At first, the former officials said, Mr. Shulkin and Mr. Bowman viewed the three men as allies with connections in the business and health care worlds. But the three men barraged the secretary with criticisms and suggestions, including many that had little basis in fact.
They once called the secretary with complaints about a $200 million contract that did not exist, according to the official who had to hunt for the nonexistent paperwork. Another time, according to documents obtained by ProPublica, they asked the secretary to solve a problem for a friend’s son that was an issue with the military, not veterans affairs.
By late 2017, the relationship with Dr. Shulkin had begun to sour. The Mar-a-Lago crowd had reservations about a $10 billion contract the department was preparing to sign for an electronic health record system. Dr. Moskowitz had used a similar system by the same company, Cerner, and did not like it.
The department assembled panels of experts to address the concerns, but the three men pushed to kill the deal. Eventually, the secretary, frustrated by their constant demands, decided to move ahead on his own.
“That is where his problems started,” one senior staff member said.
Dr. Shulkin had also split with political appointees over how to oversee privately provided health care. In December, the Florida advisers and the political appointees formed a plan to change leadership. The details were revealed in a memo left on a copy machine in January: Mr. Perlmutter would help get the secretary replaced. They would also replace the deputy secretary and chief of staff.
Dr. Shulkin tried to fight back, meeting several times with the White House chief of staff, John F. Kelly, but neither the secretary nor Mr. Kelly had authority to fire the appointees, according to one of the former officials.
Dr. Shulkin, who was facing criticism over lavish travel spending, was fired in March, shortly before he planned to finalize the Cerner deal.