Wouldn't a Real Estate Investment negate the Capital Gains tax, just a little?
@truth_seeker
I simply asked you if you could explain the angle, since you implied there was one.
Based on what I know about taxes, no. A payout realized from a parachute would not be offset, by a real estate purchase.
Since he is quite wealthy, he needs diverse buckets in which to store his wealth. In recent years (since 2006) buying property has been a good investment. But now might be another peak of the market.
He will later pay taxes from "realized" gains, from both securities and real properties. Some of the costs of maintaining those investments, will offset the gains, if any.
I'm not a tax attorney, so get professional advice. Since he is quite wealthy, he can afford the best tax advice and investment options that there is/are.