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Jesse as a live-action 14-year-old teenager in the second film and a long-lost cousin of Christopher Robin.

Jesse Greenwood (played by Jason James Richter in the first three films and voiced by Zachary Bennett in the animated series) is the main protagonist of the Free Willy Series. In the first film, this twelve-year-old street boy has not seen his real mother (who is mentioned to be dead in the second film) in a long time and spends his days stealing from people and living on the streets, much like Aladdin.

That is, until he befriends Willy, a lonely orca, while doing community service at a local aquarium, befriending a shaman named Randolph Johnson, and finding new parents, which happen to be his adoptive parents Glen and Annie Greenwood.

Eventually, he rescues Willy and returns him to the wild after learning that his keepers want him dead to collect insurance money, keeping him out of the reach of an evil man named Dial.

In a TV series, Jesse and Willy go on exciting adventures under the sea.

In the second film, Free Willy 2: The Adventure Home, Jesse, with his half-brother, Elvis, and his first ever girlfriend, Nadine (goddaughter of Randolph), reunites with Willy and together they successfully battle a burning oil spill to ensure Willy's escape to the open ocean with his sister, Luna, and his younger brother, Little Spot.

In the third film, Free Willy 3: The Rescue, Jesse is now a secondary character, and he, along with his old Native American friend, Randolph, and a shy new friend Max Wesley, try to foil Max's father's illegal whaling operation to preserve the birth of Willy's and mate, Nikki's, son.