The NY Times reports that former House Speaker Hastert made his money legally:
After Speakership, Hastert Amassed His Millions Lobbying Former Colleagues
"From 2011 to 2014, Lorillard Tobacco paid Dickstein Shapiro nearly $8 million to lobby for the benefit of candy-flavored tobacco and electronic cigarettes, and Mr. Hastert was the most prominent member of the lobbying team."
After Speakership, Hastert Amassed His Millions Lobbying Former Colleagues
"From 2011 to 2014, Lorillard Tobacco paid Dickstein Shapiro nearly $8 million to lobby for the benefit of candy-flavored tobacco and electronic cigarettes, and Mr. Hastert was the most prominent member of the lobbying team."