James Madison Chiles was a colorful real estate developer of the Kenilworth neighborhood, which he modeled on the Kenilworth Castle in England.
James Madison Chiles was thought at the time to be stubborn and delusional, with his grand ideas for developing Kenilworth. This 1925 article, however, belatedly credits him with being an important visionary and contributor to the history of Asheville. The article states:
Kenilworth Park, Kenilworth Inn, the town of Kenilworth, those assets which have been of incalculable benefit to Asheville, represent the metamorphosis of a dreamer’s air castles into the solid creations they assume today. When Mr. Chiles used to outline his visualization, many of his more practical friends interpreted his portrayal as a delusion….There is no element of invidiousness in the declaration that Jake Chiles occupied a niche in Asheville’s expansion which he shared with no other.
The luxurious hotel which sweeps and dominates the panorama for miles around, the happy homes that range from modest cottages to palatial castles, the winding roads of labyrinthine allurements, the gigantic dams and reinforced bridges, the blooming foliage made accessible to mankind, the avian melodies with which the park’s hills reverberate, these and all other things connected with Kenilworth are easily discernible now and gloriously delightful.
From the Jan. 22, 2015 Asheville Citizen Times:
James Madison Chiles, developer of Kenilworth, leads a tour of the planned neighborhood he began advertising in 1913. “Forest worshipers!” he addressed readers, “the natural forest trees are still on the ground — and go with the lots.” Another fact: the neighborhood will include a “tourist hotel, golf links, lake, (and) floral gardens.” Romanticism and real estate went together like a horse and rider in Chiles’ imagination. Chiles’ horse was Kenilworth’s road designer. The lake was Chiles’ idea, and it trumped his partners’ wish for a golf course. Read more about Jake’s ideas in Kenilworth Community.
What didn’t fly was Chiles’ plan to embed an Excalibur replica into a stone. Rebuilding Kenilworth Inn, destroyed by fire in 1909, was a resurrection, “Phoenix-style.” Chiles experienced a fire in Asheville’s Langren Hotel on Sept. 14, 1914, residing there while preparing to marry Leah Arcouet and build their house in Kenilworth. “Man in bed,” he reported to Leah in a letter, “opened his baby blue eyes, saw sparks as big as Plymouth Rock Hen eggs hopping around on his bed.” “I’ve been as busy as a hen scratching for food,” he wrote her the previous day, concluding, “I just heard a hen cackle, back in a few minutes.” Jan. 22, 2015 ACT
Jake Chiles was an avid horseman and lover of automobiles and was one of the first persons from Asheville to make a cross country drive. He dabbled in a number of business ventures.
Jake Chiles received 6 out of 7 votes for Mayor of Kenilworth in May 1915. The 7th voter was either “out to lunch or ill in bed.” Mayor Chiles vowed to clean up Kenilworth and stated that the man who failed to vote will probably be found in the hospital at the end of the week.
Before building his Spanish Revival Villa on Chiles Avenue, Jake Chiles built and lived in an Arts and Crafts home built in 1914 at 87 Kenilworth Avenue.
Jake Chiles died at his home on June 1, 1925 at the age of 55.