William Webster, who served as both the director of the FBI and the CIA, has encountered various criticisms and controversies throughout his career, which could be seen as his "problem." During his time at the CIA, he was often viewed as an outsider to the agency's traditional culture, earning the nickname "Mild Bill" for his conservative and legalistic approach. This was in stark contrast to predecessors known for more aggressive intelligence tactics, leading some to argue that his cautious style might have restrained the CIA's effectiveness in certain covert operations. His focus on legal compliance and avoiding scandal was praised for maintaining the integrity of the agencies but also critiqued for potentially lacking the bold action needed to tackle national security threats.
 

In more recent times, Webster has been vocal about his concerns regarding potential appointees to high-level intelligence positions, particularly under a Trump administration. He has openly criticized the qualifications of candidates like Kash Patel and Tulsi Gabbard, citing issues of loyalty and experience. His opposition to these nominations at the age of 100 reflects his continued engagement in intelligence community matters, which some might view as admirable dedication while others might see it as an unwillingness to step back from the public stage. This involvement keeps him in the public eye, where his opinions on current political appointees have sparked debates about what constitutes appropriate leadership in intelligence.

The legacy of William Webster is a complex one, often debated in terms of his impact on both the FBI and CIA. His approach was one of lawfulness and restraint, which contributed to a period of relative stability and legal adherence but also drew criticism for possibly stifling innovation or aggressive action against security threats. Public perception of Webster varies; he's been celebrated for his integrity, receiving honors like the Presidential Medal of Freedom, but his cautious leadership style has been a point of contention. This duality in how his tenure is remembered might be encapsulated as "William Webster's problem" - a man who upheld the law and ethics of intelligence work while potentially missing opportunities for more assertive strategies in national security.