Ed Dodson has put together an excellent history of the game which eventually became Monopoly, and I commend it to your attention.
I started playing around with some names in Ed's history, and looking to see whether I could find Charles and Esther Jones Darrow in the census or other data at Ancestry.com. I think I found our Esther in the Social Security Death Index:
Name: Esther J. Darrow
Birth: 21 Dec 1897
Death: Feb 1991 - Doylestown, Bucks, Pennsylvania, United States of America
and I find them arriving from Bermuda in 1939 as Charles B. Darrow, born about 1890 and Esther Darrow, born about 1898, with their son William B. Darrow, age 10, born about 1929. Charles was born in Cumberland, MD and Esther and William in Germantown, PA. Their address was shown as 229 W. Hortles Street, Philadelphia.
Searching with that information, I find a genealogy listing Charles Brace Darrow, born August 10, 1889, died August 29, 1967 in Ottsville, PA, son of William Allen Darrow and Isabella Elizabeth Dilley, and married to Esther Edmundson Jones. That genealogy lists William Barclay Darrow as 1929-2006. William A Darrow was born in Maryland to parents born in Massachusetts and Virginia.
Charles Darrow is an only child, according to the Census data. He shows up in the 1900 census on Morris Street in Philadelphia; his father is a civil engineer, and they rent their home. In 1910, same location; his father is a maanager of steam supplies, and he is a salesman of same. In 1920, same location; father is now a district manager, factory supplies, and the son a salesman. They continue to rent. I cannot find Charles and Esther in the 1930 census, but William and "Esabella" still live on Morris Street.
I was curious to see if I could turn up any connection to Clarence Darrow, but did not. Clarence Darrow was born in 1857 in Ohio, to parents born in New York and Connecticut, which makes a connection unlikely, but not out of the question.
I did a bit of searching on Eugene Raiford, and find that he was born in Virginia about 1899. The 1900 Census has him in Georgia, and suggestes he was born there. The 1910 and 1920 Censuses have him in Berlin and Ivor, Southampton County, VA. The 1930 Census has him in Westtown, Chester County, PA. (That's the newest data available; the 1940 Census data will start to be available in April, I understand.) The 1920 census shows the family to include William G. Raiford, age 59; Elizabeth R., age 56, Ellen T., age 26, Eugene R., age 21, Jessie T., age 19, and Edwin W., age 79. Elizabeth was born in Pennsylvania.
The 1930 census, lists Raiford among the residents of the Westtown School Building.
Time doesn't permit me to explore further, but perhaps some other researcher will find this of interest.