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The Tailhook Convention of 1991 involved the U.S. Navy in a bitter controversy over allegations that officers had engaged in numerous acts of excessive drinking and sexual misconduct. The episode cast a shadow not only on the specific individuals involved, but on the Navy's overall culture—especially its treatment of women.

The term tailhook refers to the device on naval aircraft that catches the flight deck cables during their recovery onboard an aircraft carrier. The Tailhook Association is a semi-official organization of naval aviators, endorsed by, but not a part of, the Navy. The group's annual conventions enjoyed a longstanding reputation for being boisterous affairs. However, the Tailhook Association argued that its conventions were an important Navy tradition. Besides the revelry, its members used the event to build relationships within the naval aviation community as well as to instill the important traditions of that culture.

Naval aviation first became a distinct warfare community after World War II. Since naval aviation appeared to have a highly significant role in the postwar world, its officers acquired a reputation for being among the Navy's elite. Although many of its traditions were consistent with older service values, naval aviation developed a culture that was in many ways unique within the Navy. The popular expression “work hard, play hard” reflected what was the foremost value of this community. Flying off aircraft carriers demanded very high degrees of skill and precision; despite the intense training, accidents still occurred even to the most proficient of pilots. The dangerous lifestyle bred a mentality that naval aviators were entitled to certain rewards. For example, naval aviators were not as observant of the chain of command as officers in other warfare communities. The camaraderie of flying transcended the traditional barriers of rank and position within the Navy.

The stereotypical aviator supposedly kept up a social lifestyle that was more glamorous than that of his peers in the surface Navy. Aviators drove fast cars, consumed large amounts of alcohol, and dated the most attractive women off-duty. Although clearly a stereotype, such behavior occurred often enough to maintain a sense of privilege for naval aviators within the aviation community and the Navy at large. Many of these perceptions were captured in the popular 1986 movie Top Gun. The film's box-office appeal encouraged some naval aviators in the 1980s and 1990s to adopt such stereotypical daredevil behavior to an even greater degree. Taken to an extreme, this type of culture nourished behavior that was boorish, reckless, and misogynistic. Within this environment, women were seen as yet another reward for the dangerous missions carried out by male aviators, who generally did not conceive of women as their professional equals.

Other operational and organizational issues in the Navy also helped to frame the context of the 1991 Tailhook Convention. This particular meeting was the first to take place after the Persian Gulf War. Naval aviators had flown numerous dangerous missions in support of the air campaign, the success of which many observers were crediting for the short duration of the conflict. Naval aviators had also been the service's only casualties from the war. Afterwards, Tailhook participants appeared to want even more than usual opportunities to recuperate and relax from the wartime stress. Navy leaders were also considering substantial changes to the roles of women in the service. Prior to 1991, female aviators were not assigned to carrier-based squadrons, even though some of them were qualified pilots in these aircraft. Women were excluded from these roles because it could involve them in combat; however, the restrictions also tended to limit their career opportunities. Many male aviators resented any attempts to reverse the status quo.

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