The great trick of Breaking Bad, Saul Goodman, into one of the most relatable characters of either show, Jimmy McGill. The show does this by never sugarcoating Jimmy's most immoral deeds but also showing how they ultimately just hurt him and those he loves, even when his schemes succeed.
Jimmy's worst schemes, therefore, are often some of his best, from another perspective. Jimmy is a character who very often gets exactly what he wants, but what he wants is to be self-destructive and avoid his problems. The series finale shows just how heavily all of these decisions weigh on him, and the audience feels the pain of his mistakes along with him.
Selling Drop Phones On The Street
After Chuck gets Jimmy's law license suspended for a year, he takes an interim job at a phone store, but this is mostly to take Jimmy's mind off of Chuck's death. Predictably, the job is far too boring for Jimmy, and he feels the irresistible urge to bend the rules.
Jimmy decides to buy a bunch of the store's prepaid phones and sell them on the streets to people looking to make untraceable calls. Not only does this get him mugged on his first night out, but his further obsession with selling the phones on the street leads to him developing s as his alter ego, Saul Goodman. It's a stepping stone in the creation of Jimmy's most destructive persona.
Trying To Con Betsy Kettleman
In the first episode of the series, the audience is introduced to both Jimmy McGill the struggling lawyer and Slippin' Jimmy, conman extraordinaire. Slippin' Jimmy's first ultimately self-damaging plan comes in the form of a staged hit-and-run which Jimmy wants to use as leverage for securing the mark, Betsy Kettleman, and her husband as clients.
Of course, nothing goes to plan and Jimmy's young accomplices pick the wrong car, leading both them and Jimmy to the home of Tuco Salamanca's beloved abuelita, where Tuco is waiting to hogtie them and drive them out to the desert. Though Jimmy talks his way out of this situation, even saving the lives of his two accomplices too, it introduces him to both the Salamancas and Nacho Varga, who suck him deep into the criminal underworld of Albuquerque.
Making A Commercial For Davis & Main Without Permission
Attempting to play things straight as a lawyer and take a steady job at a well-respected firm, Davis & Main, Jimmy works on the Sandpiper Crossing case through the firm but finds Chuck hawkishly watching him at every turn. After already bending the rules about soliciting seniors, Jimmy seeks to sidestep Chuck's attempts at limiting his tactics by making a TV commercial for Davis & Main and the class action suit.
Overall, it's a decent idea but Jimmy, either fearing interference from the partners at the firm or just being impatient, makes the commercial and then runs it on live TV without telling any of the partners. Worst of all, he strongly implies to Kim that he okayed the ad with the partners at Davis & Main, making her culpable for his effective-but-tacky commercial and the fury it causes. Not only is this the beginning of the end for Jimmy's by-the-book life at Davis & Main, it introduces him to the world advertising, another key aspect of Saul Goodman.
Directing Commercials To Resell His Ad Time
Long after his advertising incident at Davis & Main, Jimmy returns to TV advertising, this time selling himself and his solo practice. But after his feud with Chuck results in Jimmy losing the ability to practice law for a year, Jimmy is left with a bunch of useless ad time that can't be resold. Pinching his pennies in an attempt to keep his shared office space with Kim afloat, Jimmy decides to become an ad director, charging small businesses for shooting new ads for them and giving them the airtime for free. The scheme finds a way for him to effectively resell his airtime legally, but it's riddled with issues.
It's a desperate move to begin with and reeks of all the untrustworthy qualities that make up Jimmy's business life before becoming Saul Goodman full-time. Not only does it run Jimmy ragged all over town, netting him virtually nothing in the end, but it also furthers his relationship with a small team of students who become some of his most important accomplices for his later crimes.
Convincing Irene Landry's Friends To Turn On Her
After finding out about the huge sum of money that he stands to gain from the Sandpiper Crossing case once its finished, Jimmy attempts to manipulate the sweet elderly class representative, Irene Landry, into settling.
Jimmy is successful in his subtle scheme to slowly poison the image of Irene within her close-knit retirement community, all but forcing her to settle in an attempt to win back favor. However, this is just too inhuman for even Jimmy's tastes, and he engineers a situation where he gives a staged public confession. This exonerates Irene but destroys Jimmy's chances of ever working in elder law again, something that he was actually quite good at.
