Ina Dell Cleaveland was born on 23 December 1882 in Flint, Steuben County, Indiana. Conflicting evidence states that Ina was born on 22 December 1882 in Flint, Steuben County, Indiana.¹ She was the daughter of George David Cleveland and Nancy Jane Kirkland. She married Leroy Roberts, son of Ziba Roberts and Louisa Collins, on 26 January 1898 in Jackson Twp, Steuben County, Indiana.¹ She died on 3 July 1924 in Jackson Twp, Steuben County, Indiana.² She was buried on 6 July 1924 in Jackson Prairie Cemetery in Jackson Twp, Steuben county, Indiana, Jackson Prairie Cemetery is near the town of Orland (Mill Grove Township) but just inside Jackson Township.

     Willis Russell Roberts was born on 18 September 1903 in Jackson Twp, Steuben County, Indiana. He was the son of Leroy Roberts and Ina Dell Cleaveland. He married Mary Benfer on 23 July 1928 in Angola, Steuben County, Indiana. His wife Mary died on 16 November 1989. He married Vivian Overholt on 11 December 1991 in Angola, Steuben County, Indiana. He died on 28 October 2003 in Lakeland Nursing Center, Angola, Steuben County, Indiana.²

Following is extracted from an article which appeared in the September 13, 2003 Angola Herald-Republican; written by Amy Oberlin. Permission to republish obtained:

Man to celebrate 5 scores
Centenarian reflects on his life in education

“If you had half as much and two times as many plus two and a half more, you’d have enough to make a score.”

That’s the problem Willis Roberts liked to spring on classes when he visited them as Steuben County superintendent of schools between 1936 and 1949. Today, he noted, not many people know that a score is 20. But those who do should be able to deduce that the answer to Roberts’ equation is seven.

On Thursday, Roberts will officially add another year onto his long life. And that will equal 100.
Roberts may not hear very well and his eyesight isn’t the greatest, but his mind seems as sharp as anyone half his age. Due to his immersion in the county school system, he knows, or knew, many people in the area and is a wealth of Steuben County history. “He’s always been such a vibrant person,” said his neighbor, Margaret Smith. “He’s such a delightful person ... such a kind gentleman ... He’s done a lot for the community.”

“I learned more there than any place else, I think,” he said. He started his schooling at the age of 5, and attended the rural school for eight years. His teacher, Sara Davis, lived in a house on his parents’ property. “All the woman teachers that taught there stayed at our house,” said Roberts. “All the men teachers drove in.” School wasn’t nearly as close to Roberts as his teacher was. The one-room building was four miles from his home. “It was for you to get there as best as you could,” Roberts said. “I didn’t walk, I ran four miles across country, sand burrs and all.”

After primary school, Roberts attended Flint High School. Then, he went to Tri-State Normal College, now Tri-State University, for two years to earn his teaching degree in 1926. In 1930, he earned his bachelor’s degree from Manchester College. His master’s degree came from Indiana University in 1932. Then, after already spending 24 years learning, “I taught school for 45 years,” said Roberts.

Roberts taught for 15 years and then was elected county superintendent of schools in Steuben County, holding that position for 13 years. From there, he went to the Huntertown school system, now Carroll High School, where he taught for 17 years. He started his career teaching U.S. history and government to high schoolers. He also coached basketball and baseball.

“I taught English. I taught math. I taught physical education,” Roberts said. His favorite subject? “Like the boy said, recess,” Roberts joked. He probably liked teaching math the best, he said.

At that time, there were eight high schools in Steuben County: Salem Center, Flint, Orland, Pleasant Lake, Fremont, Metz, Scott Center and Hamilton. Twelve township trustees were charged with electing a superintendent. The election, Willis said, seemed to run along party lines and when he was up for the post, there were six Democrats and six Republicans. “The county auditor cast a vote if there was a tie,” he said. “His wife and my wife were pretty good friends ...”

When Roberts became the county superintendent, he traveled frequently between the various school sites. “A lot of the tests were run off by my secretary on a mimeograph,” said Roberts. “I’d deliver them.”

Over the years, Roberts got to know many local families, though he says most of the people he knew are now gone. “Some of the kids I had in school are in their 90s now,” he said. Roberts and his wife, Vivian, whom he married in 1991, live at the same property he’s lived at since 1928. The white house on U.S. 20 was built by his father-in-law, Oliver Benfer, and Willis lived there with his wife, Mary. Willis has many memories of their life together, and quietly is building new memories with Vivian.... They live together in a small, one-story house on the property on U.S. 20, while Lee and Connie Downey live in the original farm house as caretakers.

