A Stockton city leader appears to have found a new NBA crush years after a public encounter with Kelly Oubre Jr. didn’t go as he had imagined. What started as a bittersweet storytelling session eventually turned into a new name-drop. The man at the center of the story is Jason Lee, Stockton’s vice mayor and a longtime entertainment personality.

Lee was elected to Stockton’s City Council in November 2024, representing District 6. Mayor Christina Fugazi then appointed him vice mayor in January 2025. But before entering politics, he built his public profile through TV shows like Love & Hip Hop: Hollywood, Wild ‘N Out and Hollywood Unlocked, among others. It gave him exposure to celebrities, and for years, Lee’s been open about sliding into multiple basketball stars’ DMs.

“I used to be infatuated with Kelly; I think I was low-key stalking Kelly,” said Lee to Michael Porter Jr. on Curious Mike. “I remember walking in at a party one day at Fashion Week, and Kelly was there, and I think Kelly saw me stalking him online cause I would post him all the time. I was like, really dead a*s serious. I think I may have even slid into his DMs last time. He never responded. So when I see him, he’s like, ‘Oh shit, bro, let me tell you something, I f*** with you, but I ain’t on that s***. I love you, but not like that. Keep it cool.’

“I was devastated. I thought I had been broken up with in my own delusional mind. I thought I was in a relationship with Kelly, and then he went to have a wife and kids, whatever. And I say that to say I really like how he expresses himself.”

This isn’t the first time Lee has spoken about that night with Oubre Jr. More than two years ago, the media maverick explained what happened and praised Oubre Jr. for being “a good sport” about it.

Lee also told Porter Jr. about being impressed by how some other NBA players carry themselves, even amid social media scrutiny at an all-time high. Jared McCain, an Oklahoma City Thunder star, caught his eye, and Lee even tried reaching out.

“Yeah, I’ve slid in his DM’s too,” Lee said. “He won’t slide back, but I like how he expresses.”

The Thunder guard has developed a reputation for expressing himself through fashion. His painted nails have become one of his most recognizable traits, and he has said he’ll keep embracing that side of his personality.

“I’ve always been comfortable doing it and comfortable in my own skin,” McCain said earlier this year. “I credit my parents and my family for providing me that confidence.”

In 2024, McCain even partnered with Sally Hansen, the brand’s first-ever NIL partnership with a college basketball athlete.

“There’s really no crazy reason to it,” McCain said. “It helps me not bite my nails. “One of the reasons I kept painting my nails is that I had a game after I painted my nails, and I ended up playing really well. I’m not crazy superstitious, but I thought it looked nice, and I thought it helped me play better. So far, it’s worked.

“Sorry if that offends any of you guys. I know a lot of people disagree. A lot of people don’t like it, but I’m just going to be myself and do what I think looks nice.”

A year later, the brand launched a five-shade ‘Most Valuable Polish’ (MVP) collection that McCain helped design. The shades were Bucket Blue, Rookie Red, GOAT Gold, Point Guard Pink and Net Neutral. That willingness to showcase his true personality caught Lee’s attention. This also ties to Kelly Oubre Jr. being his initial interest.

The 30-year-old NBA star’s fashion choices have drawn him heavy scrutiny and allegations that he’s attention-seeking. In fact, Oubre addressed the situation during his time in Washington, saying fans even went so far as to compare his appearance to a woman’s.

“People call me a lesbian a lot,” Oubre Jr. said on the Tipoff podcast. “They think I look like a female girl or a teenage girl or something. I understand I’m a pretty dude. They might be mad that their wife likes me or something.

“I’m not a lesbian. I’m a grown man. I’ve heard that multiple times. I guess it’s something to try to get under my skin, but at the end of the day I know who I am.”

Oubre Jr.’s personal life has also moved well beyond the years when fans were speculating about his dating life. Oubre married Shylynn in 2022, and they have two children: a daughter and a son. That’s primarily why Jason Lee appreciated the NBA star’s polite rejection.

Two months ago on The Truth After Dark, Lee had mentioned a certain NBA player whose DMs he “keeps sliding in” but has not yet received a response. Now it is unclear whether Lee was referring to either Oubre Jr. or McCain, or perhaps a third name. The media mogul also spoke about a lot more than his crushes.

What does Jason Lee think about Enes Kanter Freedom?

Michael Porter Jr. asked Jason Lee about the ongoing WNBA-transgender controversy, which blew up after former NBA stars Enes Kanter Freedom and Royce White declared themselves eligible for next season’s draft.

Last month, Kanter Freedom appeared at a Fever-Sky game wearing a T-shirt that read “WOMAN noun. adult human female” and was ejected for engaging with Natasha Cloud. Security deemed him a potential threat, but Kanter Freedom argued he was only there to support women.

Like many others, Jason Lee also doesn’t align with Kanter Freedom’s purpose.

“I thought he was being a bully,” Lee said. “I thought he was being a b****. I thought it was whack. It was weak,” Lee stated plainly. “What man goes to a WNBA game and heckles and taunts female players? Like, where in your argument of equality or your disagreement with equality or your disagreement with trans being in the sport, when did that become a part of [it]?

“Why are you not advocating for higher pay? Why are you not advocating for better brand deals? Why are you not promoting the sport, since it is starting to finally get a lot more attention than it ever has? You’re just being an as*hole.”

Although the WNBA has deemed both former NBA stars ineligible to play in the women’s league, according to Front Office Sports, the matter is far from over. Kanter Freedom recently sued the Sky, MPEA, and the city of Chicago after being kicked out of Wintrust Arena.