The Dogs of Looser Island

The Dogs of Looser Island

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The Dogs of Looser Island
The Dogs of Looser Island
Episode 16: The Girl at the Tiller

Episode 16: The Girl at the Tiller

Olga takes action.

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Shari Lane
Jun 28, 2025
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The Dogs of Looser Island
The Dogs of Looser Island
Episode 16: The Girl at the Tiller
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Recap and Reminders

Celia Prewitt has a secret. It may or may not be related to her granddaughter Olga, who fearlessly plies her wooden sloop Blossom over the Salish Sea, having learned a love of sailing from her grandmother. Or Paulo’s disappearance. Or the fact that the ghost of her Pug, Hubert, remains a constant companion.

Whatever it is, Celia’s secret is one of the reasons she hopes to teach nineteen-year-old Charlie to “make music, not war.”

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You can find the Cast of Characters on this Substack or on The Dogs of Looser Island website here.

Photo by LordRunar from Getty Images (image altered to reflect the story)


Celia Prewitt suffers from insomnia.

Sleepless nights bring their own version of the First Circle of Hell. (Teaching literature to high school students had at least provided her enough literary chops to think of her life in terms of Dante’s The Divine Comedy.)

It starts with a question, maybe even a question she didn’t know she had, and it nibbles at her just as she’s drifting off. One question feeds another, and another, and then she is fully awake, with no hope of sleeping, so she gets up, and makes herself a cup of tea and a bit of toast.

When young people like Olga have insomnia, Celia knows, there’s always a cellular phone involved, to while away the time until sleep is once again possible. Celia has no desire for Goggling information on the internet (she’s pretty sure that’s what they call it), or social media, though all her children have asked her to join so she can keep up with her grandchildren without the necessity of a phone call or—heaven forbid—an actual letter.

For Celia, a quiet conversation with Hubert while she sips her tea and eats her toast is sufficient. Hubert is a good listener, and sometimes indicates by the wag or droop of his tail or the way he cocks his head whether he thinks she’s on the right track or should go back and start her analysis again.

Sometimes he even comments on the issues at hand, usually with sailing lingo, just to make her smile. I think you’ve flogged that idea to the bitter end . . . The wind is flagging, watch your point of sail . . . You’re no longer becalmed, that must buoy your spirits . . .

He loyally keeps her company while she grapples with the conundrum o’ the day, but more often than not, the answers continue to elude her.


When Paulo née Pelabo was here (more properly Paulo né Pelabo, though few people know the correct masculine version), thoughts about laws and immigration kept Celia awake.

Mrs. Prewitt taught her children, both her own and those in her classrooms, to obey the rules, even when compliance was the more difficult choice. Only if obedience was truly immoral was the mandate lifted. During her years in the classroom, Mrs. Prewitt shepherded many a spirited discussion about where the line should be drawn as between rigid legalism and moral relativism, and those discussions echoed in her mind whenever thoughts of Paulo prevented sleep.

There was a way to apply for legal entry into the United States. The asylum process, in particular, was strengthened after WWII because America turned away some refugees from Nazi Germany, sent them back to be slaughtered.

If this young man was fleeing adversity, shouldn’t he have applied for asylum?

And what if he wasn’t really a refugee? What if he just sauntered over the border to get a job with better pay? Was that alone really a justifiable excuse for skirting the law?

Then again, what did this line of reasoning mean for her own ancestor’s “excuse” (fleeing marriage to a malodorous cattle rancher)?

And how much did Ella and Markus and Lauren even know about him? What if he was a liar, or a thief, or worse?


From the beginning of the saga, Celia was pretty certain she knew Olga’s take on Paulo’s situation, but if she’d had any doubts they were cleared up one bright October afternoon.

It was Halloween, and Olga was visiting. (Whenever Halloween fell on a weekend, she’d drive up from Seattle and take the ferry over to join the extravagant Looser Island Monster Mash. She always dressed as a Piratess, though every year there were variations on the theme: one year an eye patch and wooden sword; one year multiple strings of stolen “booty” i.e. fake pearls, and a fake diamond tiara; one year a tiny black leather skirt, fishnet stockings, thigh-high boots, with a plastic hook in her left hand.)

In the morning, as Olga headed out for a sail, Celia called, “Pick up some English muffins for me, will you dear?” and Olga said, “Of course, Nona,” and came back to give her a peck on the cheek before leaving.

It was one of those fall days when the sun burnished every surface so you’d remember what sunshine feels and looks like over the long, cold, rainy winter to come, and Celia and Hubert were enjoying every minute of it when, later that afternoon, Olga burst through the front door, visibly windblown from sailing and tempest-tossed from within.

“I think I just overheard someone calling ICE about Paulo,” she said.

She threw herself down on the aging sofa but quickly got up again and strode around the room, clearly unable to sit still while she recounted the story.

“I’m not a hundred percent sure who it was,” she said, “but there was this guy talking on his cell phone in the Apple Cart parking lot, obviously trying to keep his voice down. But also he shouted a couple of things because, well, you know, Nona . . . nobody gets good cell reception on Looser Island. Anyway, he had his back to me and his hood up over his head, so I couldn’t get a good look at his face, and I could barely hear him when he wasn’t shouting, so I didn’t know, at first, if it was a local, but as I walked past I heard the guy say, ‘No, immigration,’ and then, when I kind of hung around, you know, kind of looking like I was just stopping to rearrange the groceries in my backpack, he said, ‘I don’t know, I just thought someone should report it. I mean him.’”

Olga hadn’t wanted to stare at him directly, she told her grandmother, for fear the man would know she was listening and would walk away from her, making her attempts at eavesdropping more difficult. She described the man’s stature and voice and clothing, and then she said, “I don’t want to believe it, Nona, but it sounded and looked kind of like Bill.”

“Bill Butteford? Lauren’s son?” Celia said. “That seems unlikely. Pelabo’s—all right, fine—Paulo’s help at the Apple Cart is what allowed Bill to escape to the mainland again. Why would he jeopardize that?”

Olga’s description was vague enough that it could have fit any number of people. It was certainly possible that, among the two thousand or so souls on the island, at least one did not agree that harboring an undocumented immigrant, an illegal, was a moral imperative.

Olga was furious, and wanted to call Sheriff Tom.

“And what would you ask him to do, Olga?” Celia said, gently. “He can’t arrest someone for reporting a crime.”

Olga squeezed her eyes tight in a visible effort not to cry. Finally she stomped her foot, suddenly an angry toddler again. “This is so stupid!” she declared. “I’m not going to just sit here and wait for ICE to pick up Paulo and chuck him into detention.”

“What are you going to do?” Celia said, genuinely curious to see what her smart, brave, impetuous granddaughter would do.

Hubert looked up expectantly, too.

“I’m not sure,” Olga said grimly. “But I’ll think of something.”

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