Even the smug man in charge at NHL headquarters would surely agree last week was an especially bad one.
As he addressed the league's board of governors in New York, Gary Bettman admitted he had no clue that two of his closest NHL confidants - L.A.'s Philip Anschutz and Minnesota's Craig Leipold - had lent San Jose banker Boots Del Biaggio a combined $17 million (U.S.) to help him pay for a $25 million stake in the Nashville Predators.
NHL owners were speechless, according to a source who attended the meeting, as Bettman grumbled he had been in the dark. Neither Anschutz nor Leipold had made him aware of the cozy back-door deal.
Del Biaggio, of course, has become the NHL's most famous owner. He's the target of a criminal investigation, faces at least a half dozen lawsuits, and has been filed with divorce papers for allegedly lying about his financial wherewithal.
Although Leipold's motivations are murky, Anschutz likely lent Del Biaggio the money because his company owns an arena in Kansas City and Del Biaggio wanted to move the Predators there.
"Anschutz and Leipold are on Gary's executive committee," says one high-ranking NHL source. "These are guys who are at the power centre of the league, close to Gary, and supposed to be his best allies. And here they were lending Del Biaggio money, and not telling Gary, at a time when they were supposed to be reviewing his offer to become an owner.
And now, with some of his owners viewing the NHL's front office as nothing short of a banana republic, Bettman's month gets worse.
Ducks owner Henry Samueli is a long-time California philanthropist turned perjurer and felon. Yesterday, he beat Del Baggio to the punch by pleading guilty to lying to federal authorities.
The model of the modern-day NHL owner who bought the Ducks in 2005, Samueli faces five years probation and $12.2 million (all figures U.S.) in fines after admitting he lied last year when U.S. Securities and Exchange Commission officials asked him about a stock options scandal at his company Broadcom.
Will the NHL force Samueli to sell the club? It's uncertain. The league offered no comment yesterday. But then what could it say?
After all, here's what deputy commissioner Bill Daly offered last month when the SEC first charged Samueli with scheming to defraud Broadcom shareholders: "Today's announcement has no impact on Henry's status as an NHL owner or on his ownership of the Ducks. Civil litigation happens all the time. That doesn't disqualify anybody from owning a franchise, much less an NHL franchise."
Bettman added: "The Samuelis have been terrific owners. They're perhaps the most community-minded and charitable people in all of Orange County," Bettman said. "I am not going to fret about something that may or may not be substantiated at the end of the day."
Right. No sense fretting. Maybe Bettman and Daly couldn't have predicted yesterday's news but certainly "this matter's before the courts, so we decline comment" would have been a shrewder move.
Trouble is, Bettman and Daly think they're the smartest guys in any room. It won't be a shock if the league sticks by Samueli instead of making what amounts to a no-brainer. There should be no room in the ranks of NHL ownership for felons and perjurers - even if they are philanthropists.