that deal, too. As you can imagine, this created a bit of a problem.

Eventually the whole mess was handed over to arbitrator Larry Bertuzzi. (If the name sounds familiar, it’s because years later, his grandnephew would create some hockey-related legal trouble of his own.) After a week of hearings, Bertuzzi made his decision: Lindros would go to Philadelphia.

In hindsight, the Flyers might not have “won” the case. The Rangers kept the core of their team intact and won the Cup in 1994. The Nordiques got the best player in the trade, Peter Forsberg, and won two Cups in Colorado. And despite initially living up to the hype, Lindros ended up being an injury-plagued disappointment in Philadelphia.

His time with the Flyers ended in 2001 when he was traded to — who else — the New York Rangers.