As one of President-elect Donald Trump’s closest and most consistent allies, Sen. Jeff Sessions is a likely pick for a top post in his administration. But when Sessions faced Senate confirmation for a job 30 years ago, it didn’t go well, The Associated Press reported Thursday.

Nominated for a federal judgeship in 1986, Sessions, R-Ala., was dogged by racist comments he was accused of making while serving as U.S. attorney in Alabama. He was said to have called a black assistant U.S. attorney “boy” and the NAACP “un-American” and “communist-inspired.”

Sessions was the first senator to back Trump during the campaign and is an architect of Trump’s immigration, counterterrorism and trade policies. His name has been floated for attorney general and secretary of defense. The Trump transition team released a statement Thursday saying the president-elect is “unbelievably impressed” with Sessions, citing his work as a U.S. attorney and state attorney general in Alabama.

But confirmation for the four-term lawmaker, even in a Republican-controlled chamber, is not guaranteed.