RBP has said Selleck's portrayal of Jesse Stone is 'dead on'.

"He ain't no small-town shit-kicker," Hawk said.
"I know."
- Spenser and Hawk after meeting Jesse Stone in Back Story

In 1997 Robert Parker introduced the world to Jesse Stone, who comes to the small town of Paradise to serve as police chief, running from a past in Los Angeles where his alcoholism led to a failed marriage and a failed career in law enforcement.

Jesse was a talented minor-league baseball player permanently sidelined by a shoulder injury. His missed opportunity at a career in the pros is one of the many regrets he comes to deal with.

Laconic, pragmatic, and world-weary in a way that few in the wealthy town of Paradise understand, Jesse succeeds in dealing with criminals who would normally overwhelm or outmaneuver a typical small-town force.

He shares Spenser's world, making a brief cameo in Back Story and encountering several of the same characters. In particular, Jesse becomes friends with State Police Captain Healy to an extent Spenser never manages, and even dates Rita Fiore at one point (which is also something Spenser never does). Jesse also develops a rapport with Boston mobster Gino Fish.

Jesse Stone is basically a younger, alternative version of Spenser. As the author said in an interview,

"I wanted to do a third-person [narrative]. I wanted to do it with somebody who was not as evolved as Spenser was. So, I got Jesse at thirty-five with a drinking problem and a marriage that had gone on the rocks."

He essentially shares the same core character traits as Spenser. Both started a pro athletic career, but while Spenser made a conscious decision to walk away, Jesse was forced out by injury. Jesse's drinking got the better of him, while Spenser managed to get it under control before it became an insurmountable problem. Both have autonomy and intimacy issues which impede participation in a conventional married relationship; Spenser and Susan navigate to a workable solution, while Jesse and Jenn do not. Jesse's better able to function in an organizational structure - somewhat - which is why he's still a policeman and Spenser's on his own.

The Jesse Stone books have all been adapted into TV movies which are generally much better than any of the Spenser screen adaptations. Tom Selleck, despite being five inches taller and twenty-five years older than the young "middleweight athlete" Jesse is in the books, embodies Jesse's laconic, troubled, world-weary persona so well that the differences don't matter.

RBP must have found Jesse to be a more interesting character to write than Sunny Randall, because eventually Sunny's series ends and she appears as a character in Jesse's, providing a romantic interest who can possibly match him issue for issue.

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