Has there ever been a character who exists in life’s moral gray area more than Jimmy McGill? On Better Call Saul, he’s the protagonist with big dreams and a bigger heart who can never quite achieve his goals by playing it straight. Often Jimmy has to resort to what he’s best at — being a showman and a swindler — in order to achieve his bottom line. While this can sometimes be for selfless purposes, every scam and scheme pulls him further away from the good man he is deep down.

Let’s delve deep into this complicated lawyer’s best and worst moments as we explore Jimmy’s descent into becoming Saul Goodman.

Best: Cares more about Chuck than his own celebration

Jimmy and Chuck McGill are two of the most dysfunctional brothers in television history, but they sure have their loving moments, too. In a flashback scene, Jimmy celebrates becoming a lawyer at a dive bar with Kim and a few HHM employees. Chuck comes along out of sheer obligation, as evidenced by him sitting awkwardly by himself and clearly having a miserable time.

Jimmy coaxes Chuck to join him for a karaoke rendition of “The Winner Takes It All.” The duet quickly becomes a showstopping solo as Chuck embraces his inner performer. This day was one of the biggest moments of Jimmy’s life, yet all he wanted to do was draw his brother out of his shell.

They say that opposites attract, and that sentiment couldn’t be more true for Jimmy McGill and Kim Wexler. Whereas he’s all about shortcuts and backdoor strategies, Kim is always on the straight and narrow. Yet both lawyers struggle to get the professional recognition they deserve.

After Kim quits Hamlin, Hamlin & McGill to start her own practice, she hits a crippling roadblock when her only potential client, Mesa Verde, decides to stay at her old firm. Out of love for Kim, Jimmy intentionally sabotages Chuck’s legal documents for Mesa Verde to make HHM look bad. Jimmy’s plan works and Kim wins her rightful client, but this only happened because Jimmy royally screwed over his brother.

Best: Continually shows his love for Kim

Not all of Jimmy’s affection for Kim is demonstrated by breaking the law. He may do his best work as a charlatan, but Jimmy is also one heck of a boyfriend. When the overworked Kim falls asleep at the wheel, breaking her arm in a major car accident, Jimmy drops everything to take care of her. He wants to help Kim find success and happiness in any way he can, even if his efforts cause a rift in the relationship when the couple finds themselves at opposite ends of the ethical spectrum.

Worst: Scams people for sport

Jimmy is usually breaking the law or the rules in one way or another. As established, most of the time this is for a noble reason. But Jimmy has to admit it — scamming people gives him an adrenaline high that nothing else ever could. Before he became a lawyer, he earned the sleazy nickname of Slippin’ Jimmy based on his proficiency at cheating people out of their money by running slip and fall con jobs.

Even while practicing law, Jimmy can’t resist the pull of the swindle, especially when he’s at a low point. For fun, he and Kim target white-collar barflies, enjoying top-shelf liquor on their mark’s tab. And if he didn’t have Kim to rein him in, we all know that Jimmy would have scammed his rubes out of more than just quality hooch.

Best: Fights for the elderly

When we first meet Jimmy, he’s barely scraping by as a public defender. But he soon finds his stride in elder law. Jimmy knows when he’s spotted a fellow con artist, so when he discovers that Sandpiper Crossing, a retirement home, is illegally turning their residents into cash cows, he convinces them to file a class-action lawsuit.

This is probably Jimmy’s highest point in his career. Not only has he found honest work, but he excels at what he does. What’s more, Jimmy takes pride in helping these seniors find some justice. In a society that treats the elderly as a problem to be solved or worse, ignored, Jimmy truly makes a difference.

Worst: Manipulates Irene in the cruelest way possible

While Jimmy may have a soft spot for the elderly, he’s not above selling one of them down the river when it comes to his own personal gain. Strapped for cash, Jimmy discovers he could come into a huge payday if the Sandpiper Crossing case settles. The only problem is resident Irene, who is holding out for more money.

In the most glaring example of taking things too far, Jimmy ruthlessly turns Irene’s friends against her in an attempt to get her to settle. Watching this poor sweet lady’s heart break as she’s shunned by her besties is gut-wrenching to watch. Sure, we’re along for the ride when Jimmy’s scamming arrogant businessmen, but this is just too much.

Best: Goes out his way (literally) to help Huell

Jimmy may have little regard for many people, but when somebody is loyal to him, he sure returns the favor tenfold. After Huell gets into serious trouble with the law by trying to help Jimmy out, Jimmy goes above and beyond trying to right this wrong.

Huell retains Kim as his lawyer and she finds it impossible to get him a plea bargain. So she convinces Jimmy to travel to Huell’s hometown and create dozens upon dozens of letters in fake support of Huell. Jimmy even goes the extra mile, so to speak, and plays the parts of Huell’s supporters on the phone, convincing the judge that if he takes Huell to trial, he’ll have a full-blown disruptive protest on his hands. Sure, this particular plan is Kim’s idea, but Jimmy is more than game to do the legwork.

Worst: Drives Chuck to suicide

Jimmy’s little stunt in tampering with Chuck’s legal documents finds his big brother seeking revenge. The result is Jimmy having to go to trial, facing possible disbarment. To prevent this from happening, Jimmy stages an elaborate scheme in which he makes Chuck look mentally unstable in front of everyone in the courtroom.

The plan partially works and Jimmy is suspended from practicing law for one year. But when he’s faced with a steep insurance bill and no income to pay it, Jimmy seeks revenge by letting Chuck’s mental condition slip to the insurance company. Jimmy succeeds in dragging Chuck down with him, as the older McGill brother has no choice but to retire from HHM. Chuck defined himself as a lawyer, so now that he’s no longer working or even able to leave the house, he decides to end it all. He intentionally sets fire to his home and dies in the blaze, all because of Jimmy’s actions.

Best: Takes care of Chuck

Despite Chuck meeting his grisly end because of Jimmy’s vengeance, Jimmy spent a good chunk of his life being a doting brother. When Chuck confines himself to the house due to his electromagnetic hypersensitivity, Jimmy becomes his personal assistant and errand boy. He does whatever Chuck needs or wants, all without complaint.

But in spite of Jimmy’s loyalty, Chuck has always looked down his nose at his brother. Chuck is a man who prides himself on doing things by the book and resents when Jimmy achieves the slightest modicum of success through unconventional means. Even though Jimmy legitimately makes himself a lawyer, Chuck sabotages his career and prospects at HHM. Even after discovering this betrayal and severing ties with Chuck, Jimmy goes back to help his brother when he thinks he’s gone off the deep end.

Worst: Becomes Saul Goodman…the lawyer

The first time audiences ever met Jimmy was as Saul Goodman, the criminal lawyer on Breaking Bad. Throughout Better Call Saul, we kept wondering when Jimmy McGill would transform into his fast-talking alter ego.

Jimmy fails to be reinstated as a lawyer because the board found his sorrow over Chuck’s death to be disingenuous. Jimmy spends the next year publicly trying to show the world — really, the board — the profound effect the loss of his big brother had on his life. The pièce de résistance is Jimmy crying crocodile tears at his second hearing, conning not only the board but Kim as well. Fully reinstated as a lawyer, Jimmy ditches his name…and the last shred of his morality.