This review explores popular gambling strategies often believed to guarantee wins, such as card counting and taking advantage of arbitrage. We present a mathematical overview of these systems to evaluate their theoretical effectiveness in ideal conditions by presenting prior research and mathematical proofs. This paper then generates results from these models using Monte Carlo simulations and compares them to data from real-world scenarios. Additionally, we examine reasons that might explain the discrepancies between theoretical and real-world results, such as the potential for dealers to detect and counteract card counting. Ultimately, although these strategies may fare well in theoretical scenarios, they struggle to create long-term winning solutions in casino or online gambling settings.