Since the 2018 Supreme Court decision overturned the federal ban on sports betting, it has spread to 39 states and D.C., driven by mobile apps and deep partnerships between gambling companies and sports leagues. While states benefit from new tax revenues, the ease of access has led to rising addiction rates and financial ruin for individuals like Kyle, whose story illustrates the dangers of always-on betting platforms. Though marketed as harmless fun, these apps are engineered for compulsive use. Meanwhile, professional gamblers profit not through luck but by exploiting market inefficiencies, while sportsbooks limit winners and rely on chronic losers. The expansion into prediction markets and financialized apps further normalizes gambling behavior, especially among younger users, with minimal regulatory safeguards. Despite growing concerns over integrity, mental health, and equity, political and financial incentives hinder meaningful reform.