“I’ve known Willis about all my life,” said Connie, who moved to Angola from Muncie after Vivian suffered a fall about a year ago. “Mary and Willis and her parents are like another family.”.^3,4,5

     Iona Mary Cleaveland was born on 19 October 1871 in Flint, Steuben County, Indiana.^2,3 She was the daughter of George David Cleveland and Nancy Jane Kirkland. She married George Moses Emerson on 30 April 1896 in Steuben County, Indiana.⁴ She died on 2 July 1929 in Pleasant Lake, Steuben County, Indiana.

The farm that Iona and her husband worked and raised their children on was just north of Salem Center, Indiana, and in 1990 was owned by Burnette Lease. Her death certificate reports the cause of death as "Drowning, suicide".

     Andrew Cary Cleaveland was born on 4 September 1877 in Flint, Steuben County, Indiana.^2,3 He was the son of George David Cleveland and Nancy Jane Kirkland. Andrew Cary Cleaveland also went by the name of Cary. He married Annie Pearl Graves, daughter of Thomas Leander Graves and Xantha May Logan, on 24 October 1901. Andrew and Annie were divorced circa 1916.⁴ He died on 23 July 1948 in Kendallville, Noble County, Indiana. He was buried in Lake View Cemetery in Kendallville, Noble county, Indiana.⁵

Cary was a railway mail clerk in Kendallville. The 1900 census listing shows him living as a boarder with Mr. and Mrs. William Wilbett (Willett?) on Diamond Street with that occupation. He met his wife at this time; her brother was the Mayor of Kendallville and her father had been the Mayor some years before. They separated about 1920 (the 1920 census shows no Andrew Cary Cleveland living in Indiana). Later, before WWII, Cary was into chicken farming in Louisiana, but didn't succeed in the business. During the war he worked in the Kaiser shipyards in California. He returned to Indiana after the war, staying for a while with Maynard and Tudy (his daughter) Pray. According to Maynard, he was very smart but somewhat of an alcoholic, and spent a lot of time "down at the Elks Club." He started a garage in Kendallville. He spent some of his time writing congressmen with his "Oliver" typewriter.⁶

      Ruth Laurine 'Tudy' Cleaveland was also known as Laurine. She was born on 15 August 1902 in Kendallville, Noble County, Indiana.³ She was the daughter of Andrew Cary Cleaveland and Annie Pearl Graves. She married Maynard Allen Pray on 8 November 1932 in Albion, Noble County, Indiana. She died on 7 February 1986 in Kendallville, Noble County, Indiana.⁴ She was buried in Lake View Cemetery in Kendallville, Noble county, Indiana.⁵

Her mother gave her the nickname; she was probably named after Grover Cleveland's daughter Ruth, according to Maynard Pray. A photo taken in Milwaukee in the fall of 1917 shows a person named "Ruth" which looks the age she would have been with the John Monroe Cleaveland family. It is possible that this was during the period after her parents had separated (her father was in California for a time and then in Loisiana about that time). Later she was a beach guard at Bixley Lake for a time, and taught school.

     Maynard Allen Pray was born on 31 July 1905 in Kendallville, Noble County, Indiana. He married Ruth Laurine 'Tudy' Cleaveland, daughter of Andrew Cary Cleaveland and Annie Pearl Graves, on 8 November 1932 in Albion, Noble County, Indiana. He died on 2 April 1997 in Kendallville, Noble County, Indiana.⁴

While Maynard was in his late teens he had a job at a bank in Kendallville, where he earned about $10 for a six-day week. Then at 21 he spent about a year as a roofer and carpenter in Florida. He then went to work for the McCray company, who sent him to Atlanta in 1932 as an office boy. There he was paid $22.50 a week and his apartment cost $35 per month. He returned home and after a while as a gravel truck driver he returned to work for the McCrays, where he stayed for a total of 40 years. He owned a gas station on (old) U.S. Route 6; after the highway was rerouted the station was rebuilt into the home in which he lived until his death.

     He married Leslie Ann Cleaveland, daughter of LeRoy Adams Cleaveland and Pearl Ann Miller, on 22 March 1987 in Marlboro, Monmouth County, New Jersey. Ron and Leslie were divorced on 19 May 1988 in Union County, New Jersey.

     Dorcas Wilson was born on 29 January 1656/57. She married Aaron Cleveland, son of Moses Cleaveland and Ann Winn, on 26 September 1675 in Woburn, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the New England Confederation.¹ She died on 29 November 1714 in Cambridge, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the Province of Massachusetts Bay.

     Aaron Cleveland was born on 10 January 1653/54 in Woburn, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the New England Confederation. He was the son of Moses Cleaveland and Ann Winn. He married Dorcas Wilson on 26 September 1675 in Woburn, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the New England Confederation.¹ His wife Dorcas died on 29 November 1714. He died on 14 September 1716 in Woburn, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the Province of Massachusetts Bay. He was buried in the Old First Burying Ground in Woburn, Middlesex county, Massachusetts Bay Colony. Aaron was a housewright.

