Donald Trump is set to make his inaugural appearance as president at Saturday's annual White House Correspondents' Association dinner in Washington, an event poised to cast a stark public light on his administration's often-strained relationship with the media.

His presence at the gathering, hosted by the very journalists who cover his administration, will be under intense scrutiny. Historically, presidents attending this dinner have used the platform to champion free speech and the First Amendment, often interspersing their remarks with good-natured jabs at individual reporters.

Notably, the Republican president bypassed the event throughout his first term and the initial year of his second.…