Whenever DeMar DeRozan hits the trade block, the whispers follow. Speculation snowballs—rifts with teammates, friction with the front office, or locker room drama. It’s become a pattern. The same thing happened when he was traded from Toronto to San Antonio. Back then, it felt like he was destined to retire a Raptor—until Kawhi Leonard became available. Now, after a whirlwind few months in Sacramento, DeRozan’s name is back in the rumor mill. But this time, a close friend and former teammate is pushing back on the narrative.

On 7PM in Brooklyn, DeRozan reunited with Rudy Gay—their third time as teammates after stints in Toronto and San Antonio. Their on-court connection has always been strong, but their off-court bond might be even tighter. Back in the Spurs days, the spotlight was relentless. Whether it was Gay tossing DeRozan’s shoe mid-game or the subtle ways Deebo leveled up with veteran help, every moment was dissected. Even their jokes were sometimes mistaken for tension.

However, DeRozan states, “I ain’t gonna lie, one of the one of the best times in in in my career after that situation happened was to go to uh San Antonio and play with him,” he refers to Rudy Gay. Rudy claims that Deebo saved him at that time of his career and the latter revealed that Rudy helped him get over the shock of the trade. As DeRozan joked, “Cause he [Rudy] really a negative person, like one of my most negative friends.” 

The negative friend went to bat for him against Drake and his diss. However, that time their banter, friendly trash talk, or even moments of silence were misunderstood. “it would look like we were being disrespectful to each other,” Rudy said.”I remember sitting in practice one time and like they just looking at us like, ‘Are they about to fight?’ Like, ‘No, that’s how we talk.'”

Apart from having that banter, Gay reveals what kind of friendship they still have. “The thing about it is we wouldn’t allow nobody else to talk to each other talk to us like that. You know what I mean? That’s real friendship right there.”

DeRozan agreed. At this moment in time, he really needs a friend like Rudy Gay to vouch that he’s a reliable presence in the locker room.

DeMar DeRozan is the veteran this time

Perhaps it’s how they reunited that set the tone for DeMar DeRozan and Rudy Gay in San Antonio. When DeRozan found out he was traded, Gay was his second phonecall. His vet pretty much laughed in his ear at how angry Deebo was. Gay calmed him down and helped his transition from Toronto to San Antonio.

Both were shipped to different destinations in 2021. Gay retired in 2024 and Deebo landed with the Sacramento Kings at that time. But this might not be the long term plan.

He had an altercation at a sushi bar in Sacramento in April but that was soon forgotten. DeMar DeRozan has emerged as one of the top trade targets this offseason with multiple teams reportedly interested. The wing could reportedly be part of a blockbuster multi-team trade. The likelihood of staying with the Kings has a slim chance. And apparently, the Bulls are out of contention because he just listed his former Chicago home for $6.25 million this week.

Whatever trade snags Deebo, Rudy Gay might be the first call. Hopefully he won’t laugh this time.