The Loyal Legion intentionally maintains a hierarchical leadership structure, with the Commander-in-Chief at the acme. He presides over the Commandery-in-Chief consisting of various subordinate offices that help ensure the smooth operation of the Order. Past Commanders-in-Chief occupy an important place in the organization by providing wise counsel to current officers, volunteering for standing committees, and serving in state Commandery leadership.

The following list details over 160 years of unbroken leadership to the Loyal Legion:
Paul Thomas Davis, 2025–Present
Michael Timothy Bates, Esq., 2023–2025
Col. Robert Darnell Pollock, USAF (Ret.), 2021–2023
Joseph Thomas Coleman, Ed.D., 2019–2021
Col. Eric Armando Rojo, USA (Ret.), 2017–2019
Capt. James Robert Simmons, USAF (Ret.), 2015–2017
Waldron Kintzing Post, 2013–2015
Jeffry Christian Burden, Esq., 2011–2013
Keith Graham Harrison, 2009–2011 (SUVCW CinC, 1994–1995) *
Karl Frederick Schaeffer, 2007–2009 *
Benjamin Charles Frick, Esq., 2005–2007
Douglas Reed Niermeyer, 2003–2005 *
Gordon Rick Bury II, 2001–2003 (SUVCW CinC, 1986–1987)
Col. Robert James Bateman, USA (Ret.), 1999–2001 *
Hon. Michael Patrick Sullivan, 1997–1999

The Rev. Can. Robert Girard Carroon, Ph.D., 1995–1997
Hon. Scott Wallace Stucky, USAFR (Ret.), 1993–1995
Henry Nathan Sawyer, 1991–1993 *
Lowell Varner Hammer, Jr., 1989–1991 (SUVCW CinC, 1991–1992) *
William Henry Upham, 1985–1989 (Last CinC to serve more than one term) *
Alexander Purves Hartnett, 1983–1985 *
Lt. Col. Philip Marsh Watrous, USA (Ret.), 1981–1983 *
Thomas Nesbitt McCarter III, 1977–1981 *
Col. Joseph Blair Daugherty, USA (Ret.), 1975–1977 *
Charles Allan Brady, Jr., 1973–1975 *
Col. Brooke Montgomery Lessig, USAR (Ret.), 1971–1973 *
Lt. Col. John Thomas Lenahan O’Connell, Sr., Esq., USAR (Ret.), 1967–1971 *
Col. Walter Everett Hopper, Jr., Esq., USAR (Ret.), 1964–1967 *
Maj. Gen. Clayton Barney Vogel, USMC (Ret.), 1964 (Last general/flag officer to serve as CinC) **
Lt. Col. Henry Durston Saylor II, USAR (Ret.), 1962–1964 *
Lt. Col. Donald Macy Liddell, Jr., USAR, 1961–1962 ***
Maj. Gen. Ulysses Simpson Grant III, USA (Ret.), 1957–1961 (SUVCW CinC, 1953–1955) *
Cmdr. William Carroll Duval, USNR (Ret.), 1953–1957 *
Donald Hollis Whittemore, 1951–1953 *
R. Adm. Reginald Rowan Belknap, USN (Ret.), 1947–1951 *
James Vernor, Jr., 1942–1947 (First CinC who did not serve in the U.S. Armed Forces) *
Maj. Gen. Malvern Hill Barnum, USA (Ret.), 1940–1942 **
Col. William Innes Forbes, Sr., USA (Ret.), 1935–1940 ***
Col. Hugh Means, USA, 1933–1935 *
Capt. William Parkinson Wright, USA, 1931–1933 (Last Civil War officer to serve as CinC. GAR CinC, 1932–1933) *
Bvt. Maj. George Mason, USA, 1930–1931 *
Brig. Gen. Samuel Warren Fountain, USA (Ret.), 1930 **
Mstr. Robert Means Thompson, Esq., USN, 1927–1930 **
R. Adm. Purnell Frederick Harrington, USN (Ret.), 1925–1927 *
Lt. Gen. Nelson Appleton Miles, USA (Ret.), 1919–1925 **
Lt. Gen. Samuel Baldwin Marks Young, USA (Ret.), 1915–1919 *
R. Adm. Louis Kempff, USN (Ret.), 1915 *
Bvt. Brig. Gen. Thomas Hamlin Hubbard, USA, 1913–1915 **
Col. Arnold Augustus Rand, Esq., USV, 1912–1913 (First non-general/flag officer to serve as CinC) *
Lt. Gen. Arthur McArthur, Jr., USA (Ret.), 1912 **

R. Adm. George Wallace Melville, USN (Ret.), 1911–1912 **
Lt. Gen. John Coalter Bates, USA (Ret.), 1909–1911 *
Maj. Gen. Grenville Mellen Dodge, USA, 1907–1909 *
Maj. Gen. John Rutter Brooke, USA (Ret.), 1905–1907 *
Maj. Gen. David McMurtrie Gregg, USA, 1903–1905 *
Lt. Gen. John McAllister Schofield, USA (Ret.), 1899–1903 *
R. Adm. Bancroft Gherardi, USN (Ret.), 1896–1899 *
Maj. Gen. John Gibbon, USA (Ret.), 1895–1896 **
Brig. Gen. Lucius Fairchild, USA, 1893–1895 (GAR CinC, 1886-1887) *
R. Adm. John Jay Almy, USN (Ret.), 1893 *
Bvt. Maj. Gen. & President Rutherford Birchard Hayes, USA, 1888–1893 **
Gen. of the Army Philip Henry Sheridan, USA, 1886–1888 **
Bvt. Maj. Gen. & President Rutherford Birchard Hayes, USA, 1886 *
Maj. Gen. Winfield Scott Hancock, USA (Ret.), 1879–1886 **
Maj. Gen. George Cadwalader, USA (Ret.), 1865–1879 **
* Deceased
** Died In Office
*** Resigned