John Levi Skipper was born in Camden County, Georgia on November 23, 1826, the son of Martha Pearce. His maternal grandparents were John and Ann (Cain) Pearce. It is believed that his father's name was Gabriel Skipper. Martha Pearce in her family Bible noted that "John L. Pearce was born November 23, 1826." Also in 1902 when John L. Skipper applied for a pension based upon his Seminole Indian War service, he stated that he had been discharged from his company under the name of John L. Pearce. A number of years after the birth of John Levi, Martha Pearce married Joseph Mizell.

John Levi Skipper moved during the 1840s to Hillsborough County, Florida where on October 8, 1849 he married Elizabeth Jane Hollingsworth, daughter of Stephen and Elizabeth (Colwell) Hollingsworth. Born 1829 in Sampson County, North Carolina, she moved with her family to Alabama, Georgia and finally to Hillsborough County, Florida in 1842.

John L. Skipper was a farmer and cattleman in Hillsborough County. On May 29, 1850, he registered the JL brand for use on his cattle; the mark being "Poplar leaf in one ear, undersquare in the other." John L. and Elizabeth J. Skipper are shown twice on the 1850 census for Hillsborough County, once as family 88, again as family 111. At that time they were living in the Ichepucksassa-Simmons Hammock area.

By 1856 John L. Skipper and his family had moved to the Peas Creek area, settling on the stream, near the present site of Homeland. Their homestead appears on Ives' 1856 military map of Florida, being shown on the east side of the trail that led from Fort Carroll south to Fort Meade.

When the Third Seminole War broke out, John Levi Skipper enlisted in Capt. William B. Hooker's Independent Company of Florida Volunteers at Fort Meade on Jan. 3, 1856. They were mustered into federal service on Feb. 21, 1856 and served until Aug. 20, 1856. After Seminoles attacked the home of Willoughby Tillis on June 14, 1856, they retreated south to Peas Creek swamp. Lt. Streaty Parker led a detachment of men to pursue the Indians, and among his number was John L. Skipper. During the battle which followed on June 16, 1856, John Levi was wounded. A colorful account of this incident appeared in J. O. Parrish's Battling the Seminoles:

"Uncle John Skipper, who had walked a short distance along the bank, was fired upon by a lone Indian. The shot took effect in the muscle of his right arm but did not break the bone. "Looking to where the shot had come from, Skipper saw the old Chief standing between him and the river, holding his smoking gun but making no attempt to reload it.
"Seeing there was no escape, the old Chief called out, ‘Me see John. Me let no other Indian shoot John. Me friend.'
"Mr. Skipper called to the men, ‘Boys, I am shot.' Bring me another gun quick or the cuss will get away. "One of the men ran to him with a loaded gun and raised it to shoot the old Indian, who stood in plain view and in easy range, but Skipper's blood was up and he tried to take the gun away from the man, in spite of his wounded arm, insisted on doing the shooting.
"At first the Indian thought that Uncle John was trying to keep the man from shooting him and a grin overspread his features as he thought his ruse had worked, but when he realized the true situation, he dashed off at high speed for the near by the river. "As the Indian disappeared thru the dense willows growing on the high bank and dived into the water, Mr. Skipper had got the gun and as the Indian, who had swum under the water until his breath gave out, bobbed up, Skipper fired tearing a huge hole thru the top of the Indian's head. "'There, damn you,' said Uncle John. ‘I'll drag your carcass out of there mighty soon.' Later, in spite of his wounded arm, he dived into the river and dragged the body to shore, where he proceeded to cut the head off."

During the Civil War, John L. Skipper "was opposed to secession and voted against secession and did not voluntarily aid, abet or engage in the rebellion," according to an affidavit made by William Raulerson in 1888 in support of John Levi's application for a U. S. pension based on his service in the Seminole Indian War. Nevertheless, he enlisted about 1863 in Capt. F. A. Hendry's Company A, Col. J. C. Munnerlyn's Battalion and "did faithful service, never deserted, and surrendered at the final surrender," according to F. A. Hendry in an affidavit for his widow's application for a pension in 1907.

