From the archive: Otis Redding’s last flight

*Editor’s Note: This article is not updated from the original version that ran in the March 1983 issue of Madison Magazine. The archive article is being republished in tribute to the 50th anniversary of Otis Redding’s death.

Otis was a star now, and the cash was just pouring in. After a while, he didn’t have to run those Alabama roads anymore; he had his own airplane and a pilot to take him from place to place. The plane was a twin-engine job, and Otis was learning to fly it. Whether he was at the controls on December 10, 1967, on a flight from Cleveland to Madison, Wisconsin, no one ever knew. It didn’t much matter, because the plane didn’t make it.

-Robert Sam Anson, “Will Phil Walden Rise Again?”

Phil Walden was in Las Vegas, and he was on a roll. It had nothing to do with dice or cards, and very little to do with luck. By late 1967 Walden was rolling red-hot as a manager in the big bucks world of rock ‘n’ roll music, so it unusual, on December 10, to find him at a music convention in Las Vegas discussing which acts were hot and which were not and which one might be number one with a bullet.

Walden’s hottest act was someone Time magazine had called “one of the better exponents of that exhilarating American blend of the blues, gospel and pop: soul music.”

Walden had found the kid in his native city of Macon, Georgia. A tall black kid named Rockhouse was shaking the walls at segregated clubs around Macon, and one night Walden took him aside and told him how much he liked his act. The kid told Walden his real name, and Walden told Otis Redding he would make him a star. Walden was a hustler, and Redding could play music for real–the partnership clicked.

By 1967, Walden had under him dozens of acts. Otis Redding was still the biggest. He had just been voted number one male singer in Britain and a yet-to be-released single, “Dock Of The Bay,” had smash-hit written all over it.

In the late afternoon of December 10 1967, Phil Walden received a telephone call downstairs in his Las Vegas hotel. It was his brother Alan.

“Otis’ plane has gone down,” Alan said. “They’re still looking for him, but it doesn’t look good.”

Stunned, Phil Walden got in an elevator to go up to his room. A disc jockey who was attending the convention recognized Walden in the elevator and asked him a question.

“Say, what are you and Otis going to do with all that loot you’re getting?”

By the next morning, the world would know the tragic truth. Otis Redding, 26, had died in a plane crash in Lake Monona in Madison, where he had been scheduled to perform the night of December 10 at a Gorham Street club called The Factory.

In the 15 years that have passed since the tragedy, rumors have persisted about the crash and its aftermath, stories as hazy as the weather that raw December. Were drugs found on board the plane? What about the big sums of cash Redding supposedly always carried? Was the pilot qualified, or, as Robert Sam Anson intimated in an Esquire article on Walden, had Redding himself taken the controls?

Records from the National Transportation Safety Board were destroyed in 1977, according to Betty Scott of the NTSB’s Washington, D.C. office. But Madison Magazine recently obtained a copy of the official Madison Police Department report, a report which clears most if not all of the mystery surrounding the crash.

Redding and his band, the Bar-Kays had left Nashville, Tennessee, at about 1 a.m. on Saturday, December 9, in a twin-engine Beechcraft airplane piloted by commercial pilot Richard Fraser.

They flew to Cleveland, where they played three shows Saturday night. At 12:30 Sunday afternoon, the group departed Hopkins Field in Cleveland on a scheduled non-stop flight to Madison. There were eight people on board. The weather in Cleveland was overcast with good visibility: the weather in Madison was appreciably worse, with drizzle and thickening fog.

When the airplane was 10 miles south of the Madison airport, flight control was transferred from Chicago Federal Aviation Control to Madison. When the plane was four miles south of the airport above Squaw Bay (less than a mile from the crash site), it was given clearance to land.

FAA official Robert Kinn said later, “There was no indication of trouble from the plane.” Contact was lost at 3:25 p.m.

One of the Bar-Kays, Ben Cauley, 20, was the only one on board to survive the crash. According to the police report:

“While enroute to Madison, Cauley fell asleep and was suddenly awakened and experienced the sensation that the aircraft was in a spin and falling. He stated that things happened so fast, and that the plane was losing altitude at such a rapid rate, he found it difficult to breathe. He immediately unfastened his seatbelt, and grabbed an object, possibly some kind of cushion, and the aircraft plunged into the lake. He assumes the aircraft broke apart, as he found himself free of the wreckage in the water, and still clinging to whatever object he had grabbed. He heard Ronnie Caldwell (another of the Bar-Kays) calling for help, and started towards Caldwell to aid him; however Caldwell disappeared before he could make contact. He also heard Carl Cunningham (a Bar-Kay) calling for help, but stated Cunningham was too far away and he too disappeared. Within a few minutes, the police boat arrived and he was rescued.”

