The plan called for the demolition of existing structures and construction of new commercial buildings in much of the downtown area, including that now occupied by Leadership Square.

The collapse of Penn Square Bank in 1982 and softening oil market created tenancy concerns and the design was reduced.

[6][7] The building, when constructed in 1984, was owned by Metropolitan Life Insurance Company and managed by CB Richard Ellis.

[8] The Leadership Square building replaced, in part, the seven-story Local Federal Savings and Loan tower, built in 1958.

In 2000, major tenants included Bank of America, Massachusetts Mutual Life Insurance Company, Merrill Lynch, Paine Webber, Smith Barney, and Grant Thornton, as well as local law firms McAfee & Taft, Phillips McFall McVay, and Gable & Gotwals.

Leadership Square's major tenants were Bank of America, McAfee & Taft, Phillips McFall McVay, Massachusetts Mutual Life Insurance Co., Merrill Lynch, Paine Webber, Smith Barney, Gable & Gotwals Attorneys and Grant Thornton.

The building has a two-level 340-car parking garage and a direct connection to the Oklahoma City Underground green tunnel.

[21][22] In 2017, the OKC Over the Edge fundraising event for the Central Oklahoma Habitat for Humanity involved rappelling from the top of Two Leadership Square.