John expanded his cattle operations, and Polk County tax lists for 1862 show that he owned 730 head of cattle. After the Civil War, John and his family moved to Orlando in Orange County where they lived until 1871. During the post-war years, Mr. Skipper became identified with the Republican party, and some of his descendants have remained active in that organization.

After leaving Orange County in 1871, John Levi Skipper and his family moved to Manatee County in that area that is now Hardee County, several miles east of Zolfo Springs in the Crewsville settlement.

He applied for a pension based upon his service in the Third Seminole War, applying first in 1888 and again in 1892.

John L. Skipper died July 24, 1907, near Zolfo Springs. His obituary in the Bartow newspaper reads as follows:

"As we go to press news reaches us of the death of Mr. J. L. Skipper, Sr., who passed away at the home of his daughter, Mrs. M. A. Roberts, fourteen miles east of Zolfo, at the ripe old age of 81.
"Mr. Skipper …mov(ed) to DeSoto County some 35 or 40 years ago. For several years he has been very feeble being practically helpless. The cause of his death is attributed to old age.
"He was a man of high honor, and respected by all who knew him. His death occurred Wednesday night at 11:00 o'clock.
"Deceased leaves a wife and several children to mourn his demise, among them our townsman and postmaster, E. E. Skipper, and J. L. Skipper, Jr., postmaster at Lakeland."

On Dec. 28, 1907, Elizabeth J. Skipper of Zolfo applied for a pension as the widow of John Skipper from his service in Capt. F. A. Hendry's Co. E. E. Skipper and J. A. Johnson acted as her witnesses. George W. Hendry of Bartow and Frederick W. Varn of Fort Meade provided an affidavit that they had served with John Skipper.

On Feb. 4, 1908, the Board of County Commissioners of DeSoto County, consisting of R. L. Holzendorf, C. L. Keene, D. J. Farabee, D. S. Williams and J. H. Carlton, recommended that she be granted an annuity. On Feb. 29, her claim was approved for a pension at the rate of $120 per annum, with pay from Feb. 14.

Elizabeth Jane Hollingsworth Skipper died on Feb. 23, 1908. Both Mr. and Mrs. Skipper are buried in the Hart Cemetery, Hardee County, Florida.

They had the following children:

1. David Henry Skipper, born Dec. 8, 1850; died Sept. 28, 1921; married (1) Florida Ann Smith, Nov. 26, 1874; (2) Dolly Powell, Feb. 3, 1889.
2. Jonathan Shaw "Jack" Skipper, born March 4, 1854; died Sept. 28, 1905; married Letitia Guest, Jan. 3, 1880.
3. Enoch Eugene Skipper, born July 31, 1856; died Nov. 2, 1920; married Martha E. Blount, Jan. 25, 1882.
4. Stephen Skipper, born May 2, 1859; died April 27, 1942; married Mary Cornelia Hart, July 17, 1890.
5. Martha Ann Skipper, born Sept. 20, 1861; died Feb. 5, 1947; married James Irvin Roberts, Nov. 16, 1875.
6. Joseph Lee Skipper, born May 24, 1864; died Sept. 6, 1947; married Minnie Merritt Nunnally, May 7, 1891.
7. Thomas Cooper Skipper, born May 12, 1866; died young.
8. John Levi "Bud" Skipper, born June 19, 1867; died July 27, 1940; married Jessie Lee Carlton, Feb. 15, 1893.
9. Mary Jane Skipper, born May 19, 1871; died Dec. 7, 1954; married Samuel A. Hart, Dec. 19, 1890.
10. William Oscar Skipper, born Nov. 10, 1873; died Jan. 10, 1954; married (1) Bertha Pearl Hart, Jan. 20, 1895; (2) Bertha Herzog Saunders, July 3, 1919.