When it snows in Alameda—or more properly when we think about snow in Alameda—there are a few things that come to mind: When did we last fill the oil tank? Will the kids get a day off? Where did we put the sleds?

Which leads to the next thought: Deadman’s Hill.

Over the years we’ve sledded down, walked up and often wondered about the namesake Dead Man behind the slang name for Stuart Drive. In this case, it’s not just a myth, it’s a real story about a well-known and popular Portland businessman who died in 1917 in a freak accident that rattled the business community and shocked the young Alameda Park neighborhood.

Fred A. Jacobs, art collector, civic booster, real estate broker and owner of the Fred A. Jacobs Company, had set out with his employee J.P. Parker to drive through Alameda on their way to have a look at rental properties in the Vernon neighborhood. At the time—and well up until the 1970s, we’ve been told—Stuart Drive was a two-way street. On the morning of June 5, 1917, they started up Stuart Drive on their route north. Why they chose Stuart Drive over the gentler and wider Regents Drive is anyone’s guess. The car made it about half way up the hill, but then stalled out and started to roll backwards down the street. Unfortunately for Parker and Jacobs, the emergency brake did not hold and the car rolled to the far left side of the street, went backwards over the curb, bumped over the small sliver of property that goes with the lovely George A. Eastman-designed Craftsman home there on the hill, and then flipped over hard, landing on its side 25 feet below on Ridgewood Drive. Here’s what The Oregonian said the next morning:

From The Oregonian, June 6, 1917

Jacobs, age 47, left behind his wife Gussie and two children, Elizabeth, and Fred Jr. Pallbearers for the funeral—held with full Masonic rite honors—included Portland’s most powerful and successful business leaders. Services were held at home, and then again at graveside. No known plaque or marker was ever put in place in honor of Fred Jacobs. The real estate company bearing his name lived on for many years. Jacobs was responsible for platting and then selling multiple chunks of farm and forest that are now integral parts of the neighborhood, including the Manitou Addition.

The same story that carried news of the fatal accident also described the hill as a perilous spot and the scene of other accidents. Indeed, an earlier news story, this one from April 19, 1912, described a serious but non-fatal collision between a motorcycle and a car near the top of the hill that ended up with the car over the side and smashed into a just-finished (and now much remodeled) house, and motorcycle driver and passenger pinned under the car.

Here’s The Oregonian’s description from April 19, 1912, and even a photo.

From The Oregonian, April 19, 1912. Click to enlarge.

Here’s some bonus information that we found fascinating: A later news story about the motorcycle vs. car accident, and the law suit that resulted, appearing on July 3, 1914, helps solve another mystery about the hill. Frequent readers of the blog will recall the post about “Hugby” Drive, which we now know was Rugby Drive. The July 1914 story refers to the accident as happening at Rugby Drive and Alameda Street. A search through the city’s street naming records shows the only “official” Rugby Drive as being on the Westside. References to Stuart Drive exist both before 1912 (including in the original 1909 plat) and long after, so we’ll have to continue wondering about the story behind this visible but extinct street name. Theory: the Alameda Land Company boys had it set in the concrete curb before the official naming protocol became clear.

One more item, for the record: the late Portland historian Eugene Snyder, author of the definitive Portland Names and Neighborhoods: Their Historic Origins, which we greatly admire, guesses incorrectly about who Stuart was. After researching E.Z. Ferguson, president of the Alameda Land Company, and understanding more about his social network, it’s clear to us that Stuart was Donald M. Stuart, Ferguson’s business partner, owner of the Spencer-McCain-built home on the northwest corner of 26^th and Hamblet, (less than a block from Ferguson’s Craftsman mansion at the southeast corner of 26th and The Alameda). Long-time friends from Astoria, Stuart served as pallbearer at Ferguson’s funeral in July 1917.

Sled carefully please.