The Howard clan seems to have left North Carolina and migrated to Robertson County, Tennessee, early in the 1800s. Wiley William Howard married Aurora O. "Anna" Johnson (1816–1884) in Tennessee on February 9, 1838. They were farming in Texas, at Sherman in Grayson County, by 1860. Wiley died before 1870.

Wiley and Anna had three known children: Gustavus A. Henry "Gus" Howard (1847–1904); Joshua E. Howard (1850–1935); and Florence Miranda Howard (1854–1931).

Gus and Florence married siblings. Florence married Wyatt T. Cutler (1851–1915) in 1874. The wedding of Gus and Laura Alenda Cutler (1861–1925) took place in 1881. Thus the Howards and the Cutlers became closely linked.  Gus married a woman named much later, in 1898, Joshua married a woman named Frances L. or "Fannie."

Wyatt and Laura Cutler were two of the eight children of Dr. Thomas Nicholson Cutler and Emeline Cartwright Cutler. Dr. Cutler had three more children by a second wife, Almira Jack. The doctor received his medical training at Allspath Medical College in New Orleans and served the Confederacy in the Civil War. He trained as a minister and settled in Grayson County, Texas, where he preached for thirty years at the Primitive Baptist Church in Tioga. He died in Tioga in 1896.

The Sunday Gazetteer
Sunday, June 12, 1887

By 1887, both Joshua Howard and Wyatt T. Cutler had left their Sherman farms and were living in nearby Denison, a rowdy railroad boom town. That year, the Denison City Directory listed Wyatt as city marshal. He was living at 331 West Bond Street; presumably Florence was with him. Wyatt's younger brother, "Tom" Cutler, was in Denison, too, operating Cutler's Saloon at 126 West Main Street. He lived at 721 West Chestnut.

1887 Denison City Directory

Bailey & Howard Drug Store

Sunday Gazetteer
Sunday, June 12, 1887

Still single in 1887, Joshua E. Howard had two businesses in downtown Denison. In partnership with Dr. Daniel H. Bailey, "physician and surgeon," he had opened the Bailey & Howard drug store at 406 West Main. Bailey, who was official City Physician, had his office and residence above the store. He and Joshua advertised that Bailey & Howard Drugs, as "The Leading Druggists, carry a large assortment of Wall Paper, Decorations, Paints, Oils, &c." In addition, with George McLagan, Joshua had formed Howard & Company, real estate agents, at 118 West Main. Joshua was living at 811 West Chestnut.

406 West Main Street

Drug Store
408 West Main Street

Four years later, in 1891, the City Directory found Gus H. Howard in Denison, too. Living at 501 North Fannin Avenue, he and partner Christopher G. Kircher owned the Buck Horn Saloon at 117 West Main. Dr. Bailey and Joshua Howard had gone separate ways. Dr. Bailey had teamed up with Samuel W. Culpepper to run the drug store, now in a new building next door at 408 West Main. The doctor lived and saw patients upstairs. Apparently Joshua Howard had decided to stay behind at 406 West Main and focus on his real estate and insurance business, in partnership with Thomas E. Reardon. Having married Fannie in 1898, Joshua lived at 527 West Woodard Street. Reardon boarded with the R. S. Legate, longtime head of First National Bank.

1891 Denison City Directory

Howard & Reardon
Real Estate, Insurance and Collection Agents
406 West Main Street

1896 Denison City Directory

In 1896, Gus was proprietor of the State National Exchange Saloon at 302 West Main, next door to the State National Bank; he was living at 112 West Gandy. Working with Gus at the saloon were Wyatt Cutler and his son Roscoe. Howard & Reardon's basic business remained stable, allowing Joshua to partner with Gus to operate Howard Race Track beyond the city limits on East Main Street. Joshua boarded at 317 West Crawford Street.

The 1900 Census reflected changes in Wyatt T. Cutler's life. His experience as city marshal and city councilman had led to a post as "district judge." He had also moved to an uptown address, 1021 West Woodard Street. There were seven children at home. One, son Roscoe, continued working as a bartender.

1901 Denison City Directory

In 1901, the City Directory showed Howard & Reardon holding steady. Gus was not working, and wife Laura was offering furnished rooms in their home at 230 West Gandy. That year, Wyatt was justice of the peace for Denison's Precinct No. 2, with an office upstairs at 302 West Main. Roscoe lived with his parents and worked as a bartender at Michael Sweeney's bar, a center of local politics since the days when Justin Raynal held forth at the same location.

1903 Denison City Directory

Wyatt Cutler passed away on September 15, 1903, and was buried at Fairview Cemetery. Gus joined him there a few months later, passing away in October, 1904. Following Fannie's death in 1919, Joshua seems to have retired to Southern California. The 1930 Census had him as a lodger at Stillwell Hotel in Los Angeles. He died on May 10, 1935, and was interred at Fairview Cemetery in Denison.