Wes could have signed something like a 1 yr $5M deal (or whatever necessary to retain Bird rights, say with team and/or player options), been fully embraced by the fan base, and signed for a much bigger deal a year later with the new TV contract. He would probably have come out ahead financially and not tarnished his reputation for cashing in at the expense of the team.
Yes, it's a bit of a gamble that he never gets healthy enough to get the big contract. But, a) would you be happy in that position, being someone that millions of people despise? and b) for someone like Wes who had absolute certainty he would come back healthy this year, the risk should have been a very minimal concern.
Y'all can say whatever you like about Wes being a great guy. The fact is, he is a typically greedy professional athlete who put his bad health ahead of the team's good health financially. It's no wonder that the owners try to shaft the players whenever the CBA is up for renewal, if even the "good" ones are like that.