In what way is the escape of Huck from his father and Jim from slavery similarly ironic to Tom's elaborate release of Jim from his imprisonment in The Adventures of Huckleberry Finn?  

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The other irony in this comparison is that Tom’s elaborate schemes for Jim’s escape are not actually very clever.

Huck’s escape from his father’s cabin is ingenious because the young boy comes up with an elaborate ruse to fake his own death. Not only does he procure convincing blood to indicate his death, he axes the front door and removes all his valuables to stage a robbery-homicide. Huck’s actions are clever because they convince both Pap and the entire town that he is deceased.

On the other hand, Tom’s ideas to bust out Jim from Aunt Sally’s are ridiculous and unnecessary. Instead of merely lifting the bed to which Jim is chained, Tom suggests they saw off the leg of the bed or even Jim’s foot. This shows Tom’s juvenile understanding of escape and his need for things to feel dangerous. Huck’s escape plan was actually dangerous; if Pap had caught him, Huck surely would have suffered physical abuse. In this case, Tom’s escape plan is elaborate in ways it doesn’t have to be because there are no real stakes for him.

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The reason the resemblance is ironic considering these two escape plans is that the elaborate nature of Huck's escape was necessary and the elaborate nature of Jim's escape was not. 

Huck had to plan carefully so that he could 1) escape from his father and 2) convey the idea that he has been killed. Huck does not only intend to escape, but to fool his father (and the town) into thinking he is dead. For this reason, Huck has to concoct an elaborate plan, complete with detailed "indications" of murder. 

Jim, conversely, only needs to escape. The elaborate plans that Tom makes to help Jim escape do not actually help but only add "adventure" to Jim's liberation. 

The irony rests in this discrepancy. We read Huck's escape plan as something of necessary genius and the plan for Jim's escape as genius applied groundlessly.

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