This is a beautiful man. I dont have the pleasure of living close enough to be part of Dr. Gil's sangha, but I am very grateful that a very wise person created audiodharma.org so that we can enjoy all of his talks and those of many other teachers.
The West offers happiness, favorable external events. Buddhism offers peace, transcending the happiness or unhappiness. Letting go is accepting the world as it is, not as I wish it to be.
Norman Fischer also likes to say that zen practice just comes down to "don't make it worse." I know the two teachers have spent time at San Francisco Zen Center, I'm guessing they practiced together too :D
Who could possibly feel good if they listen to the news? Only bad news is good news. If it bleeds it leads. We are macabre. But letting go is not happiness. Letting go is peace. Big difference. Buddhism offers peace, NOT happiness. Happiness is different.