WASHINGTON — Robert Wilkie, President Trump’s choice to lead the Department of Veterans Affairs, is a conservative Washington insider who would bring three decades of military policymaking and a deep list of Capitol Hill connections to a Cabinet post responsible for serving one of the administration’s most crucial constituencies.

But when he appears Wednesday for his Senate confirmation hearing, Wilkie also will draw on a career spent working shoulder to shoulder with polarizing figures in U.S. politics and often defending their most divisive views.

Wilkie, 55, has impeccable credentials: Three decades at the center of the country’s most important military policies. The son of an Army artillery commander severely wounded in Vietnam – and a reserve officer in the Air Force himself. A trusted lieutenant of Defense Secretary Jim Mattis with contacts in Congress spanning at least five administrations.

He started as a young aide to Jesse Helms, R-N.C., the five-term Senate firebrand who denounced Martin Luther King Jr. and once called gay people “weak, morally sick wretches.” He served as a top aide to Senate Majority Leader Trent Lott, R-Miss., who lost his leadership post after defending a fellow senator’s segregationist campaign for president decades earlier. And he joined the inner circle of former defense secretary and Iraq War architect Donald Rumsfeld before returning to the Pentagon last year to run military personnel policy for the Trump administration.

Throughout, Wilkie showed a willingness to fight on the front lines of his bosses’ culture wars. Earlier this year he led efforts to justify Trump’s near wholesale ban on transgender troops. In 1997, he rebutted a Democratic proposal to ensure equal pay for working women. And in 1993, he publicly defended a failed push by Helms to support an organization whose logo included the Confederate flag.

Wilkie grew up visiting U.S. battlefields with his father and developed a lifelong fascination with military history, including that of his ancestors, who fought for the Confederacy. He was, as recently as 2005, a fixture at the annual memorial ceremonies in Washington held by descendants of Confederate veterans around the birthday of Jefferson Davis. Wilkie also was a member of the Sons of Confederate Veterans, a group that defends public displays of the Confederate symbols.

A Pentagon spokeswoman said Wilkie no longer attends the ceremonies or counts himself a member of the group. In a statement, Wilkie said the commemorations were once a means to memorialize soldiers but now have become “part of the politics that divide us.”

Paul Rieckhoff, founder of Iraq and Afghanistan Veterans of America, a leading advocacy group, said Wilkie must demonstrate that he doesn’t hold antiquated views and that he can serve all veterans. “He has to show he is loyal to veterans and not a partisan agenda,” Rieckhoff said.

Wilkie declined to be interviewed for this story.