In the year 2365, he was involved as a go-between during an internal dispute of the Coalition of Madena, while making an impression on the crew of the Federation Starfleet starship USS Enterprise-D. (TNG episode: "The Outrageous Okona")
He later encountered the crew of the Enterprise again in 2367. After discovering the Erstwhile unmanned but full of precious cargo, the Enterprise crew suspected foul play, given Okona's character, and investigated. They learned that Okona was last registered aboard his ship in the vicinity of Alpha Pintara, unchartered territory light-years away. They followed Okona's trail back to the only habitable planet in the system, reading a single life form on the planet's surface. Receiving a transmission from the surface that needed to be decoded, and unable to reach Okona through shipboard communication systems, Captain Jean-Luc Picard commanded an away team led by Counselor Deanna Troi, comprised of Lieutenant Commander Data, Lieutenant Worf and Doctor Beverly Crusher, in the event that Okona was injured. Transported to the surface, the away team found themselves without their tricorders or phasers, dressed in exotic garb. Okona greeted them, dressed similarly, immediately making a pass at Crusher, although the away team demanded answers of how the freighter captain had ended up in such a strange situation. (TNG comic: "Wayward Son")
Okona explained that after their last encounter he'd been doing odd jobs running food and medical supplies to the planet Jiwan, skillfully eschewing a blockade of Dirolac ships. After this, Okona ended up working for an extremely wealthy and well paying art collector from Beta Athabascar VII, though he grew bored of this. On his last shipment of art objects a couple of months previous he'd been taking a shortcut through uncharted space on his last delivery when he was transported from the bridge of the Erstwhile.
While the planet had appeared unoccupied from orbit, Okona showed Troi, Data, Worf and Crusher an odd, walled stone city with several strange spires, explaining that it was populated with dangerous beings dressed like the away team, which he learned by travelling the streets of the city trying to find answers. Whatever had brought Okona to the city had given him food, a place to sleep and a room full of junk, discarded technology he used to piece together crude communication console. All he lacked was a power source, now provided by Data.
Okona was able to contact the Enterprise, transmitting their coordinates, although Chief Miles O'Brien was unable to transport the team back due to a field of resistance being projected from the city. O'Brien advised the group to get outside of the field, which would allow them to be transported up to the Enterprise. Okona didn't believe they would make it far, but goaded by Worf and a chance for rescue, the group set out into the city. They managed to get farther than Okona had previously, however he was forced to tackle Crusher to save her from an attack from above, as a robed figure on one of the building's rooftops rained down a barrage of flaming, explosive arrows. (TNG comic: "Strangers in Strange Lands!")
Since Troi couldn't read any life or emotions from the archer, the group posited they were dealing with some sort of machine or simulacrum. Under fire from the archer, Worf and Okona allowed the others to draw the enemy's fire while they snuck up and incapacitated the man with strange facial markings. While bragging of their victory over the being, Okona was tossed off the tower, followed by Worf, although Data managed to catch both of them and they proceeded to escape the archer's attention.
They escaped, only to be attacked by an elephant-like monster with multiple trunks and a horn in the middle of its head, ridden by another attacker who lifted Troi in his mount's trunk, swatted away Worf, and then speared Data. While Okona and Data planned a counterstrike, another elephant-monster charged the first, giving the group a distraction they used to escape.
They soon encountered another strange being, a tall, muscular, green-skinned, blonde alien woman in strange armor who seized Okona and pulled him into a passionate kiss. Troi teased that she never thought she'd see Okona daunted by a woman, and Crusher added that if he weren't so charming he wouldn't have that problem. The alien woman led them through the city streets, eventually taking them underground and outside of the city. Meanwhile on the bridge of the Enterprise, Ensign Tess Allenby finished decoding the message and learned that the civilization build expansive burial monuments for their leaders and filled them with holographic recreations of their friends, family and enemies, then brought passersby down to the planet to show them the lives and perspectives of great rulers.
Now outside of the city and able to communicate with the Enterprise, Picard explained what had happened. Okona apologized for his distrust of the alien woman, a simulated representation of the queen or mate of the the king for whom the tomb was constructed. After bowing to her, which seemed to please the being, Okona and the away team were transported back to the Enterprise. (TNG comic: "City Life")
After the events of the burial monument, Okona briefly accompanied the crew of the Enterprise as they surveyed a pulsar designated as Beta Caligula. He chatted with Data about Crusher, eventually realizing that she was the mother of his friend, Wesley Crusher. He decided to give up chasing after the doctor, as he had a rule of not getting romantically involved with his friends' relatives, something he thought was reserved for his friends' sister until then. While the Enterprise surveyed Beta Caligula, Okona was unknowlingly frozen by the entity of pure life-essence that had singled out Worf's memories and impersonated K'Ehleyr. (TNG comic: "The Remembered One")
- TNG episode: "The Outrageous Okona"
- TNG comic: "Wayward Son"
- TNG comic: "Strangers in Strange Lands!"
- TNG comic: "City Life"
- TNG comic: "The Remembered One"