A couple of times Jesse Stone says that he knew he'd get his job back, not getting it back was out of the question as "fate wouldn't do that to me". The same quote is in the first episode of Magnum PI, when Selleck's character (Thomas Magnum) said he knew he'll be able to break into Robyn Masters' Ferrari and therefore get to live in the guest house and use the Ferrari. Not breaking into the Ferrari was out of the question as "fate wouldn't do that to me". Tom Selleck was co-writer of "Benefit of the Doubt" and probably liked that quote from his Magnum character 32 years earlier.
Toward the end of this movie Jesse Stone looks at his wrist watch. It's a close up shot and he's wearing a silver Rolex. The circumference of the watch is half red and half blue, with even numbers displayed 2 through 24. It's the same watch Tom Selleck wore in Magnum P.I. that originally belonged to his characters father. It can be seen in great detail in the fourth season episode "Home from the Sea" and throughout the Magnum seasons.
This is number 8 in the series of made-for-television films featuring Jesse Stone.
David Cristoffel played the character H. Henry Upmann which is also an Old Cuban Cigar Mogul "H. Upmann".