In Breaking Bad‘s pilot episode, viewers get their first taste of Jesse’s money management skills (or lack thereof) when Walt trusts the younger man with a few thousand, to buy an RV suited for meth-making. Jesse takes full advantage of Walt’s misplaced faith to go buck wild (literally) at a local strip club. Jesse does get an adequate RV from a friend, for a sliver of Walt’s funds… but it’s the principle of the thing.
Jesse’s history of drug usage thins out his wallet, too. Especially in earlier seasons, he has a tendency to lose himself in drugs whenever he’s stuck in a rut. Jesse enters one of these downward spirals after Combo (Rodney Rush), the friend that sold him the aforementioned RV, is killed. Jesse’s girlfriend Jane Margolis (Krysten Ritter) is able to blackmail Walt into giving Jesse a share he’s owed, but after her own drug-induced death, Jesse sinks to one of his lowest points, money or no money.
Though Jesse’s non-stop house parties in season four surely cost him a bit, season five showcases his biggest money moment (and one of his most well-known moments in general). Walt gives Jesse what he’s rightfully owed: a whopping $5 million, cash. Stuffed into duffel bags, Jesse just can’t accept the money, knowing the horrible things — betrayal, murder, and worse — that brought it about. He drops it off with Saul Goodman (Bob Odenkirk), who gives it back to Walt, who finally gives it back to Jesse. As if he needed any more convincing of what an endless cycle a life of crime can be.
Fed up with everything, Jesse drives out into town, money in tow, and falls asleep in a parking lot. A homeless man wakes him up asking for spare change, and Jesse makes a decision right then and there: he’s going to get rid of the blood money, once and for all. Handing the homeless man a wad of bills, he shifts his car into gear and drives around aimlessly, tossing the rest of the wads out the window one by one. The emotionally-fueled decision may not help him by the time of El Camino, but watching the scene… it feels right. Becoming top dog stopped being a priority long before, and Jesse had to do what he felt was best.