392 Oak St. 

644 University St. 

1134 Oak St. 

Possibly Wilhelm’s Portland Memorial Mausoleum and Funeral Home 

Leroy Bentley was born on 19 May 1876, in Polk County, Oregon, on the Donation Land Claim of his grandparents who came to Oregon in 1853.  His parents, John W. Bentley, a bootmaker, and Dora Bentley, then just 17 years old, faced challenges raising young Leroy. By 1880, at the age of 5, Leroy was living with his aunt and uncle, Eliza Jane (Bentley) Tweedale and W.C. Tweedale – a situation that may have provided him with a more stable upbringing.  

Leroy’s uncle W.C. Tweedale, was a notable figure whose life story captured public attention, as chronicled in his 1931 obituary in Albany’s Greater Oregon Newspaper. Growing up with such an intriguing family influence must have left an impression on Leroy.  

By 1896, Leroy, now using the name Roy, was living in Salem. Records indicate that by 1900, he worked as a spinner at the Thomas Kay Woolen Mill and boarded at 381 Mill St. It was at the woolen mill that he met Rachael Anna Gross, a fellow spinner and boarder. The two were married in 1902 in Multnomah County, Oregon.  

Roy left TKWM in 1909 to start a career in sales, initially working as a grocery salesman in Salem. By 1911, he and Rachael had relocated to Portland, where Roy embarked on a long career in the shoe business. He worked for Fithian and Barkel in Portland for more than forty years, with his final employment being at the Wright Shoe Store.  

Roy and Rachael never had children. Rachael passed away in December 1955, followed by Roy in January 1956. Both died in Portland, though their burial locations could not be determined.     

J W Bentley. Age: 33. Married HOH. Residence: Washington St, Albany, Oregon. Occupation: shoe and boot maker. Dora Bentley. Age: 33. Wife. Occupation: keeping house.     

1900  Roy Bentley. Age: 24. Birth: Apr 1876 in Oregon. Single, boarder at 381 Mill St. Father born in England. Mother born in New York. Occupation: Spinner. Household members: Ada Hudelson, age 32, HOH (no employment); Jay R Hudelson, age 7, son; Wayne Hudelson. age 4, son; Anna Gross, age 20, sister, spinner; Roy Bentley, age 24, boarder.   

1910  Leroy Bentley. Age: 33. Birth: abt 1877 in Oregon. Residence: rents home at 644 University, Salem, Oregon. Married HOH. Married 8 years. Father born in Arkansas. Mother born in Oregon. Occupation: Grocery salesman. Household members: LeRoy Bentley, age 33, HOH; Rachel Bentley, age 32, wife; Ruth Gibson, age 11, boarder.    

1920  Roy Bentley. Age: 44. Birth: abt 1876 in Oregon. Married HOH. Residence: Rents home at 318 Monroe St, Portland, Oregon. Father and Mother born in U.S. Occupation: Shoe salesman. Household members: Roy Bentley, age 44, HOH; Rachel Bentley, age 42, wife.    

1930  Roy Bentley. Age: 54. Birth: abt 1876 in Oregon. Married HOH. Residence: Owns home at 661 12th St, Portland, Oregon. No radio set.  Age at first marriage 27. Father born in Virginia. Mother born in Oregon. Occupation: Shoe salesman. Household members: Roy Bentley, age 54, HOH; Rachel Bentley, age 50, wife.   

1940  Roy Bentley. Age: 64. Birth: abt 1876 in Oregon. Married HOH. Residence: Rents home at 80 NE Tillamook, Portland, Oregon. Occupation: Retail shoe salesman. Highest grade completed 8th. Household members: Roy Bentley, age 64, HOH; Anna Bentley, age 62, wife.    

1950  Roy Bentley. Age: 73. Birth: abt 1877 in Oregon. Married HOH. Residence: 2612 Taylor/Yamhill, Portland, Oregon. Occupation: Retail shoe salesman. Household member: Rachel E Bentley, wife, age 72, born in Oregon.   

1878  W C Tweedale, grocer, 65 W 1st.   

Salem

1905  Roy Bentley, spinner, TKWM res 392 Oak. 

1907  Roy L Bentley spinner, TKWM res 1134 Oak. 

1911  Leroy Bentley, carpenter, bds 733 N Front.  

Portland

1911  Le Roy Bentley clerk, Dougherty-Fithian Shoe Co, h 10421/2 Grand Ave.    

1913  Roy Bentley, salesman, Dougherty Shoe Co, h 316 Fremont. 

1915  Roy Bentley (Rachal A) salesman, Dougherty Shoe Co, h 316 Fremont.   

1939  Roy Bentley (Rachael A) salesman, h 80 NE Tillamook  

Oregon Statesman 16 Nov 1909, p. 2 – Salem City Council appoints election clerk Roy Bentley for Ward Four.  

Greater Oregon, Albany 27 Jul 1945, p. 1 – Dora Bentley 88 dies in Idaho.  Most of her life was in Albany.  Survivors: son Roy Bentley of Portland, daughter Mrs. Harry Cronise of Pocatello, ID, and daughter Mrs. Maurice Winters of Portland.  

The Oregonian 29 Dec 1955, p. 18 – Rachael (Anna) Bentley death notice. Late of 2612 Taylor; wife of Roy Bentley, aunt of Wayne A. Huddelson, Margaret Gross Rogers and Annie V Rice.  Funeral services 29 Dec at Conservatory Chapel of A J Rose and Son, SE 6th and Alder.   

Oregon Daily Journal 23 Jan 1956, p. 4 – Roy Bentley obit.  Of Rt 1 Box 165, Portland died 21 Jan 1956.  Committal services at Portland Memorial.  Born in Polk County on donation land claim of his grandparents who came to Oregon in 1853.  He attended school in Albany.  Associated with Fithian and Barkel in Portland and SF for more than 40 years.  More recently worked for Wright Shoe store in Portland.  Member of the Irvington Masonic Lodge No 185 and Webfoot lodge, Woodmen of the World.  Survivors: two sisters including Mrs. Ethel Winter, Portland.   

WW1 Draft Card.  Roy Bentley 42 of 318 Monroe St, Portland OR.  b 19 May 1876.  Stock Clerk, Fithian and Berkel, 28 N 5th St, Portland, OR.  Build Stout.  Height Medium.  Hair Light.  Eyes Blue.  NOK Mrs. Roy Bentley same address.    

Oregon Death Record.  Ada Ann Gross Hudelson 71.  B 1870.  Died in Portland, OR on 7 Nov 1941.  Spouse George Gross.    

WW2 Draft Card.  Roy Bentley 65 of 7715 N Exeter Ave, Portland, OR.  B in Polk County, OR on 19 May 1876.  Employed by Zell Conwell, 812 SE Morrison, Portland, OR.  NOK Mrs. Rachael Anna Bentley same address.    

OR Death Record.  Anna Bentley, 76, 2612 SE Taylor St, Portland OR died of asphyxiation (gastric content) in Multnomah County on 24 Dec 1955.  B in OR on 13 Jan 1879.  Married, husband Roy.  Father George Gross.  Mother Sarah Sylvester.    

OR Death Record.  Roy Bentley, 78, Rt 1, box 165, Portland, OR died of a heart attack in Multnomah County on 21 Jan 1956.  B near Amity, OR on 19 May 1876.  Widowed.  Salesman for Wrights Shoes.