Jeff Gray's legal career is highlighted by several significant victories. One notable case involved his arrest in Alpharetta, Georgia, where he was charged with panhandling while holding a sign supporting homeless veterans. With the help of the Foundation for Individual Rights and Expression, Gray argued that the city's panhandling rules violated free speech protections. The case was settled, with Alpharetta agreeing to amend its policies and provide training for law enforcement on First Amendment rights. This victory not only secured a financial settlement for Gray but also led to meaningful changes in local policies, demonstrating his ability to achieve tangible results through legal advocacy.