As per David Staples last week in the Edmonton Journal, two pieces of history popped up - that Glen Sather offered Don Cherry a scouting job with the Oilers were he ever fired from CBC, which for him was a common threat since he tended to say controversial things on the air. That never materialized as Cherry of course would go on to be a hockey commentator for many decades. Cherry eventually did get fired but not until 2019, and by then he was in his late 80s and too old to be a scout for any team - not to mention with a net worth of $14 million Cherry has the money to do what he wants at his age.
The other tidbit is that Mark Messier requested a trade out of Edmonton after their 1990 Cup win. To those of us who have read his autobiography, this is not news because it was revealed in this book, but it came as a shock to those who hadn't heard it before. There were many reasons all coming together at once to make Messier request a trade.
He was a little sore at owner Peter Pocklington for initiating the Gretzky trade a year earlier and could see that Pocklington's financial empire was crumbling around him, and it later came out that Pocklington was running a bare bones operation for the Oilers towards the end as they would use much of his Oilers revenue to prop up the rest of his businesses (Pocklington's businesses were failing due to a combination of interest rates, shady business practices, and a bad reputation following him around Edmonton, and the details of the Gretzky trade certainly didn't help either).
After having won five Stanley Cups with the Edmonton Oilers, there were hockey reasons for Messier wanting out too - the desire for a new challenge, peaking in his achievements here in Edmonton (he'd won four cups and captained the team to another - the last one proving the Oilers could win without Gretzky), and believing the Oilers needed a retool at the least as the core was all getting older. He'd also had to say goodbye to valued teammates and friends in not only Gretzky, but Paul Coffey, Grant Fuhr, Glenn Anderson, and Jari Kurri over the years and likely wanted that to stop.
He was asked where he wanted to go and the New York Rangers were at the top of his list, not just because at the time they were more financially stable but also because he wanted to help them lift the 54 year old curse that New Yorkers believed was preventing them from winning another Cup. That trade of course did come to fruition and the rest is history.