For 30 years, Emily T. Gail has thrived in paradise: Kailua-Kona on the Big Island of Hawaii. While her address has been in the Aloha State, however, her heart has remained in Detroit.
As have several of her possessions.
“I’ve kept a storage unit here for 30 years!” says Gail, the perpetually grinning entrepreneur, race organizer, columnist, sports broadcaster, real estate agent, and beloved gift shop owner who made “Say Nice Things About Detroit” an eternal part of this city’s emotional psyche, over lunch at a Corktown deli. She’s in town to attend her 60th class reunion at Grosse Ile High School and the annual, invitation-only Detroit Homecoming event she helped create. But she’s never needed a special occasion to return home.
“I’d come a month at a time,” she reveals. “Stay at the same motel. Room 129. Then fly back to Hawaii.” Her frequent flyer miles are about to decrease, however, because Emily Gail is returning to Detroit for good.
She’s coming home to stay.
A recent auto accident has slowed her timetable, but Gail hopes to be a full-time Motor Citizen sometime this year. “I’m a paper hoarder,” she confesses. “I’ll probably need to shovel out my condo.”
In in the early ’80s, she and her partner, the late Herb “Pooh” Squires, became one of the first couples to participate in the Ironman Triathlon in Hawaii. Then in 1986, they were recruited to organize the race due partly to the success of the Emily Detroit Run, a footrace they founded — the first ever held on our downtown streets — which took place from 1975 until the late ’80s and had swollen to 20,000 participants by that time. They never returned. So why move back now?
Two big reasons. Though she says she’s in excellent health, she’s 78 and believes the quality of care in metro Detroit would be superior to Hawaii’s going forward. And she feels the need to be closer to family.
Gail says she’s spending time with her twin sister, Edee, and her brother Max (yes, that Max Gail, forever in our TV hearts as Wojciehowicz from Barney Miller), who has four kids and grandchildren. Most of her four other siblings and relatives are scattered across the U.S. Living on the mainland will make travel easier, and there’s nowhere she’d rather reside than here.
Detroit history even lives in her name. “[Veteran Detroit business editor] R.J. King was writing his book Detroit: Engine of America and told me, ‘Your relative was one of the first mayors of Detroit,’” Gail relates. “Charles Trowbridge. My middle name is Trowbridge. That’s what the ‘T’ stands for. The Trowbridge House on Jefferson? That’s my family.”
She felt tied to Hawaii because one of her cats, Pono Boy, had diabetes and needed continuous care; he died last year at 18. Meanwhile, she had “Say Nice Things About Detroit” copyrighted after Shinola, among many others, took liberties with the phrase. (They subsequently named a watch after her, “The Gail.”)
However, Gail now thinks she may have “adapted” the line from an old campaign to “Say Nice Things About Hawaii.” Uh … who doesn’t? “You’d be surprised,” she says. “‘We didn’t like our hotel,’ or ‘The waves were too high — we couldn’t swim.’ People are people.”
To read the full 2025 City Guide, visit hourdetroit.com/cityguide.
This story originally appeared in the April 2025 issue of Hour Detroit magazine. To read more, pick up a copy of Hour Detroit at a local retail outlet. Our digital edition will be available on April 7.
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