Witness Larry King, he only managed to get $25Million before he couldn't get any more. His annual income is around $14Million.
You could probably *apply* for that insurance, but you'd have to have a pretty good reason for insuring the insured entity for that much, and there would have to be ways for the insurance company to determine what the risks were. Most insurers will only allow you to insure something that hefty for its actual value, current or future, on a year-by-year basis, rather than its speculated cumulative value
e.g. if you were applying for a disability policy for a *very* high-paying job, the insurer might want to know about your general health and to place terms on your policy (e.g. the policy only pays out if you become medically disabled, not if you "disappear").
Probably not.