When your philanthropy is just enough to offsett your taxes and you still get to make money off of the assets you donate until the term of the trust expires, then is it really philanthropy? Not to mention, a lot of the time the "charity" they donate the assets to are run by them indirectly, and it's then impossible to track where the money goes after that.

Donate your stock to a charity through a trust before you sell it. You get a tax break that year for the donation. The trust sells the asset and is tax exempt so no capital gains tax. You take 5% every year as that amount appreciates from investing it. Only pay regular income tax on that which you wrote off with another "donation". Make your money back over 15-20 years, then make a profit until the trust expires, or you do and then your kids make the profit. Charity gets whatever is leftover after the trust term expires.

Just one example of why "philanthropy" is usually still making profit for them, maybe slightly less profit in some cases than they could have made with it otherwise, but considering they already have more money than the next 100 generations could possibly use, it's just a small price to pay for the PR.