In A Long Way from Chicago, what grade did Grandma say that 16-year old Ernie Cowgill was in?
Grandma says that sixteen-year old Ernie Cowgill is still in the fourth grade.
Grandma has a propensity to exaggerate, so whether the hapless Ernie Cowgill is really still in the fourth grade or not is unclear. Whatever the case, it is quite evident that Ernie is not very bright. The Cowgills are the owners of a dairy farm, and the boys deliver milk and eggs to their customers in a horse-drawn milk wagon. There are four Cowgill boys - the older three, according to Grandma, are "big bruisers". Ernie is the youngest of the brothers, and is described as "a big, tall galoot of a kid with narrow eyes". Grandma says he is "the runt of the...litter".
The Cowgills are notorious for perpetrating destructive and annoying pranks in the town. It is they who are identified as the likely culprits when Grandma's mailbox is "blown...sky high", and when Mrs. Wilcox's privy is overturned and destroyed. Seeking to get back at the troublemakers and put them in their place, Grandma concocts an elaborate plan to beat them at their own game. She lets it be known that no one will be home one night, then lies in wait while, as expected, the Cowgill boys come breaking in with the intent of "pilfering" and doing other mischief. Grandma stuns the would-be vandals with a cherry bomb, then holds the boys at gunpoint while Joey runs to the church to fetch their parents. When Mr. and Mrs. Cowgill arrive, Grandma turns the boys over to them, but only after Mr. Cowgill has enacted "justice", "whal(ing) the tar" out of each of them with Grandma's long leather strop (Chapter 2 - "A Mouse in the Milk").