
Although I never had the privilege of knowing my great grandfather, I feel as though the last few weeks I’ve spent researching his life and work have taught me a lot about him. I know there are still volumes to learn, but, for now, the time has come to close his chapter and move on to the next. So, in my own style, I’ve decided to eulogize him here. I’ll probably always refer to “the picture” as the “Hot Great Grandpa Photo,” but now at least everyone knows who I’m talking about. And having learned so much about his personality, I think he might actually be having a little chuckle out of it. So without further ado, let’s all raise a glass, not shed a tear, and remember that he had fun and enjoyed living.

From even the earliest days of his childhood, William Stewart Dinwiddie always did exactly what he wanted. His obstinate side landed him in boarding school, his mother thinking the right approach might lead him to academic success. It was quickly confirmed by the schoolmaster that this wickedly handsome and funny country boy could be “neither led nor driven,” and for anyone less resourceful, this might have been the end. Rather, it was just the beginning. By the time he left military school for his first job in Chicago, he had his mind set on success.


His timing was perfect. 1890s Chicago was fertile ground for skyscraper builders. Though his brother got him his foot in the door, it was up to him to stay in the room—a room filled with giants—pioneers. The brothers and their peers learned their trade from the floating foundation up. Their mentors were the likes of Burnham, Root, and Wright, and they got their education straight from the source. Some of his peers would soon become family, and the bonds they formed would last a lifetime. They worked late nights and spent their lunches carefully observing skyscraper construction teams. They were sponges, soaking up everything they could.
But it wasn’t ALL work. This handsome and charming gentleman swept his peers’ sister off her feet and married her—then carried her off to Louisiana for a brief stint with the Army Corps of Engineers, drafting on a set of locks that would open further trade with the Mississippi. Although bayou living blessed the newlyweds with two sons, drafting the lock was frustrating by all accounts—even the Corps’ own archives. So it’s not surprising that when the in-laws called with a job offer back in Chicago, the growing family beat feet back to the Windy City.


His first job back in the city with his in-laws was a home run, and he was so successful and well liked that soon, he was managing the Chicago operation. He made crazy deals and jaw dropping promises. To him, a handshake and his word were as solid as any of his structures. But he always delivered. He knew his business inside and out. He met challenges head on, he trusted his employees and empowered them. He respected the men who worked for him, and in return, they respected him—so much so that nearly every single contract he entered into was delivered early and under budget. He set records and he broke them. Routinely. In a meeting that would set the trajectory for the rest of his career, he pointed his bat to the horizon, swung with all his might, and hit the ball into the stratosphere.

When the first “big one” and the fires that followed prompted massive reconstruction on the Pacific coast, the family was happy to make the journey out west. Having had a rural upbringing, he missed the outdoors, and California held the promise of the nature-filled days of his youth. He rose to the challenge of reconstructing a better, safer Pacific Coast. As the head of the west coast operation, again, he made history over and over again.

When opportunity presented itself, he took a leap of faith and again came out on top. Through hard work and determination, he fulfilled the ultimate American Dream and started his own business. With an initial intent to keep things small and manageable, his reputation preceded him, and before long, his fingerprints were all up and down the Pacific Coast. From the historic buildings of Oregon to the skies of California, the his name came to be synonymous with height and strength and efficiency and durability and speed and beauty. Over a century later—monuments greater and more awe-inspiring than anything in any cemetery or graveyard stand as a testament to his dedication and attention to detail.

His legacy in steel and masonry is well documented, though somewhat difficult to unearth—a fact I am determined to change. But his legacy in flesh and bone is more enduring. Together with his beautiful, smart—and strong wife, he built a family. Both he and this amazing woman gave the world five sons who would each go on to make their own marks in the world. In his own way, each son forged his own path. These five sons each brought forth two grandchildren, some of whom he was fortunate enough to have known. And from these ten grandchildren, new generations have come forth—and personally, I hope they realize what a fine man this William Stewart Dinwiddie was.

From his childhood in rural post Civil War Tennessee and Virginia to the tops of the clouds in Oregon and California, my great grandfather did something we can all only dream of doing—he stuck to his guns. That schoolmaster was right—he could NOT be LED. He could NOT be DRIVEN. Because he wasn’t destined to be a follower or a passenger. William Stewart Dinwiddie was a LEADER. He was meant to DRIVE. And he knew it from the beginning. It just took awhile for everyone else to catch up.
Here’s to you, Great-Grandpa Bill. You may be gone, but you are most definitely not forgotten.
Thank you for your posting of the life of William Stewart Dinwiddie. I had wondered why Helen’s mother Helen Ekin died in Oregon. At first I thought that it was because Oregon had been one of the first states to grant women the right to vote so she relocated from Chicago to Oregon. Now I know that it was because her grandchildren were living in Portland, Oregon. In fact she was living in their home, or her home (?). A great series! I look forward to future installments.
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Actually, Bill, she moved out there, and then both girls moved to Berkeley! I am working on Helen Ekin now, so I will be definitely contacting you. I have some questions. I’m not sure where she is buried…. Do you know?
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Oh, and I think it was her home, but on the same street as Bill & Helen. I think the boys built her a house and gave it to her. Still digging up the details.
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I rechecked the records and you are correct in that they are both living in Portland, OR. on Sherwood Drive. Helen at #730 and the Dinwiddie family at #637
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