Why did Milo Ventimiglia leave Gilmore Girls?

Regardless of your feelings on the popular “Literati” ship comprised of Alexis Bledel’s Gilmore Girls character Rory Gilmore and Milo Ventimiglia’s bad boy Jess Mariano, most fans can agree that Jess’ character was a welcome addition to the cast. Whether you were rooting for Rory and Jess to be together or not, Jess brought some much-needed conflict to Rory’s love life and real competition for her affection.

It didn’t hurt that Bledel and Ventimiglia had obvious romantic chemistry from the start. The two even dated off-screen for several years after meeting on the show. But Jess doesn’t end up sticking around as long as many fans would have liked and eventually, literally, gets put on a bus out of town.

Entering the show in season 2, Ventimiglia was on Gilmore Girls as a series regular throughout the second and third seasons. He was in 37 episodes overall, but the bulk of his screentime was split between those earlier seasons when Jess’ mom, Liz, shuttled him to Stars Hollow to become his Uncle Luke’s problem.

A Jess-centric spinoff series was once in the works

At the end of the third season, Jess leaves town to go live with his dad in California after everything goes downhill between a fight with Dean and flunking out of school and not being able to take Rory to prom. Reports say that Gilmore Girls creator Amy Sherman-Palladino was a huge fan of Ventimiglia, so there were plans to make a spinoff revolving around Jess happen.

Even before the spinoff idea came around, Sherman-Palladino reportedly offered the actor a lucrative multi-year contract, but he supposedly turned it down in favor of just appearing on the show when time allowed.

In short, Ventimiglia enjoyed his time on the show and working for Sherman-Palladino, but also didn’t want to be tied down at the time with a multi-year contract. He would later return for the Gilmore Girls revival and work with Sherman-Palladino again on her show The Marvelous Mrs. Maisel.

If the spinoff had succeeded, then we would have gotten to see how Jess grew and changed while living with his dad on the west coast. But unfortunately, Warner Bros. felt that the spinoff was too costly and ended up canceling their plans for a six-episode run.

Even though the spinoff didn’t work out, Sherman-Palladino was happy to leave the door open for Ventimiglia to return, which is why Jess comes back several times throughout the rest of the show, though never more than for a few episodes at a time. His final appearance in the main show was in the season 6 episode, “The Real Paul Anka.”

He notably didn’t return for season 7. According to reports, Ventimiglia wasn’t happy when The CW replaced the Sherman-Palladino and her husband Daniel Palladino. That’s why he did return for the Netflix revival, because it was the showrunner’s original vision.

What did Milo Ventimiglia think of the Jess and Rory pairing?

In 2021, Ventimiglia visited Scott Patterson’s (who plays Luke Danes on the show) podcast, I’m All In, and discussed the fan-favorite pairing. It seems like Ventimiglia appreciated the couple and their ability to make “their own world” despite many people rooting against them, but overall he was fine with them not ending up together.

"“I think [Jess and Rory] were what they needed from the moment, from each other and at the same time, it didn’t work out. They went in different directions. And that’s OK too. That’s kind of great.”"

At one point, Ventimiglia told E! News that he lobbied for his character to get killed off.

"“I was the one who actually tried to get [the character] Jess killed, and they didn’t go for it. [I wanted to] get him hit by a bus, a knife in the side of the neck, something bad. [Laughs.] I don’t know–guess I thought it would be kind of cool.”"

Interestingly, in that same interview, the reporter asked Ventimiglia if he would ever come back to the show. The E! News interview was published in September 2006, which was right around the time season 7 started airing.

Him saying he would return if invited goes against the reports suggesting he didn’t want to come back without Amy Sherman-Palladino, but perhaps the interview took place months before and was held until September, before Ventimiglia knew what happened behind the scenes at The CW. Or he was just being polite.

So, in short, it seems like Ventimiglia was always planning on a shorter visit to Stars Hollow than the other regulars at the time, and appreciated that he could come and go between his other jobs. In 2006, he was cast in a leading role on the NBC superhero series Heroes as Peter Petrelli and then would later go on to star in the acclaimed series This Is Us, a show that earned him multiple Emmy nominations.