[2] Cullen grew up in San Antonio with his mother and siblings; his father had abandoned the family when Roy was only four years old.

A misguided kidnapping attempt by his father a couple of years later brought Roy closer to his mother, who was shaken by the event.

Roy lived out his childhood in poverty, even resorting to dropping out of school in the fifth grade to work at a candy factory to help his mother pay the bills.

[3] Still seeking a path in life, Roy moved with his half-sister and her husband to Schulenburg, Texas, where he found a job in a cotton-trading office.

After marrying Lillie Cranz, his girlfriend of five years, he continued working as an independent cotton broker, but he searched for a new venture after he lost his savings in the Panic of 1907.

Roy worked for and traveled with Cheek for the next five years, buying leases on land in Central and West Texas, 43 in total.

Roy knew of one that he felt was promising, and it lay in the old Pierce Junction oil field inside the Houston city limits.

He wouldn't drill near the center as the previous drillers had, however; Roy had a hunch that the outskirts of the salt dome, where it dipped in the ground, was where oil could be found.

He would drill deeper into the ground, despite technical issues and the higher cost, in order to reach the large oil deposits.

The investors took the chance, and the result was the second Pierce Junction gusher, giving Roy his confidence again and establishing him as a respectable oilman.

Roy had similar fortunes drilling the perimeter of the old Humble Field, championing a troublesome layer of shale rock 3,500 feet below the surface, eventually reaching oil-rich Yegua sand.

This was in response to a group of zoning advocates led by Jesse H. Jones, financier and owner of the Houston Chronicle.

It funded the expansion and renovation of what became known as the Hugh Roy and Lillie Cullen Building of Southwestern University in Georgetown, Texas.