Offbeat Oregon History

If you ask most Oregonians who the first woman governor in state history was, they’ll have an immediate answer … but they’ll be wrong.

Conventional wisdom holds that the first woman to take the gubernatorial purple in the Beaver State was Barbara Roberts, who was elected to the job in 1990. In fact, that’s almost true … but, of course, “almost” doesn’t work very well as an answer to a true-or-false question.

The truth is, Barbara Roberts was the first elected woman governor in Oregon history. But the first woman to serve as governor of Oregon — or any other state, for that matter — was a remarkable woman named Caralyn B. Shelton.

It was because of Caralyn Shelton that Oregon, for one historic weekend in early 1909, became the first and only state in the nation with a female governor. This was especially ironic because it wasn’t until 1912 that women won the right to vote in Oregon.

Caralyn Shelton was born in 1876 to Willis and Mary Skiff, prominent members of the business community in the town of Union. Willis was the town’s Justice of the Peace. By all signs Caralyn’s early childhood was a happy one; but it was derailed by an unknown hand on the night of July 24, 1886, when Willis Skiff disappeared from a deserted railroad platform as he waited for a midnight train. Foul play was strongly suspected, and Pinkerton detectives scoured the scene looking for some sign of his body; but none was ever found. The case is still unsolved to this day.

Two years later the other shoe dropped. Following a short illness, Mary Skiff died in 1888, leaving Caralyn and her two siblings, Nolan and Mabel, as orphans.

So the three children were more or less adopted by Judge John W. Shelton, an attorney, and president of the Union Railway, who had handled Willis Skiff’s estate after his death. Shelton and his wife, Mary, had been unable to have children, so having a “ready-made family” come and fill their empty nest worked out nicely for everyone involved — or so it seemed.

But Judge Shelton seems to have been a pretty serious rascal, to put it mildly, because a couple of years later, while Mary was on an extended visit to her family back home in California, he apparently got some friends to publish rumors about her engaging in lewd and promiscuous behavior. (This was, of course, back in the day when one needed a good reason to get a divorce.) The instant these reports were out, Shelton, citing these false published claims (which none of my sources were indelicate enough to get specific about), sued for and got a quick divorce from Mary … and then turned around and married his young ward, Caralyn. The two of them actually eloped, if that’s an appropriate word, across the state line to Weiser, Idaho, to tie the knot.

Mary Shelton returned home to find herself divorced and penniless, and with all of Union County atwitter about whatever nasty and slutty things old man Shelton’s friends had claimed she did.

Well, the 1800s was a time when older men commonly married young women; but they were not usually that old, or that young. Shelton was well past his mid-40s; Caralyn had just turned 16 a few days before. Moreover, she was Shelton’s stepdaughter. She’d been living in his house since she was 12 years old and she’d looked upon him as a father figure. Had he taken advantage of that relationship to initiate a statutory-rape relationship with her before divorcing his wife? Well, yeah, of course, he had. Had that been the real reason he wanted to divorce Mary? We don’t know, and neither did all the neighbors, but that wasn’t (and isn’t) stopping any of us from speculating about it.

Certainly, that is exactly the conclusion Mary Shelton drew from this chain of events, and she immediately got an attorney and set about suing Shelton’s big-mouthed friends for $50,000 for libel, and Shelton himself to have the divorce overturned.

Well, to make a long story short, that happened. In 1894, Mary Shelton got a court of law to overturn her divorce and thereby annul young Caralyn’s marriage. By this time, though, John Shelton had actually died, so the fight was no longer over the man, but over his estate.

Out of that fight Mary emerged victorious, so she inherited Shelton’s estate, and Caralyn, her reputation hopelessly sullied in Union through no fault of her own (I mean, come on, she was a child when all this happened), decided to stay in Portland — where she and her ersatz husband had moved shortly after their marriage.

Needing a job, she took one as a stenographer for a young attorney named George Chamberlain.

(A quick side note: Mary Shelton subsequently sued for and was granted reinstatement of the divorce from her by-now-long-dead husband. Historian Richard Roth suggests she probably did so to avoid being held liable for his business debts.)

Over the following few years as the newly “unwidowed” Caralyn settled into her work, her new boss, George Chamberlain, noticed his young typist’s aptitude for the law, which she had probably cultivated during the year or two when she’d been married to John Shelton. Shelton, who’d had to start up a new law practice in Portland after slinking out of Union with his new child-wife, no doubt had pressed her into service as an unpaid legal assistant while he was working to build up his business. If so, the skills she learned served her well in her new job. (But we’ll probably never know, because in the few interviews she did over the years for newspaper stories, she never said a word about old man Shelton, giving all credit for her legal training to Chamberlain.)

Soon Chamberlain had Caralyn functioning more or less as a paralegal for him, drafting legal documents for his review and signature and doing deep research. Soon she was an irreplacable part of his office.

And then, in 1902, Chamberlain threw his hat into the ring for the Democratic nomination for Governor of Oregon. He won the job with a narrow majority, and then it was time to move to Salem.

Naturally, Chamberlain wanted his most valuable aide to come with him to the capitol. And when he was setting about building his cabinet, he appointed her to the position of Governor’s Private Secretary.

To modern ears, “Governor’s Private Secretary” sounds like a frivolous position at best — or maybe like the name of a “sexy” Halloween costume from that Spirit Halloween store that pops up in vacant storefronts every September. But that’s because for the last 100 years or so we have all gotten used to the idea of secretaries being little more than typewriter operators and call screeners. A secretary in 1902 was much more than that, more like a junior executive — a secretary in the “secretary of defense” or “secretary of state” sense of the word. In 1902 it was almost unprecedented for a woman to have the job of private secretary to a state governor. Caralyn may actually have been the first one in the nation.

