In 1869 the Baptist Female College moved its operation to the former home of Pony Express Founder William B. Waddell at the corner of 13th and South Streets.
However, Lexington's educators, business leaders and ministers had made numerous attempts to establish a school for boys and young men.
A local editorial writer proclaimed that Wentworth was "One of our oldest, most generous and most worthy citizens" and "no nobler name can this community furnish [the new school]. "
On May 24, 1880, Mr. Wentworth bought the "New Presbyterian Church" at the southwest corner of 18th and Main Streets, directed that it be fitted up for the next term, and gave the school solid financial backing.
Although his financial involvement was limited to the Academy's early years of operation, his foresight led to the establishment of the first board of trustees and his generosity provided a firm foundation for the school.
Wentworth also announced that 22-year-old Benjamin Lewis Hobson, the son of the local Presbyterian minister who had run a fledgling private boys’ school in town the previous year, would be given charge of W.M.A.
Benjamin Hobson knew that he could not operate the new school alone, and he turned to Sandford Sellers, a 26-year-old friend and former classmate at Centre College in Kentucky.
In the early days, he handled all the institution's administrative affairs, academic planning, and student recruitment on his own, canvassing surrounding areas on horseback.
The Kansas City and St. Louis newspapers referred to the gridiron battle as the "Little Army-Navy Game", and gave front-page coverage to the outcome.
The cadet corps stood in review for the President before he attended a reception at the home of COL Sellers for the unveiling of a Mariners' Compass created in terrazzo tile by the Academy art instructor, Max Harper.
Wentworth was dealt an additional blow when, in 1975, a fire destroyed two buildings and severely damaged others, causing the loss of over 32,000 square feet (3,000 m2) of space.
On April 7, 2017, the Board of Trustees announced that Wentworth Military Academy & College would be closed, with final commencement to occur on May 13, 2017 and the official date of closure set for May 31, 2017.
The 43 acre campus and buildings were sold to Jubilee University (a Christian based music boarding school) which has since maintained the facilities for their ongoing instructional operations.
Saved from the auction block for museum display were several large historic items, including the chapel's stained glass windows, and the actual WWI "Doughboy" statue which stood in front of the campus since 1921 and was traditionally saluted by every cadet when they passed by it.
The Higher Learning Commission placed Wentworth on probation in late 2015 "because of concerns related to integrity regarding the College's finances and resources to support its academic programs and operations.
Following its closure in May 2017, the campus was put up for sale and purchased in June of 2020 by Jubilee University, a Christian music and performing arts organization based in St. Louis.