Switching The Numbers On Chuck's Documents
Even though Jimmy breaks the law in many elaborate ways throughout the series, his worst decisions are the ones that he makes early on in the show regarding his brother, Chuck. The things that he does to Chuck often don't appear to be illegal in any way, but they're somehow morally indefensible. The first of these starts out small, but snowballs into much worse events.
After Kim attempts to take the client that she secured for her old firm with her when she leaves and looks to be successful, Chuck goes out of his way to snatch them back. Jimmy, believing this is really an act designed to hurt him through Kim, enters Chuck's house while he's ed out and doctors some of his business documents. Jimmy is successful in causing an embarrassment for Chuck that gets the client back with Kim, but it begins a new phase of his rivalry with Chuck that ultimately breaks their relationship and gets Jimmy suspended from practicing law for a year.
Meddling In Chuck's Malpractice Insurance
Chuck's death was one of Better Call Saul but, as is always the case with Breaking Bad and Better Call Saul, it's clear with hindsight that it was a moment that had long been built up to. In the war between Chuck and Jimmy, Jimmy's final blow to his brother is to meddle in his malpractice insurance.
At the time, it seems like a small act of pettiness that will simply inconvenience Chuck's life further. However, whether by accident or design, it also has the consequence of driving a wedge between Chuck and Howard Hamlin. The standoff results in Chuck being forced into retirement as well as the rapid psychological deterioration that he experiences before his death. It's clear that Jimmy knows that he played a larger role in his brother's death than Howard did, but deflects all blame onto Howard anyway. Jimmy's final confession in the series finale makes it clear that the consequences of this act broke him more than any other.
Being Lalo's Bagman
One of Jimmy's worst choices on the show has to be his decision to escort Lalo's bail money from the Mexican border to the courthouse. It's possible that Jimmy was terrified of not doing what Lalo had asked of him and doesn't believe that Lalo is really okay with it when he refuses. If that's the case, however, it makes his ploy of walking away to get an extra payday from Lalo all the worse.
Jimmy is almost immediately ambushed on his way back from collecting the money which leads to a bloody shootout between his robbers and Mike, a traumatizing walk through the desert, and Lalo getting introduced to Kim. If Jimmy had listened to Kim and walked away from the deal, a lot of tragedy may have been avoided.
Stealing From Lonely Men At Bars With Jeff
After the events of Breaking Bad, Jimmy lives a quiet life in Nebraska as Gene Takovic before being recognized by Jeff, a cab driver who once lived in Albuquerque. Instead of running again, Jimmy makes the decision to buy Jeff's silence by helping him plan and execute a crime. Then, after becoming incensed by a call to Kim, Jimmy falls back into his conman ways and uses Jeff and his friend in a number of criminal schemes. They ply a mark with alcohol before drugging them and photographing their personal and financial documents, presumably for identity theft.
The idea, when functioning exactly as it should, comes across as fairly slapdash to begin with, as there's plenty of opportunity to get caught. But, after losing one of his accomplices, Jimmy steps in and breaks into a mark's house behind schedule. Jimmy is practically begging to be caught at this point, and it's quite sad to see him tempting fate at every turn. Naturally, this is the scheme that ultimately gets him caught by the police.
Antagonizing Howard
To some extent, Better Call Saul is a show about Jimmy McGill ing all of his past mistakes, all of the points where he should have gone left but went right instead. His relationships with Chuck and Kim are a huge part of what makes up the persona of Saul Goodman, but one of the major regrets of Jimmy's life is his relationship with Howard Hamlin.
Howard is Chuck's closest ally, so naturally he and Jimmy start out at odds. After Chuck's death, Jimmy has the opportunity to bury the hatchet with Howard for good but instead chooses to antagonize him, much like Chuck did to Jimmy. After embarrassing and harassing Howard, he then plots with Kim to discredit him as a lawyer in order to finally get Sandpiper settled. This results in Howard being at Kim's apartment when Lalo arrives there, with Howard then being murdered. In many ways, Howard was Jimmy's only real friend other than Kim and a better candidate to be his brother than Chuck. Jimmy didn't just ruin Howard, he ruined himself and his own chances of being happy.