The plane went down about one-half mile out from the 4600 block of Tonyawatha Trail in Monona Village. Bernard Reese, who lived on that street, was outside at the time and told police:

“I heard a twin-engine plane overhead in the fog–I noticed that it was having engine trouble as there seemed to be a lack of power in the motors. The aircraft then came out of the overcast and approached the water–the left wing was angled to the left and appeared to be dipping. The plane hit the water and I heard a loud noise like an explosion or auto accident. There was no fire and the plane rested on the surface for three to five minutes and then sank.”

From the archive: Otis Redding’s last flight

What caused the crash? Cauley told police that he overheard a mechanic in the Nashville airport say that the battery system was not at full power.

The pilot, Richard Fraser, 26, had received his “Multi-Engine Land” license ten months prior to the crash. Fraser was indeed piloting the plane; Otis Redding was sitting next to him, in the co-pilot’s seat.

Upon witnessing the crash, Bernard Reese called the police. At 3:28 p.m., four Madison police officers were dispatched to the Lake Monona Boat House. Sergeant Ted Mell filed a report:

“Upon arrival at the scene, we took the boat out onto the lake, proceeded to the southeast corner of the lake where we located numerous debris. A man (Ben Cauley) was found clinging to couch type seat. This subject was taken aboard our boat. We continued the search and another man (Richard Fraser) was found in the water. The subject was still in a single passenger type seat and his seatbelt was still fastened. He was taken aboard the boat and I immediately began mouth-to-mouth resuscitation and closed heart massage. The other officers continued to search and another subject (Jimmie King, a Bar-Kay) was found still secured to a single passenger type seat by his seatbelt. We were unable to locate anyone else at this time and took boat to the Monona boat house. The three above persons were then conveyed to the hospital”

While the Madison police officers went back to the boat house, a Monona Village officer, John Pentleton, arrived at the crash scene in a boat with witnesses Bernard Reese and Christopher Dickert.

From Mell’s report: “They located no other survivors; however, they did pick up a small dark gray attache case.”

That attache case would become an object of much speculation. What did it contain? There was speculation at the time that it contained opium and marijuana. There were, however, no references to opium in official reports. References to marijuana are deleted from the official police report-crossed out with heavy black lines. From Detective Ralin Phillips’ report:

“In checking the attache case that was the property of Carl Cunningham (a Bar-Kay) I found 11 cigarettes ——— Those 11 items were placed under property tag #6308. The ——— were in a small metal cuff link box. The ——— were wet and were placed in my own locker to dry out.”

A police source today says the marijuana was deleted from the official report “out of consideration for the families of the victims.” Possession of marijuana in 1967 was a felony. As for the opium, Ted Mell, today a detective with the Madison police, says, “To be frank with you, I don’t even remember any attache case. I don’t remember anything at all about any opium.”

Memory serves a Monona Village officer, Lt. William Diebold, a little better.

“Do you want something for the record on that attache case?” he said recently. “You won’t get it.

When asked if controlled substances were found in the case, Diebold chuckled. “You mean something you don’t find in salad dressing?” he said. “I won’t say. We worked with the city on that.”

When darkness descended, further searching was called off. At The Factory, on Gorham Street, fans waiting to hear Otis Redding and the Bar-Kays were getting restless. That night they would hear only the scheduled warm-up band, named, in a gruesome bit of irony, the Grim Reapers. (Not long after the crash, the Grim Reapers changed their name, and are now known all over the world as Cheap Trick.)

At nine o’clock on the morning of December 11, police picked up the search. They had left buoys the previous night.

