Even in a large cast full of colorful characters portrayed by the best comedians in showbiz, Jack Donaghy (played with sardonic charm by Alec Baldwin) routinely stole the limelight on Tina Fey’s hit comedy series 30 Rock. As the self-possessed Vice President of East Coast News and Microwave Oven Programming for General Electric, he was a charming suit who loved truth, capitalism, and the American Way. Presiding over the writers and talent of the sketch show TGS, he dispensed his pearls of wisdom while swirling a glass of scotch in his hand.

As helpful as it was for Liz Lemon and the other writers or Tracy Jordan and the other talent to have Jack step in and help them sort out their daily trials, his advice was often offensive, insensitive, and selfish. His actions throughout the series often made him come across as a corporate shill for whom avarice and ambition were the only worthy pursuits. Below you’ll find the 10 worst things Jack Donaghy has ever done.

RAN OVER HIS MOTHER WITH HIS CAR

Perhaps it’s because Colleen Donaghy left his dog Pop to die after being run over by the mailman. Perhaps it’s because she traded sexual favors in exchange for presents to give him on Christmas. Perhaps it’s because she blamed him for the death of JFK or because she’s nagged him every year of his life since he was born, but Jack Donaghy ran his mother over with his car and didn’t even feel sorry about it.

Jack failed to spring into action with his usual gusto, even failing to call emergency services for several minutes while she lay in his driveway. Of course, it was later ruled an accident, but that didn’t stop him from wishing her dead when all was said and done.

REPLACED JENNA MARONEY WITH TRACY JORDAN ON TGS

Liz Lemon and Jenna Maroney are best friends, and TGS (The Girlie Show) was initially started as a vehicle to showcase Jenna’s acting, singing, and improv talents. Of the two of them, Jenna was always the beauty and Liz was always the brains.

When Jack became the Vice President of East Coast Television and Microwave Oven Programming, he directly oversaw TGS and immediately made crazy and charismatic movie star Tracy Jordan the show’s lead. While an intrinsically smart move, it created a tense set and constant jealous feuding between Jenna and Tracy.

GOT ENGAGED TO PHOEBE

Despite being known for making shrewd business decisions and cleaning up corporate messes, Jack’s laissez-faire attitude towards his dating life has meant unscrupulous women have wormed their way into his heart and bed. On the advice of his idol Don Geiss, he started to date Phoebe, an auctioneer at Christie’s, even though Liz warned him against it.

The fraudulently delicate Phoebe proved to be a nefarious gold digger, who was only after Jack for his power, prestige, and money. Even after Liz’s protestations, Jack proposes to Phoebe, and the engagement is only waylaid when he has a heart attack. After a conversation with Liz and his mother in the hospital, he realizes he’s not in love with Phoebe at all.

HAD SEX WITH NANCY WHILE DATING AVERY

Despite having mixed feelings about his on-again-off-again relationship with Nancy, his high school crush (played by Julianne Moore), Jack decides to pursue something romantic when she becomes recently divorced. He sleeps with her even though he’s recently been seeing Avery Jessup, a prominent CNBC anchor.

Nancy runs into Avery on accident and discovers that she’s pregnant. It’s Nancy who breaks the news to Jack, who is completely blindsided. Complicating this is the fact that he accidentally gets himself hitched to Liz Lemon instead of Avery because the officiant didn’t speak English.

CRASHED LIZ LEMON’S HIGH SCHOOL REUNION

Though having Jack Donaghy as her date to her high school reunion might have ruffled a few feathers in Liz Lemon’s favor, that’s not how he ended up there. He offered to drop her off in the company plane while he went to greener pastures, but bad weather forced him to be grounded in her home town.

Since Liz is from a dry county, the only bar available to a functioning alcoholic like Jack was the open bar at the reunion. He crashed the affair and posed as an alum, instantly ingratiating himself to her friends. Eventually, Jack was found out, causing him and Liz to be run out of the hotel.

USED TRACY JORDAN TO GET HIS BOSS’S JOB

Before it was made official that Jack’s idol Don Geiss was about to step down as CEO of General Electric, Geiss hinted that he would select him as his replacement. But Jack’s position wasn’t immediately secure - it would have to be approved by a board of directors first.

In order to butter Geiss up, there was a period of time when he paraded Tracy Jordan around him in an effort to showcase the prestigious individuals he rubbed elbows with. Unfortunately, Jack using Tracy for his own agenda backfired when Tracy went full Tracy on everyone.

GOT RID OF KAYLIE HOOPER TO TAKE OVER KABLETOWN

When Kabletown took over NBC and directly oversaw TGS, Jack had to amend his desire to become CEO of General Electric and instead focus on becoming the CEO of Kabletown. Just one thing stood in his way - Kaylie Hooper, the granddaughter of Hank Hooper, the resigning CEO of Kabletown.

In a diabolical game of cat and mouse, Jack deliberately sabotaged Kaylie’s chances of playing lacrosse at her dream university, as well as any hope she ever had of being CEO of Kabletown by feigning more concern about her grandfather’s birthday than she did.

MADE OUT WITH AVERY’S MOTHER

It was wonderful to see Mary Steenburgen guest star on the show, and her presence caused more sparks between her and Jack than a Trivection Oven on the fritz. However, as the mother of Jack’s girlfriend Avery, their chemistry was as inappropriate as it was undeniable.

Avery had been kidnapped and kept against her will in North Korea. While Jack and the UN negotiated for her release over the course of a year, he and Diana (Steenburgen) were drawn together over their grief and mutual hatred of Prius drivers.

TRIED TO MEDDLE IN LIZ’S DATING LIFE

When Jack was first brought in to oversee TGS, Liz hated him and the feeling was mutual. Over time, they developed a begrudging respect for each other’s abilities and eventually, the domineering suit and the quirky creative became the best of friends.

Jack liked nothing better than to dispense pearls of wisdom with a tumbler of scotch in his hand. His ideas rarely afforded him any success (though MILF Island was a hilarious premise for a reality show), but where he shined was his ability to read people. This meant he constantly interfered in Liz’s love life, especially in the early days when she dated Floyd, and later when she briefly dated the new TGS talents Danny and Criss Chros.

MADE KENNETH TRY TO SEDUCE BANKS

In the dog-eat-dog world of corporate capitalism, Jack Donaghy was king as the Vice President of East Coast News at NBC. The only man that ever posed a threat to his throne was Devon Banks, Vice President of West Coast News and Jack’s nemesis.

In planning how to best overthrow his enemy, Jack decided that his best course of action was to analyze Banks’ weaknesses and exploit them. Openly gay, his greatest crutch seemed to be his libido, so Jack deduced the best plan was to make earnest page Kenneth Parcell seduce Banks and learn his plan to take Jack’s job.