In a way it seems like he wants more money rather then more rings. And big deal if he's in the gym everyday, I'm in the gym everyday playing and putting up j's to get better for my upcoming freshmen year, just matters on what he's working on, how long and if it shows up this fall,winter,spring and hopefully summer.
How old his he? My first concern would be getting paid too. Take care of myself and my family, and then go for the rings. Anyone who says they wouldnt do the same is a liar.
If he was wise with his money he has ALREADY taken care of his family for life, given that he's already made > $5MM in his career. And, if not, with ANY contract he signs next, whether it be for $8MM per or $15MM per, his family will be set for life. So, to think that he'll be more happy with $15MM per year playing on a lotto team, vs. $10MM for the C's with yearly title hopes, is not lying. It's just priorities. I, for one, have made the decision years back to stop climbing a management track and to pursue a career path where I'm making way less money ... cause I'm enjoying it way more.
You can't compare your situation to Rondos for a variety of reasons.
One is that, on a winning team, there is more expectations and pressure, and he'll have to work harder. I imagine in your situation, that was your "management" route. While, if he goes to a lottery team and gets a big pay day, he'll have less pressure, less media, & less expectations for winning - and making more money. The opposite of your situation.
One could argue- that you did not chose the "winning team" - of working hard and becoming management, but instead your in the stress free life of the lotto team. (money aside)
And after a rookie contract- he'll need a lot more to take care of his family with the expensive NBA lifestyle, full of mansions and cars. A lot of players end of broke after their career - albeir their irresponsible, but still - there's a reason you dont have every all star playing for the minimum to win.