Hiring a new CEO of Hockey Operations usually wouldn't generate a ton of concern from hockey fans. On average, an announcement like this one would drift by pretty quickly in the hockey community. However, today when the Oilers hired Jeff Jackson there were some legitimate concerns brought up by respected journalists and fans who believed there may be some hypocrisy at play.
The Wasserman Hockey Agency was founded in 2018 and before joining the Oilers, Jeff Jackson was their executive vice president. During his time with the agency he also represented players like Alex Debrincat, Aaron Ekblad, Quinton Byfield and more importantly Connor McDavid. Earlier today Connor announced that he will be staying with Wasserman but will now be represented by a different agent. Surprisingly this isn't the only concerning Connor connection. Jeff also represented Connor Brown, who signed on July 1st to a one year, bonus-heavy contract in Edmonton.
Back in May the NHLPA said they were going to investigate Kyle Dubas after they learned he is a client of the Wasserman agency. This normally wouldn't be cause for investigation but in this case it was because the Wasserman agency also represents Auston Matthews. There were concerns there may be a conflict of interest there. As of now the NHLPA has said nothing about the hiring of Jeff Jackson. It's hard to say whether or not there's something shady going on but there should probably at least be a review.