It
is implied that Willie has killed a student at least twice. When a ball
was shredded underneath his tractor, he screams in horror that he ran
over another child again. He claims to be haunted by the ghost of a
deceased student when he confused Bart for him and after Bart left the
scene, a young ghost actually did appear with a rake impaled through its
chest (insinuating murder or at the very least manslaughter). Willie is
homeless and lives in his utility shack on the school grounds which is
heavily dilapidated (on one occasion he dreamt that he was in his shack
when he was actually passed out drunk in a snowy field). His shack has
been destroyed twice (both times because of Bart) when he overflowed it
with creamed corn out of revenge for Willie stealing his skateboard and
the second time was accidentally demolished by a frozen dodge-ball which
was intended at his gym teacher. Despite its shabbiness, Willie is
emotionally attached to his shack as he missed it greatly when he quit
his job and became a waiter, and also was devastated after the first
time Bart destroyed the shack, which partly led to him vowing revenge on
Bart later on.
Willie has a very bizarre way of speaking. His
heavy accent makes most of his sentences sound nonsensical and complete
gibberish. His writing sentences are also heavily accented to match how
he speaks, implying he is also illiterate. Whenever Willie insults
someone he goes into a long-drafted retort that is gruffly spoken such
as "you cheese-eating, surrender monkeys" to a class of French students
and "you nose-combing, hair-wipers" to Skinner and Chalmers. His thick
accent also results in even simple terms being difficult to understand,
as during Nelson's punishment for stealing various items, Willie tried
to tell Nelson to activate a hose, but because of it coming out as
"hoose", Nelson mistook it for "moose." It's implied that Willie's
speech pattern is a result of brain damage due to a constant concussion
by hitting himself on the head with a hammer to get to sleep.
Willie
is a heavy drinker and is usually quite drunk on the job. In these
instances he drives his tractor, swerving drunkenly and ploughing
everything in his way, once crashing into the pool by accident. He
claims to "get so drunk I can barely see, but it helps me get through
another day". Despite this, Willie seems to have a passion for his job
such as keeping the lost retainers that he finds from children and
turning them into a sculpture. Even after Lisa gave him a better life as
a waiter and with a presumably higher pay rise, Willie still missed his
old job as a groundskeeper. Indeed, he often seems to pursue similar
jobs when School is closed and thus his services aren't actually needed
there, as implied by his acting as "Greenskeeper Willie" for the local
golf course, being attached to this job to such an extent that he gets
angered when he receives competition in the form of Bart to the extent
of stealing the latter's pay as revenge.
Willie regularly fights animals such as an Alaskan timber wolf and a donkey, with the intention of eating the latter after holding him down. However, he is quite fond of animals such as giving the timber wolf a drink from his own flask after being victorious, planning to rescue the turtles when the school fire alarm was pulled but was overpowered by them later on, reacting with joy when Santa's Little Helper noticed him through a window and giving a snake a home as a fire hose for the school when he was abandoned by Bart.
Outside of his groundskeeping tendencies, Willie seems to work for Mayor Quimby and the town in general. Presumably due to his constant manual labor Willie is in excellent physique whenever he rips off his clothes and reveals he is actually very muscular which is odd as his clothes tend to give him a pot belly.
He is implied to have an infatuation with Sarah Fergusin, Ducjess of York, as when unknowingly consuming a drink laced with hallucinogenic drug, he proceeded to hallucinate her presence near a tree and her beckoning him to come near her due to his "completing her", with his being all too happy to oblige, even admitting he always dreamed of this moment, also injuring himself due to scratching his face with a rake repeatedly due to mistaking it for her.
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