"The Territory" by Bradley Denton

First appeared in Fantasy and Science Fiction.  Reprinted in major genre retrospectives by Brad Templeton, Gardner Dozois, and Gordon Van Gelder.  Up for Hugo, Nebula, World Fantasy, and Locus awards.

After his brother dies, Samuel Clemens signs up with a Missouri Confederate group to get revenge.  Clemens can't shoot, ride or do anything very well, but he joins.  The threat of calling him a Yankee spy seems ever present.  He and two others are sent to Lawrence, Kansas--a stronghold for the abolitionists who have stolen "property" [i.e. slaves and real objects].  They find out that the town has no suspicion that they might come under attack.

Meanwhile, Henry, a boy Clemens ran into at the newspaper, dogs Clemens' footsteps much to Clemens' annoyance. Clemens taps his cigar ash on the boy's head to be rid of him, but he does need the boy later.

Clemens dreams of future events and knows when people will die.  He dreams of the boy's death which haunts him.  He expects the boy to blame Clemens for his death.  Worse, the Confederates are needlessly cruel and kill men uninvolved in the war if they don't aid the Confederates' cause.  Clemens has a change of heart but cannot escape, lest they shoot him down--him inferior to the Confederates in every way... except in lying.

The humor seems more W.C. Fields' than Samuel Clemens, but the interaction between the boy and Clemens is classic--worth studying--not to mention vital for establishing Clemens' motive for a change in heart.  Well played.

The boy has a number of annoying features, and we feel some tension when the questions dig toward Clemens' motive for being in the town.  Denton brilliantly walks a fine line between showing innocence and deviousness masquerading as innocence.  Does the boy suspect or no?  Which makes him all the more annoying, necessitating Clemens' brushing the kid off without offending but eventually Clemens does the cigar, which is cruel and something most folks wouldn't do, but he's pressured to act.

While he succeeds in brushing off the boy, Clemens discovers he needs the boy's timepiece in order to finish his reconnaissance.  A cigar as payment is arranged.  Neither likes the other.

One of the better extended scenes in the genre.  Beautiful tension.  Without this scene, there'd be less sympathy for the boy's possible demise.