Hindsight? I called it immediately when it happened. And then in my former incarnation, I reported running into Clifford Ray, former teammate of Jerry with the Bulls at LA Fitness in Orlando -- Ray still works as an assistant coach from time-to-time. Well, Ray said Jerry, who he talks with regularly was p'o'd about the refusal to match Portland. And we all know, so was DWill. And like AKMVP said, this decision led to the chain reaction that resulted in Jerry quitting and Deron being traded (DWill had been becoming increasingly disenchanted with the moves of the front office, and the failure to retain Matthews was the last straw).
I think a good basketball evaluator could tell from his first season that the guy was going to be a player. He had heart, speed, and was a clutch player, as well as an excellent defender. I liked him early on and said as much, just like I spotted the same regarding DeMarre when everyone else on here insisted he was a scrub. Signing him would've kept the Jazz in the playoffs every year because Jerry would still be the coach and DWill would be our PG.