Star Trek: Strange New Worlds co-showrunner Henry Alonso Myers teases Lt. James T. Kirk (Paul Wesley) reuniting with his older brother, Lt. George Samuel Kirk (Dan Jeannotte) in season 2. Paul Wesley returns as Kirk in Strange New Worlds season 2, episode 3, "Tomorrow and Tomorrow and Tomorrow." However, there may be time travel shenanigans involved because it appears to be a version of Captain Kirk who meets Lt. La'an Noonien-Singh (Christina Chong) in the episode instead of the younger Lt. Kirk who serves on the USS Farragut in Strange New Worlds' 2259 timeframe.
In an interview with StarTrek.com, showrunners Henry Alonso Myers and Akiva Goldsman were asked about the chances of James and Sam Kirk seeing each other when Jim comes aboard the USS Enterprise in Star Trek: Strange New Worlds season 2. Myers confirms it will happen, and hints at the dynamic between the Kirk brothers. Read his quote below:
“We do see them. We seem them together. That sort of touches on the fundamental thing of what we are trying to do when we’re using elements from the past… We never knew anything more about them except some brief things, in some of the books. We wanted to take a moment, ‘Okay, he’s got a brother. What’s their relationship? Why is their relationship like this? What’s it like to be connected to the two of them?’… When Akiva wrote the pilot, he put in this [Sam] Kirk thing and tossed it in the air saying, ‘Okay catch. Anyone who wants to catch it, catch it,’ That’s what it was; to find moments for them, deepen it, understand what this relationship means. It wasn’t a concern for The Original Series, but how cool is The Original Series now that you know there is actually depth to their relationship?”