     Abigail Waters was born on 29 November 1683 in Woburn, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the New England Confederation. She married Aaron Cleveland, son of Aaron Cleveland and Dorcas Wilson, on 1 January 1700/1 in Woburn, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the Province of Massachusetts Bay.¹ Her husband Aaron died on 1 December 1755. She died on 6 January 1761 in Norwich, New London County, the Connecticut Colony.

     Aaron Cleveland was born on 9 July 1680 in Woburn, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the New England Confederation. He was the son of Aaron Cleveland and Dorcas Wilson. He married Abigail Waters on 1 January 1700/1 in Woburn, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the Province of Massachusetts Bay.¹ He died on 1 December 1755 in Norwich, New London County, the Connecticut Colony. Aaron was an innkeeper.

     Susannah Porter was born on 26 April 1716 in Medford, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the Province of Massachusetts Bay. She married Aaron Cleveland, son of Aaron Cleveland and Abigail Waters, on 4 August 1739 in Medford, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the Province of Massachusetts Bay.¹ She died on 28 March 1788 in Salem, Essex County, Massachusetts.

     Aaron Cleveland was born on 19 October 1715 in Medford, Middlesex County, the Massachusetts Bay Colony, which at that time was part of the of the Province of Massachusetts Bay. He was the son of Aaron Cleveland and Abigail Waters. He married Susannah Porter on 4 August 1739 in Medford.¹ He died on 11 August 1757 in Philadelphia, the Pennsylvania Colony. Aaron was a minister.

     Abiah Hyde was born on 9 January 1748/49 in Norwich, New London County, the Connecticut Colony. She married Aaron Cleveland, son of Aaron Cleveland and Susannah Porter, on 12 April 1768 in Norwich, New London County, the Connecticut Colony.¹ She died on 23 August 1788 in Norwich, New London County, Connecticut.

     Aaron Cleveland was born on 2 February 1743/44 in East Haddam, Middlesex County, the Connecticut Colony. He was the son of Aaron Cleveland and Susannah Porter. He married Abiah Hyde on 12 April 1768 in Norwich, New London County, the Connecticut Colony.¹ His wife Abiah died on 23 August 1788. He died on 21 September 1815 in New Haven, New Haven County, Connecticut. Aaron was a minister.

     William Cleveland was born on 20 December 1770 in Norwich, New London County, the Connecticut Colony. He was the son of Aaron Cleveland and Abiah Hyde. He married Margaret Falley on 19 December 1793 in Westfield, Hampden County, Massachusetts.¹ He died on 18 August 1837 in Black Rock, Erie County, New York. William was a silversmith.

     Margaret Falley was born on 15 November 1766 in Westfield, Hampden County, the Massachusetts Bay Colony, which at that time was part of the of the Province of Massachusetts Bay. She married William Cleveland, son of Aaron Cleveland and Abiah Hyde, on 19 December 1793 in Westfield, Hampden County, Massachusetts.¹ Her husband William died on 18 August 1837. She died on 10 August 1850 in Black Rock, Erie County, New York.

     Richard Falley Cleveland was born on 19 June 1804 in Norwich, New London County, Connecticut. He was the son of William Cleveland and Margaret Falley. He married Ann Neal on 10 September 1829 in Baltimore, Baltimore County, Maryland.¹ He died on 1 October 1853 in Holland Patent, Oneida County, New York. Richard was a minister.

     Ann Neal was born on 4 February 1806 in Baltimore, Baltimore County, Maryland. She married Richard Falley Cleveland, son of William Cleveland and Margaret Falley, on 10 September 1829 in Baltimore, Baltimore County, Maryland.¹ She died on 19 July 1882 in Holland Patent, Oneida County, New York.

     Stephen Grover Cleveland was born on 18 March 1837 in Caldwell, Essex County, New Jersey. He was the son of Richard Falley Cleveland and Ann Neal. He died on 24 June 1908 in Princeton, Mercer County, New Jersey.
Twenty-second and twenty-fourth President of the United States; inaugurated March 4, 1885, served one term, succeeded by Benjamin Harrison, inaugurated again in 1893 and succeeded in 1897 by McKinley. He was Governor of New York 1883-1885. His first name was dropped in early childhood. As President he enlarged the civil service and vetoed many pension raids on the treasury. His second term saw a severe depression and labor troubles. It is suspected that one or more Clevelands reverted to the Cleaveland spelling of their names to dissociate themselves with the President. According to the syndicated "Trivia Quiz" he performed as a hangman during the period he was sheriff of Erie Co, NY.²