The original Grim Reapers were activated on June 3, 1942 as VF-10 at NAS San Diego flying the F4F Wildcat. The first commanding officer was James H. Flatley fresh from the Battle of the Coral Sea. He became known as "Reaper leader". The Grim Reapers deployed with USS Enterprise (CV-6) to the Southern Pacific in 1942 where they participated in the Battle of Guadalcanal. After their return to the U.S. and NAS Sand Point they transitioned to the F6F-3 Hellcat and once again deployed to the South Pacific aboard the Enterprise. During their second combat tour, VF-10 participated in operations in the Marshall Islands, Jaluit, Emirau, Western Caroline Islands, Hollandia, Truk Lagoon and the Battle of the Philippine Sea (Marianas Turkey Shoot). The squadron returned to the East Coast at NAS Atlantic City and transitioned to the F4U-D Corsair and took part in strikes against Ryukyu Islands, Kyūshū, Okinawa and the Wake Island. VF-10 returned to NAS Alameda where it was deactivated in November 1945.
By the end of 1962, the Skyray and the Demon had been phased out in favour of the F-4 and Detachment A was disestablished and the F-4 training moved to NAS Key West. On May 1, 1966 a new detachment was formed at NAS Oceana which took over the training of replacement pilots and RIO’s in the areas of aerial refuelling, carrier qualification and conventional weapons. The Key West unit concentrated on air-to-air combat, missile firing and radar intercept techniques. In August 1967 VF-101 introduced the second generation F-4, the F-4J, to squadron service. VF-101’s administrative command, Readiness Attack Carrier Air Wing 4, was disestablished on June 1, 1970, with VF-101 shifting control of Command Fleet Air Key West, but this moved lasted only a year, and the Grim Reapers moved from NAS Key West was completed with a detachment remaining at Key West. Their third change of control happened in July when they moved under the command of Commander Fighter Wing One at NAS Oceana.
In January 1976 VF-101 began operating and instructing aircrews and maintainers in the F-14 Tomcat as well as the F-4. NAS Oceana had two fleet Tomcat squadrons (VF-14 and VF-32) that had transitioned at NAS Miramar at VF-124. VF-101 now took responsibility to transition the rest of the Oceana based Phantom squadrons as well as train pilots and RIOs fresh from flight school. The first two Oceana F-4 squadrons, (VF-41 and VF-84), to transition to the F-14 at VF-101 began in June.
In 1975 and 1976 the Grim Reapers were awarded the CNO Aviation Safety Awards and in November 1976 the unit received its fourth Safety Citation due to 36 continuous months without accident. As the Navy got more and more F-14s, it was decided to form separate units for both F-14 and F-4 training and on August 5, 1977 VF-101 was split into two squadrons. VF-101 continued to train F-14 crews on the east coast while a new squadron VF-171, was established to carry on the F-4 east coast training. VF-171 was disestablished in 1984 after the last two Oceana F-4 squadrons (VF-74 and VF-103) turned in their Phantoms and began to transition to the Tomcat.
In 1986, VF-101 had completed 3 years of accident free operations earning them another Safety Citation and in March 1988 they received a third CNO Safety Award. The same year, VF-101 began to receive the F-14A+ (now F-14B), which cured the most serious problem of the F-14, that of sensitive, underpowered and troublesome engines, the new engines also had improved fuel economy and 14,600 pounds-force (65,000 newtons) of thrust over the F-14A. The new fuel economy gave the F-14B one third more time on-station and sixty percent more range. On September 12, 1990 VF-101 opened another new door for the F-14, dropping Mark 84 bombs. Due to these efforts, the F-14 community was trying to persuade policy makers to restart the F-14 production, but instead it led to the F-14’s role as a strike fighter, rather than an air-to-air fighter.
VF-124 was disestablished in 1994 and VF-101 became the sole F-14 Fleet Readiness Squadron (FRS) and created a detachment at NAS Miramar to train crews and ground personnel on the F-14A and D. Until 2002, when VF-213 moved from Carrier Air Wing 11 (Pacific Fleet) to Carrier Air Wing Eight (Atlantic Fleet), the F-14D had only been flown by west coast squadrons). The aircraft of the Miramar detachment were all numbered in the 200 series reflecting their VF-124 heritage while those based in Oceana were numbered in the 100 series. When NAS Miramar became MCAS Miramar in 1996, all F-14 squadrons were moved to NAS Oceana, as well as the VF-101 detachment, although VF-101 maintained its NAS Key West detachment until VF-101 was disestablished. VF-101’s weapons training encompasses a whole range of air-to-ground weapons, from general-purpose bombs, cluster bombs, laser-guided bombs, air-launched decoys, JDAM weapons and air-to-air weapons.
Several VF-101 aircraft also featured the markings of disestablished F-14 squadrons—among them were VF-1, VF-21, VF-24, VF-33, and VF-74. As the only F-14 FRS until its disestablishment in 2005, VF-101 at one point had as many as 130 F-14s of all three variants as well as a small number of T-34 Mentors for currency training and range control work.
Fittingly, the honored guests at the VF-101 disestablishment ceremony were the surviving members of the Flatley clan that created the Grim Reapers and could boast of three generations of Grim Reaper pilots. The folded Grim Reaper squadron flag was folded and presented to the family for safekeeping with hopes that another Grim Reaper squadron will be created in the future.