Chamberlain served six years — one and a half terms — as Oregon governor with Caralyn Shelton by his side. His wife, Sallie Welch Chamberlain, had no desire to leave her social and family connections up in Portland and was more than busy with their seven children, so the Chamberlains maintained their home up in the big town for the family and George “batched it” in the governor’s mansion, traveling home as frequently as he could. Caralyn basically took over the social-secretarial functions of a First Lady so that Sallie could focus on her family up north.

In his book, historian Richard Roth says she and Chamberlain likely had a long-running affair during this time, and that may be so, but I’ve found nothing in my research that supports or even suggests this, and Salem has never been a town that can keep a secret, especially one involving both sex and partisan politics, for anywhere near that long.

Halfway through his second term in office, Chamberlain ran for a seat in the U.S. Senate and won the election. So he resigned his office as governor in favor of his Secretary of State, Frank W. Benson, and prepared to board an eastbound train to take his new seat.

There was a problem, though. The entire freshman crop of senators from all across the country, every new senator who had won the 1908 election, was slated to be sworn in and seated on March 4, 1909. As seniority was determined by the date of swearing-in, all those senators, including Chamberlain, would have equal seniority to one another … unless one of them arrived in D.C. late and missed the swearing-in. If that happened, the latecomer would be junior to all the other members of his incoming class.

And that was a problem because March 1 was the day Benson was scheduled to be sworn in as Oregon governor.

If Chamberlain stayed in Oregon through the end of his term, he wouldn’t arrive in D.C. until three or four days later, and he’d miss the swearing-in ceremony. That would mean that every other member of the incoming 1908 freshman class of senators would have seniority over him.

No problem; this had happened before, and the solution was an easy one. The incoming governor simply came in a few days early with the title of Acting Governor; then, when March 1 came along, he’d be sworn in for real.

But there was a problem this time. On Feb. 27 when Chamberlain boarded that eastbound train, Secretary Benson, who was already struggling with the recurring illness (possibly malaria) that would kill him three years later, was too sick to play his part.

Well, this wasn’t uncharted territory either. There was a contingency plan in place. If the Secretary of State couldn’t step in as acting governor for any reason, the job fell to … you guessed it … the governor’s private secretary.

And thus it was that, on Feb. 27, the state of Oregon became the first in U.S. history to have a woman governor.

March 1, 1909, was a Monday, and by 10 o’clock Benson was feeling well enough to take the oath of office and step into his new role; this brought Caralyn Shelton’s 49-hour political career to a triumphal end.

By the way, the newspapers in 1909 found this whole exchange highly amusing and covered the situation extensively. Governor Shelton made a point of telling them she would veto no bills, promulgate no executive orders, and grant no pardons during her term. As far as I’ve been able to learn, nothing much happened during her time in office; but if anything had, she would have been the state’s chief executive in charge of dealing with it. And it’s clear that everyone involved had total confidence in her ability to do so, if she had to.

And after Benson took over, Caralyn boarded a train to D.C. to take her place in Chamberlain’s office.

She served there in Chamberlain’s office in D.C. throughout his two terms as a Senator, and, when he was defeated for re-election in the 1920 “red wave” of anti-Woodrow Wilson votes (don’t get me started on THAT guy), settled down in D.C. in private practice. And in July of 1926, a suitable interval of time after Sallie Chamberlain’s death at age 70 …… reader, she married him.

This was, of course, another “first” — the first case of two former state governors marrying each other in U.S. history. By this time, Chamberlain was 72 years old, and Caralyn was a youthful 50. They had been friends and business partners for most of their lives.

George and Caralyn Chamberlain only got to live together as husband and wife for a few months. Shortly after (or possibly before; the records aren’t clear) the marriage, George suffered a paralytic stroke. He lingered on for some months after that, an invalid, being cared for by Caralyn; but in 1928, three days before their second wedding anniversary, he died.

Caralyn followed ten years later, on Feb. 2, 1936, at the age of 59. Oddly, none of the many obituaries that ran in newspapers around the state even mention her 49-hour term as governor!

A quick footnote: There is much confusion about Caralyn Shelton’s name. Newspaper articles about her, of which there were many, called her “Carolyn.” Her great-great niece, Anne Mitchell, told Bryan Vance of OPB that her birth name was Carrie, but that she changed it to Caralyn to sound more formal in her role as George Chamberlain’s top paralegal. In any case, the name used in her obituary and carved on her gravestone is “Caralyn,” so that’s what I have adopted for this story.

(Sources: The Central Railroad of Oregon, a book by Richard R. Roth published in 2015 by Heritage Quest Press; “The Governor who Couldn’t Vote: Why History Forgot Oregon’s First Female Head of State,” an article and news report published Feb. 27, 2019, by Oregon Public Broadcasting; “Heritage: Oregon’s first woman governor lasted a weekend,” an article by Kaylyn F. Mabey published on Feb. 12, 2015 in the Salem Statesman Journal; and a series of articles written by Dr. Kimberly Jensen and posted in April and May 2014 on Kimberly Jensen’s Blog.)

Finn J.D. John teaches at Oregon State University and writes about odd tidbits of Oregon history. His book, Heroes and Rascals of Old Oregon was recently published by Ouragan House Publishers. To contact him or suggest a topic: [email protected] or 541-357-2222.