To be honest, I think Howard is fairly within his rights to want another max contract.
I mean seriously, look at the type of money people are throwing around to bigs these days. Tristan-bloody-Thompson got a ~$17M a year max deal, and he is a straight up role player.
DeAndre Jordan got a $20M/year max deal and had two teams fighting over him despite that.
What Dwight Howard brings is really not that far off what DeAndre Jordan brings. Dwight is a comparable defensive player and a comparable rebounder, but is a significantly better offensive player.
The age and injury history obviously hurt, but he's still a 14/12 guy with elite defensive ability, and it's pretty hard to argue against that being max-contract worthy. Especially at a time when every team has cap space to burn.
Dwight has his issues, but he can still do a LOT to help a team, and he's got at least another 3-4 years of good basketball left in him, assuming his back doesn't give out. If it does then he likely retires, in which case that contract is void anyway.
I'm just imaging a starting five of Thomas, Bradley, Crowder, Simmons and Howard with Smart, Turner, Jerebko, Amir and Olynyk on the second unit. That would be one hell of a team!