LITTLE ROCK, Ark. (KTHV) - Little Rock has an extensive history. After a dead end with Markham, we decided to explore the name behind another historic street: Chester.

In 1820 a well-known attorney named Chester Ashley moved to Little Rock.

Scroll down to take the quiz!

“He was the attorney you would want to have for any squabbles that come up,” said Mike Hood, Little Rock’s Civil Engineering Director.

Land disputes were widespread in the early days and Ashley was the go-to-guy for all things money.

“He was very good at what he did. And he was very savvy at real-estate investment,” Hood said. “Chester Ashley for that time period was probably the wealthiest man in the territory.”

Ashley joined Rosewell Beebe in getting President Van Buren to grant the patent for Little Rock.

“it’s just history. I am just proud that I am a relative,” Roger Cockrill, a direct descendent of Ashley, said. He says his ancestor’s legacy lives on today.

“He donated the cemetery downtown off of Broadway,” he said. “He donated the property of where the Old Statehouse is.”

Money isn’t all Ashley is known for, though, as he left a lasting impact on Arkansas’s legal scene.

“He went into practice of law with Crittenden. They formed the Ashley Crittenden law firm, which later became the Rose Law Firm”

With all of his accomplishments, his career was not unblemished. He was accused of political manipulation and fraudulent land speculation, but historians feel that was a drop in the bucket

“I think being a contributor to the growth of the state and Little Rock in the early days was probably something that qualified to have a street name after him,” historian Mike Polston.

In fact, Ashley doesn’t only have a street dedicated to his first name, but Ashley Street is also named in honor of him.

So far, we’ve covered two streets. One, Markham, which was a little fuzzy and another, Chester, where things are much clearer. Next, we’ll talk about a street named after a man with a questionable history.

Think you have street smarts? Take our quiz on Chester Street here: