Colonel Kaifesh is a native of suburban Chicago, Illinois. He graduated from Indiana University and was commissioned in 1991. As a Second Lieutenant, he was assigned to Lima Company, 3rd Battalion, 5th Marines, where he served as a Rifle Platoon Commander, Weapons Platoon Commander, and Company Executive Officer. In 1994, he became the 5th Marine Regiment, Tow Platoon Commander.
In 1996 he transitioned into the Marine Corps Individual Ready Reserve and in 1999 reported to Golf Company, 2nd Battalion, 23rd Marines to serve as the Executive Officer. In response to September 11, 2001, he was assigned as the Assistant Operations Officer for 2nd Battalion, 23rd Marines supporting Operation NOBLE EAGLE.
In 2003, he took Command of Golf Company, 2nd Battalion, 23rd Marines in support of Operation IRAQI FREEDOM I and Task Force Tripoli’s mission to secure the city of Tikrit, Iraq. From 2004 to 2005, he served as a Team Leader with the 3rd Civil Affairs Group, supporting Operation IRAQI FREEDOM II in Al Anbar, Iraq and participated in Operation VIGILANT RESOLVE in Fallujah.
From 2006 to 2007, he was assigned to Multi-National Security Transition Command – Iraq, under Multi-National Forces – Iraq supporting, Operation IRAQI FREEDOM IV and served as the Deputy for a Joint Intelligence Transition Team manning, training and equipping the Iraqi National Information and Investigation Agency, modeled off of the U.S. FBI.
From 2007 to 2008, he was assigned to the Naval War College in Newport, Rhode Island where he completed his M.A. in National Security and Strategic Studies. In 2008, he was appointed to the Office of Legislative Affairs where he served as a Legislative Fellow and Military Legislative Assistant to Congressmen John Kline (MN-02).
In November 2009, he assumed command of 3d Battalion, 25th Marines and led the battalion on its deployment to Afghanistan in support of Operation ENDURING FREEDOM 10.2. Upon relinquishing command in November 2011, Colonel Kaifesh checked into I MEF (FWD) to assume the responsibilities of the C9, Governance Officer during the Afghanistan deployment supporting Operation ENDURING FREEDOM 12.1.
In October 2012, Colonel Kaifesh was assigned to the Joint Staff in the Anti-Terrorism, Homeland Defense Directorate as an Action Officer and later served as the Battle Captain for the Chairman of the Joint Chiefs of Staff in the National Joint Operations and Intelligence Center in the Pentagon.
In April 2014, Colonel Kaifesh took command of the 2d Civil Affairs Group in Washington D.C. In July 2015 he became the J5 Lead Planner for CENTCOM Forward – Jordan. Upon returning from his deployment to Jordan in 2016, he was assigned to Headquarters Marine Corps and filled the role as the RAM Special Enabler Monitor. In March 2017, he became the MARCENT Coordination Element – Kuwait, Officer in Charge. In May 2018, he became an Instructor for the MAGTF Staff Training Program and retired in May 2019.
Since April 2019, Colonel Kaifesh was Commandant of the Hyman G. Rickover Naval Academy and later Marine Leadership Academy.
His personal decorations include the Bronze Star, Defense Meritorious Service Medal (x2), Meritorious Service Medal (x2), the Navy and Marine Corps Commendation Medal with Combat “V,” the Navy and Marine Corps Achievement Medal, and the Combat Action Ribbon.