Listening to The Vertical Podcast with Woj, he had a fantastic interview with Jerry Krause (former Bulls GM) he told a story about how afraid he was of trading with Red Auerbach, this seems the contemporary situation Ainge has.
Jerry Krause,
"My first year, morning of the draft, I get a call from Red...and Red wants to make a deal with me. He'll give me a second round pick, he'll give us, at that time Sam Vincent, who was a rookie with him...for a second round pick, he had a guy he wanted to take. And I'm thinking, boy I like Sam Vincent...somethings wrong, my antenna went straight up, wait a minute now. We had four to five hours before the draft started, I started making calls, I called Michigan State about Sam, I called his agent about Sam, I called anyone I could get a hold of about Sam Vincent. I could not get a negative thing about him, great kid, great young player...and I was still scared of Auerbach...and I backed out of the deal, Red called about four or five times but I said I was keeping the second round pick because I was scared of Auerbach...Auerbach had beaten so many people, so badly in trades, going back so many years that I was afraid of him......he could have offered me more then that and I wouldn't have dealt with him...I was too afraid to deal with Red."