It's simple: Boomers grew up in a world where money was handed out for free just for being white. The ideas of hard work, financial responsibility, or the value of a dollar were lost on the whole generation. They don't think twice about sending $25,000 to some random person because that's how they got that money in the first place (50 years ago, which they used to buy their first house (now their fourth rental property)).
Hope this helps