Sleepy Hollow (1999)
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She used the Horseman to kill every person who was an obstacle between her and the Van Garret's legacy: She had old man van Garrett killed for his money and possessions, but also out of revenge, because he had forced her family out of their house when she was young. Widow Winship and her unborn child were killed because the child was van Garrett's. Van Garrett had changed his will to make his unborn child the beneficiary of his inheritance. This new will disappeared with van Garrett's death, so van Garrett's son from an earlier marriage remained his heir. When Van Garrett's son was killed, this made Baltus van Tessel the next in line to receive van Garrett's legacy. So he was beheaded too. This made Katrina van Tassel next in line, so she was the next target. Had the Horseman succeeded, then Lady van Tassel would have been the final beneficiary of the legacy, being Baltus van Tassel's wife. Everyone who had any knowledge of the unborn child and van Garrett's changed will was a possible liability, and had to disappear too. Jonathan Masbath had to die because he signed the new will as witness. Magistrate Philipse had to be killed because he had helped widow Winship with the legal issues concerning her child and its rights. Midwife Killian and her family were killed because they knew that widow Winship was pregnant with van Garrett's child. The other people who knew about the child or the will were silenced in other ways. Notary Hardenbrook was too scared to talk and hanged himself; Reverend Steenwyck was kept silent because Lady van Tassel had seductive power over him; and Doctor Lancaster was blackmailed by Lady van tassel because he had fornicated with the housemaid. Edit (Coming Soon)
Why would Katrina van Tassel would want to keep the magistrate, doctor and others happy in fear, blackmail, lust or other way so that they keep their mouth shut since they knew of the new Will and the Widow's unborn child? She already took care of the next legal heir to Garrett's wealth by killing them, she didn't really need magistrate, or doctor etc in her side. What possibly would have happened if they were not in her pockets?