The accident board stated that Bud Holland's personality significantly influenced the crash sequence. USAF personnel testified that Holland had developed a reputation as an aggressive pilot who often broke flight safety and other rules. The rule breaking included flying below minimum clearance altitudes and exceeding bank angle limitations and climb rates.
 
An earlier incident occurred in 1991 when a B-52 piloted by Holland performed a circle above a softball game in which Holland's daughter was participating. Beginning at 2,500 feet (760 m) AGL, Holland's aircraft executed the circle at 65° of bank. Described by one witness as a "death spiral," the nose of the aircraft continued to drop during the maneuver and the bank angle increased to 80°. After losing 1,000 feet (300 m) of altitude, Holland was able to regain control of the aircraft.
 
During a May 19, 1991, air show at Fairchild, Holland was the command pilot of the B-52 aerial demonstration flight. During the demonstration, Holland's aircraft violated several safety regulations, including exceeding bank and pitch limits, flying directly over the air show spectators, and possibly violating altitude restrictions. The base and wing commander, Colonel Arne Weinman, along with his staff, observed the demonstration but apparently took no action.
 
On July 12, 1991, Holland commanded a B-52 for a "flyover" during a change of command ceremony for the 325th Bomb Squadron at Fairchild. During both the practice and the actual flyover, Holland's aircraft flew at altitudes below 100 feet (30 m)—well below the established minimum altitude—, flew steeply banked turns in excess of 45°, exceeded pitch angle limits, and executed a wingover. The wingover was not specifically prohibited but was not recommended because it could damage the aircraft. After witnessing the flyover, Colonel Weinman and his deputy commander for operations, Colonel Julich, verbally reprimanded Holland but took no formal action.
A B-52H takes off with a standard pitch attitude.
 
During the May 17, 1992, Fairchild air show, Holland was again the command pilot of the B-52 aerial demonstration flight. During the demonstration, Holland's aircraft again violated several safety regulations, including several low altitude steep turns in excess of 45° of bank and a high pitch angle climb, estimated at over 60° nose high which Holland finished with a wingover maneuver. The new wing commander, Colonel Michael G. Ruotsala, apparently took no action. One week later, the new deputy commander for operations (DO), Colonel Capotosti, on his own initiative warned Holland that if he (Holland) violated any more safety regulations, Capotosti would ground him (remove him from flying status). Capotosti did not, however, document his warning to Holland or apparently take any other kind of formal action.
 
On April 14 and April 15, 1993, Holland was the mission commander of a two-ship (two B-52 aircraft) training mission to a bombing range near Guam in the Pacific Ocean. During the mission Holland flew his aircraft closer to the other aircraft than regulations allowed. Holland also asked his navigator to videotape the bombs falling from the aircraft from inside the aircraft's bomb bay, also against regulations. Holland's navigator later brought the video to the attention of three Fairchild USAF leaders. The first, Lieutenant Colonel Bullock, the current 325th Bomb Squadron commander, did not do anything about it and may have even tried to use the videotape for blackmail to coerce the navigator into accepting a position as mission scheduler for the wing. The second, the deputy operations group commander, Lieutenant Colonel Harper, told the crew member to conceal the evidence. The third, the DO, allegedly responded to reports of the video by stating, "Okay, I don't want to know anything about that video -- I don't care."At the August 8, 1993, Fairchild air show, Holland once again commanded the B-52 demonstration flight. The demonstration profile once again included bank angles greater than 45°, low altitude passes, and another high pitch climbing maneuver, this time in excess of 80° nose high. The climb was so steep that fuel flowed out of the vent holes from the aircraft's wing tanks. The new wing commander, Brigadier General James M. Richards, and the new DO, Colonel William E. Pellerin, both witnessed the demonstration but neither took any action.
 
On March 10, 1994, Holland commanded a single-aircraft training mission to the Yakima Bombing Range to provide an authorized photographer an opportunity to document the aircraft as it dropped training munitions. The minimum aircraft altitude permitted for that area was 500 feet (150 m) AGL. During the mission, Holland's aircraft was filmed crossing one ridgeline about 30 feet (10 m) above the ground. Fearing for their safety, the photography crew ceased filming and took cover as Holland's aircraft again passed low over the ground, this time estimated as clearing the ridgeline by only three feet (1 m). The co-pilot on Holland's aircraft testified that he grabbed the controls to prevent Holland from flying the aircraft into the ridge while the aircraft's other two aircrew members repeatedly screamed at Holland, "Climb! Climb!" Holland responded by laughing and calling one of the crew members "a pussy".
 
After that mission, the crew decided that they would never again fly with Holland and reported the incident to the bomb squadron leadership. The squadron commander, Lieutenant Colonel Mark McGeehan, reported the incident to Pellerin and recommended that Holland be removed from flying duty. Pellerin consulted with Holland and gave him a verbal reprimand and warning not to repeat the behavior, but refused to take him off flying duty. Pellerin also did not document the incident or the reprimand or notify his superiors, who remained unaware of the incident. McGeehan then decided that in order to protect his aircrews, he (McGeehan) would be the co-pilot on any future missions in which Holland was the command pilot. Evidence suggests that after this incident "considerable animosity" existed between Holland and McGeehan.