From Ralin Phillips’ report:

“Approximately 100 ft. North of the Easternmost buoy we found oil coming to the top of the water. We proceeded to drag the area and as we crossed the area the oil was slick and the drag hooks hooked onto something at the bottom. We measured the depth of the water at this location and found it to be between 45-60 feet . . . On (several divers) initial entry into the water they reported back that our grappling hook hooked on-to the fuselage of the plane. They reported the main body of the plane was almost beneath our boat and that it appeared to be in a twisted manner. On their second entry into the water (the divers) recovered the bodies of Otis Redding and Matthew Kelly (a Bar-Key). A rope was tied to Redding and when he was pulled to the surface it was found that he was still strapped to his seat. He also was wearing earphones. The officers stated that Redding’s body was located outside of the plane and Kelly’s body was recovered still within the body of the airplane itself. When they first saw the body of Kelly only his hand was visible. These two bodies were placed in the old police launch and conveyed to the Dane County Morgue.”

At the morgue, police were met Twiggs Lyndon, a booking manager for “Phil Walden Artists.” Lyndon told them he had flown in from Macon that day with Zelma Redding, Otis’ wife. Zelma would later become upset upon learning large amounts of cash she said her husband always carried were not present–and that some luggage had been tampered with.

From Ralin Phillips’ report:

“I went to the County Morgue and examined the bodies of Redding and Kelly. There was a head wound on Redding, right between his eyes, plus several other cuts around his face and neck. The right leg was also broken. The body of Kelly did not appear to be injured other than a bruised left eye and forehead. Coroner Chamberlain stated he was going to list their death as a result of internal injuries and drowning. A search of the body of Redding produced one Bulova watch, one black leather billfold and $302 in cash. I also removed a package of a substance similar to ——— (marijuana) that was wrapped in ——— from the right inside pocket of Redding. This will be analyzed to determine if it is ——— or not.”

The next day, December 12, Phillips returned to the crash site with a team of divers. The body of Carl Cunningham was found that day, as were a number of suitcases and other personal property of the victims.

On December 13, Phillips took the parts of the plane that were stored in the morgue and the Monona boat house to Truax Field and turned them over to Noel Lawson, an investigator for the Civil Aeronautics Bureau. He accompanied Lawson to Building #202 at Truax where some personal property of the victims was stored. From Phillips’ report:

“Mr. Lawson was quite disturbed when he showed me this luggage because it appeared as if someone had searched through it and it was not in the original position that he had left it. I later checked at the Station and was informed that officers had been dispatched to this building to search this luggage for the money that Mrs. Redding had reported her deceased husband had been carrying.”

Indeed, Redding was notorious for carrying large sums of cash. There was even a story that when he bought the Beechcraft, he was told the price was $100,000. Redding reportedly snapped open a briefcase and bought the plane with cash.

On December 14, four payroll checks made out to Otis Redding were found. They totaled $2,706.25. No great sums of cash were ever found, or at least reported.

On December 20, the body of Ronnie Caldwell was found by divers in the general area of the plane crash site. Other personal property belonging to the band was discovered. The body of Bar-Kay member Phalon Jones was not.

From the archive: Otis Redding’s last flight

In January of 1968, Phil Walden and Twiggs Lyndon released “Dock Of The Bay.” The lyrics, and Redding’s voice were haunting.

“Left my home in Georgia; headed for the Frisco Bay. I have nothing to live for; looks like nothin’ gonna come my way. So I’m just gonna set on the dock of the bay; watch the tide roll away.”

-Dock of the Bay, sung by Otis Redding

“Dock Of The Bay” was #1 on the Billboard Hot 100 chart for several weeks running, and by April had sold 1,400,000 copies.

But Phil Walden was personally devastated by Redding’s death, and only a few years later, another of his top stars, Duane Allman, died in a motorcycle accident. In 1980, Phil Walden’s Capricorn Records declared bankruptcy, with debts of more than $10 million.

Twiggs Lyndon, who had come to Madison with Otis’ wife, stabbed a man and went to prison. He got out, but in 1980 he went skydiving and didn’t bother to pull the ripcord. Friends say he feared growing old.

Otis Redding never had to worry about that, having died in the icy waters of Lake Monona at the age of 26. Back in Macon, they named a bridge after him.

Doug Moe was a regular contributor to Madison Magazine in March 1983. Moe went on to be editor of Madison Magazine. He currently writes a monthly column in the magazine as well as a weekly blog on madisonmagazine.com.

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Doug Moe is Madison Magazine’s award-winning columnist, long-time contributing writer and former editor. He writes Madison Magazine’s monthly print column and semi-weekly award-winning blog, both called Doug Moe’s Madison. He has also written numerous critically-acclaimed nonfiction books and thousands of newspaper columns and magazine articles over the past 40 years.