Conversation so far:
Did Randy Moss always play sports?
In addition to excelling at sports, Randy Moss was also on the school's debate team while at Riverside High School.
Did anyone in Randy Moss' family play sports as well?
Randy Moss' half-brother, Eric, had played offensive tackle at Ohio State University, and had a short stint in the NFL as an offensive tackle with the Minnesota Vikings.
Did Randy Moss ever have aspirations to be in a specific pro team?
Randy Moss grew up a Cowboys fan and wanted to play for the Cowboys.

Question: Was his past always troublesome
Self-contained rewrite: Was Randy Moss' past always troublesome?