Please discuss the ways in which Irving manipulates our sympathies in his story "The Legend of Sleepy Hollow"€”which varies from ridicule of Ichabod...

To be
perfectly clear, Irving never offers an affectionate picture of Ichabod Crane, but it is true
that the point of view shifts more to Crane's eyes as the story progresses, and we gain a bit of
sympathy (pity would be a more accurate term) for him as he goes up against Brom
Bones.

Crane is far more anti-hero than hero throughout the story. He is an
underhanded and two-faced person. He beats the children viciously in his role of schoolmaster
but shows a different face to the mothers: he is gentle, ingratiating, and kind around them. He
courts Katrina and wants to marry her but only because he covets the wealthmost particularly the
foodher father's farm offers.

Although he is very thin, he is a glutton.
Although he is the supposedly learned schoolmaster, he is ignorantly superstitious and believes
in witches and ghosts. He is portrayed repeatedly as a person out for himself. He is cruel to
those under his power but servile to those with power over him. He licks the boots of the
powerful and kicks with his own boots the powerless. We would fear for Katrina if he married
her, because we know his servile courtship would turn into disregard of her feelings or needs
once he had her farm and money.

Yet the narrator treats him with satiric
humor rather than open condemnation, and Crane does work hard between the school, his singing
lessons, and the help he provides:

He assisted the farmers
occasionally in the lighter labors of their farms; helped to make hay; mended the fences; took
the horses to water; drove the cows from pasture; and cut wood for the winter fire.

In addition, after he is competing with Brom Bones for Katrina, we
do feel some sympathy for Crane. For instance, Brom and his gang vandalize his singing school
and schoolhouse. The description of that raises some sympathy (or pity) in us for what Crane is
up against:

They harried his hitherto peaceful domains;
smoked out his singing-school, by stopping up the chimney; broke into the school-house at night,
in spite of its formidable fastenings of withe and window-stakes, and turned every thing
topsy-turvy: so that the poor schoolmaster began to think all the witches in the country held
their meetings there.

We hear, too, that Crane's marriage
proposal to Katrina is met with rejection:

Something,
however, I fear me, must have gone wrong, for he certainly sallied forth, after no very great
interval, with an air quite desolate and chop-fallen.

We
can feel some sympathy for Crane being so thoroughly bested by Brom, but Crane is a difficult
character to like.