Why are there twenty-five Helena Drives in Brentwood? One rumor says a developer cheated on his wife Helena, then apologized by naming every street in her honor. Cute story, not true. The cul-de-sacs were laid out in 1922 on the Brentwood Country Club Estates tract, owned by Richard P. Shea (1868-1932), whose wife was named Elizabeth. (They soon split and he married Jane McComas in 1924.) Shea simply borrowed “Helena” from nearby Helena Street, which originated in 1907. That was on the Carlos Heights tract, set up by Chicago hotelier Tracy C. Drake (1864-1939), whose Blackstone and Drake hotels still operate in the Windy City. Since Drake named Carlos Heights for his son Carlos, it follows that his streets were tributes to other loved ones: Anita Avenue may be for his wife Annie and Helena Street may be for his sister Helen Vernera Drake (1867-1960), a Chicago socialite. (I have no guesses for Carmelina Ave.) Coincidentally, Richard P. Shea had a daughter named Helen, so his 25 Helena Drives could be for her. Tragic postscript: On Christmas Eve 1932, two months after his wife Jane’s death, a despondent Shea tied her ashes around his neck and drowned himself in the Pacific.
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