Weather, another constant foe of aircrews, once again put a damper on Fifth Air Force’s plans to attack Simpson Harbor on October 26, 1943 and then again on the 29th. Everyone was on edge. The Third Marine Division was slated to invade the beaches of Bougainville on November 1st, covered by a strike from the air. With the weather still not letting up, the Marines’ plan went on as scheduled without the strike. After days of waiting, the weather finally cleared up on November 2nd.
This raid would target the shipping in the harbor instead of Rabaul itself. 57 P-38s and 75 B-25s (covered by other P-38s) were sent out to take out the harbor’s shoreline defenses and drop “Kenney’s Cocktails” (phosphorus bombs) to hinder the enemy’s view of the attack, then hit all the shipping possible. There were hundreds of guns on the shore to protect the harbor. When members of the 3rd Bomb Group’s 13th Squadron attended the briefing for the mission, Richard Walker remembers it being a “very somber affair.” Realizing the type of defenses that they would be facing, it “was pretty much a prediction that all of us would not be coming home.” The crews sat “gray faced and quiet…”
Nevertheless, the men got in their planes and flew off to Simpson Harbor. Soon, the harbor was complete chaos. Smoke from the 345th’s phosphorus bombs unexpectedly rose at least 400 feet high, obscuring the the view for the 38th crews, who also discovered that some of the ships had moved and decreased the target area. On the approach to the harbor, the 13th and 8th Squadrons ended up going off course, which went against the original attack plan. Maj, Raymond H. Wilkins was leading the 8th Squadron and realized this mistake too late. He quickly tried to let the 13th Squadron’s leader know, then broke off and tried to get the 8th back to their original attack angle of 225 degrees.
The Japanese were ready by the time the 8th Squadron entered the harbor, as the 3rd Bomb Group’s 90th Squadron had left shortly beforehand. In the center of the harbor and at the far left of the formation, Wilkins made a sharp vertical banking right turn to attack a destroyer. This move left his B-25 completely vulnerable to gunfire, which badly damaged his plane during his attack. Wilkins skipped a bomb into the destroyer, then attacked a transport with a second bomb. Afterwards, he saw that only a cruiser remained before the harbor could be cleared. He strafed the cruiser to draw attention away from the other B-25s following him, and, in the process, exposed his plane again to antiaircraft fire. The left wing of his plane was hit, then crumpled, sending the aircraft into the water.
For his heroic actions, Maj. Wilkins was posthumously awarded the Medal of Honor. He and his crew became part of the 45 men that were lost that day, which would come to be known as “Bloody Tuesday.”