Why does Dill's explanation of Jem's state of dress almost land him in trouble?

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In Chapter 6, the children go on a nighttime raid into the Radley yard to peep through the windows in hopes of getting a look at Boo. However, Nathan Radley hears the children and ends up shooting his shotgun in the direction of the intruders. During their escape, Jem's pants get caught in the Radleys' fence, and he is forced to take them off. After the children run to safety, they decide to walk down to the front of the Radley yard where their neighbors are gathered; the children want to avoid suspicion. When Atticus sees that Jem is not wearing any pants, Atticus asks Jem what happened to his pants. Dill, who is always quick to come up with a story, tells Atticus that he won them playing strip poker. Miss Rachel gets upset at Dill after hearing that the children were gambling, and Jem lies by telling his father that they were only playing with matches. Dill's explanation almost gets him into trouble because his aunt and the other adults do not allow the children to gamble. 

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When Jem loses his pants in the Radley's fence in Chapter Six of Harper Lee's To Kill a Mockingbird, Dill comes to the rescue with a quick explanation. Jem had approached the Radley's back porch in hopes of getting a peek at Boo, but a shadow frightened him and all three kids ran for safety. While crawling through the fence, Jem became entangled and abandoned his pants. When the kids joined the group of neighbors who had gathered after hearing Mr. Radley's warning shotgun blast, Miss Stephanie and Atticus noticed that Jem was in his underwear. It was Dill who interrupted to explain that Jem had lost them "playin' strip poker up yonder by the fishpool." To Miss Rachel, Dill's aunt, this was probably worse than the truth.

"Gamblin' by my fishpool? I'll strip-poker you, sir!"

As Scout pointed out, "Matches were dangerous, but cards were fatal."

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I think you’re talking about the episode where Jem sneaks into the Radley yard and tries to peek through the back porch window to see if he can see Boo.  Jem gets scared when he sees a shadow pass along the wall of the house and runs away, only to get his pants caught on the Radley fence.  In an attempt to get away, he takes off his ripped pants and leaves them there.  When Nathan Radley (the scary shadow Jem sees), shoots his shotgun in the air as a warning for the intruder, everyone in the neighborhood comes out to see what is going on.  That is when Atticus catches Jem without pants.  When Atticus asks Jem where his pants are, Dill tells Atticus that Jem lost them playing strip poker.   Not only does Dill lie, but playing strip poker is not a proper thing for children to do.  Luckily, the excitement of the shotgun blast distracts Atticus away from further cross-examination of the half-naked Jem.  Jem and Dill go to bed, and Jem sneaks out to go get his pants, and he finds them mended laying over the Radley fence.

Dill, a master at making up stories and lies, could have gotten in trouble for lying and for playing the “adult” game of strip poker as well.  Atticus, however, put two and two together and figured out what Jem and Dill had been up to.  Luckily for Dill, Atticus didn't make a big deal out of it.  He probably felt that Jem and Dill learned their lesson by being scared and almost getting caught trespassing on Radley property. 

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