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Following his retirement from West Point, Caslen was in January 2019 appointed as chief accountability officer at the University of Central Florida to oversee the reformation of the finance and administration operations, a position from which he resigned in May.

On July 19, 2019, Caslen was selected as the 29th President of the University of South Carolina. He was initially among a group of four finalists for the position. While Caslen was reported to be the front-runner, there was significant controversy about his nomination, given that he does not possess an earned doctorate and because of alleged comments made during open campus sessions regarding binge drinking and sexual assault; among faculty and students, 82% opposed Caslen's candidacy. It was later discovered by the Charleston Post and Courier that Mr. Caslen's name was added to the finalist list only after the intervention of the Chairman of the Board of Trustees as Caslen was not originally a finalist or an agreed upon alternate nominated by the presidential search committee. On April 26, the university Board of Trustees decided to reopen the search. However, it was revealed on July 8, that South Carolina Governor Henry McMaster was urging members of the Board to meet by the end of the week to vote on Caslen's candidacy for President. This caused further controversy, with the university's faculty senate unanimously passing motions to formally criticize the lack of transparency in the search process and to issue a vote of no confidence in Caslen to lead the university.. Several alumni and donors also opposed the intervention of the governor in the presidential search; notably businesswoman Darla Moore, writing as "the largest donor to the university and the namesake of one of the largest schools," urged the board to abide by the April 26 decision to continue the search. and the SACS Commission on Colleges opening an inquiry into the search to determine if there was undue outside influence. One trustee, Egerton Burroughs, believed that the opposition to Caslen was entirely political, stating, without evidence, "A lot of the people that are demonstrating are from out of town. I heard some of that Kamala Harris crowd is there … got this thing all tied into the Democratic primary," though Burroughs was unaware his comments were being broadcast. Despite the opposition of faculty and students, on July 19, Caslen was elected as the 29th President of the University by the Board of Trustees by a vote of 11–8, with one member voting "present".

Following his selection, Caslen stated that he recognized "the challenges the board addressed to get to this point" and expressed he would "listen to all of our students, faculty, staff, board members, and all our constituents." On July 22, 2019, Caslen held a press conference to announce his desire to raise the profile of the university by boosting the school's rankings, improving diversity, bolstering research, and beating in-state rival Clemson University in more athletic competitions. He also met with students, faculty, donors, and lawmakers, pledging to listen and learn. Caslen formally took office as the 29th President of the University of South Carolina on August 1, 2019. On October 7, the SACS Commission on Colleges announced that it had opened an official inquiry into Mr. Caslen's selection as university president, SACS notified the university that there was "evidence of a significant accreditation-related issue" and opened a formal investigation into whether or not there was undue external influence on the search. Caslen himself acknowledging that the inquiry was legitimate and that trust between himself and the wider university community had been damaged. Though stated that the theSACS inquiry would result in no formal sanctions, the report did state that there was, in fact, undue political influence from the Governor in the selection of Mr. Caslen; Governor McMaster's office denied the finding by arguing that the Governor's influence is permissible as he is a member of the board of trustees ex officio. The University will be subject to enhanced monitoring, a compliance report, and a site visit in Fall 2020.

During Operation Desert Storm, Caslen served as executive officer of the 2nd Battalion, 187th Infantry, 101st Airborne Division (Air Assault).

Caslen was appointed as Superintendent of the United States Military Academy on July 17, 2013. After five years of service, in April 2018 it was announced that Caslen would retire later in the year. In July, the army announced Lieutenant General Darryl A. Williams as Caslen's successor. The ceremonial relinquishing of command took place on June 22, 2018.

From May 2008 to December 2009, Caslen served as commander of the 25th Infantry Division. In October, he returned from a tour with the division in the Iraq War. Prior to this, he had served two tours in Afghanistan and one tour in the Gulf War. In December 2009, Caslen was nominated to be a lieutenant general in conjunction with his nomination to be Commandant of the United States Army Command and General Staff College at Fort Leavenworth which took effect in March 2010. In July 2011, Caslen was nominated to be chief of Office of Security Cooperation in Iraq.

Caslen was at the Pentagon during the September 11 attacks. Following the attack, he re-entered the Pentagon, helping search for wounded and working on reversing the air conditioning system in order to remove smoke from the building. Caslen was also chief of staff of the 10th Mountain Division (Light) (2003) at Fort Drum; assistant division commander (Maneuver) of the 3rd Infantry Division (Mechanized) (2004); deputy director for the War on Terrorism, J-5, the Joint Staff (2005 – June 2006); director of the Joint Staff's Detainee Affairs Division and commandant of cadets for the Military Academy at West Point, a post he left in May 2008. Caslen was chief of staff for the Combined Joint Task Force 180 in Afghanistan from May through September 2002. He was a commander of Operation Champion Sword.

Caslen served as brigade operations officer, 3rd Brigade, 101st Airborne Division (Air Assault); J-3 in Honduras for Joint Task Force Bravo in 1998; executive officer to the deputy commander in Haiti during Operation Uphold Democracy in 1994–1995; commander of the 1st Battalion, 14th Infantry, 25th Infantry Division (Light); senior brigade C2 observer/controller, Operations Group, Joint Readiness Training Center; chief of staff of the 101st Airborne Division; and commander of the 2nd Brigade, 101st Airborne Division (1999).

Caslen was born in Connecticut, and grew up in Connecticut, Massachusetts, and Vermont. In 1971 he graduated from North Country Union High School in Newport, Vermont. He graduated from the United States Military Academy at West Point in 1975 and played center for the Army Black Knights football team. He also earned a master's degree in business administration from Long Island University, and in 1989 he received a Master of Science degree in industrial engineering from Kansas State University. Caslen also received an honorary doctorate from Long Island University.

Robert Louis Caslen Jr. (born November 30, 1953) is the 29th and current President of the University of South Carolina. He is a retired United States Army officer who served as the 59th superintendent of West Point from 2013 until 2018. Between January and May 2019, Caslen was Senior Counsel to the President and Interim Chief Financial Officer at the University of Central Florida. On July 19, 2019, the Board of Trustees of the University of South Carolina elected him as the school's 29th President, a position he assumed on August 1, 2019. Caslen now serves as HigherEchelon's Special Advisor on Executive Leadership and Character Development.