The one big red flag for Ainge must be Bradley's health issues in past years. Bradley has improved every season, and his offense this year was a big leap for the restricted free agent. Bradley ended the season with a season average of 14.9 points per game. That's 5 points higher than his career high of 9 points a game during the 2012-13 season.
If it was my choice, I would offer AB 4.5 million a season. That's because of his injury history. Avery at 6 million could be a steal if he's able to play nearly almost every game.
In most years, unrestricted free agents are a good bet to return to the team that holds their matching rights. But when Bradley and his camp broke off extension talks with the Celtics over the winter despite the fact that the sides weren’t far apart, the guard may also have lost out on his best-case money scenario for next season.
Bradley’s ongoing brittleness considered, the C’s are unlikely to return to the four-year, $24 million extension that was previously offered. The injury issue may also limit what he finds on the market this summer.
The market could go either way for Bradley. This is a weak free agency class, so anything can happen. Bradley is only 23 years old, and he continues to get better on the offensive end. So maybe he's worth the risk.