Maybe, but the American tax system seems unreasonable complicated and trickable with its 'charitable foundations' and 'Donor-advised funds'. I think it's rather defeatist to think it's impossible to make a better and less exploitable system.
Of course, we are now entering the time of open oligarchy, so it probably won't happen soon.
I suspect the US tax system has far more smart people working on generally finding and exploiting its features and other holes and optimizations than your favorite OS or bloated web browser.
Of course, we are now entering the time of open oligarchy, so it probably won't happen soon.