Soul finale

He had fallen asleep, and when he woke it was to chaos inside the small plane.

They were descending so rapidly that Ben Cauley struggled to breathe. He managed to unfasten his seatbelt, and grab a cushion. Then they hit, and he was loose in the water, terrified — he couldn’t swim. He clung to the cushion. The water was freezing. He heard a voice, a cry for help, then another. After that, nothing, until the police boat arrived.

They took him to the emergency room at Methodist Hospital. He was treated for cuts and scrapes on his face and head. It was only after he was put in Room 201 that a police officer walked in and told Cauley he was a lucky man.

“Why?”

“Because everybody else is dead.”

Among the seven others on board was a famous name — Otis Redding, 26, the plane’s owner, a soul singer on the brink of superstardom. Redding’s bravura performance at the Monterey Pop Festival six months earlier had electrified the music world.

Redding and his band, the Bar-Kays — Cauley played trumpet — were heading to Madison for two scheduled shows that night at The Factory, a club on West Gorham, near State Street.

Instead, their plane plunged into Lake Monona.

Fifty years later, Redding’s legacy lives on. Untimely deaths have a way of making legends, but it’s more than that. Part of it is that talent endures.

In 2010, Rolling Stone ranked Redding the eighth greatest singer of all time, noting his key tracks were “(Sittin’ on) The Dock of the Bay,” “These Arms of Mine” and “Try a Little Tenderness.” In 2011, the hip-hop artists Kanye West and Jay-Z recorded a song, “Otis,” that mixes in Redding’s rendition of “Try a Little Tenderness.” The video of the song has been viewed more than 135 million times.

On Dec 15, Rhino is releasing “Otis Redding: The Definitive Studio Album Collection,” a 7-LP set. That follows last year’s six-CD collection, “Otis Redding: Live at the Whiskey a Go Go.”

Hearing those live recordings last fall prompted Madison musician Kevin Willmott II to form and front a Redding tribute band, Don’t Mess with Cupid, named for a Redding song. The band plays the Majestic Theatre Dec. 7.

Willmott, 28, says he discovered Redding’s music after high school, when he was immersing himself in the music of such soul pioneers as Smokey Robinson and Donny Hathaway. Redding was a “mesmerizing” presence on stage, says Willmott: “He was just a fully rounded entertainer. He was having a great time and everyone else was having a great time.”

His music endures, says Willmott, because of its human emotion. “He really tapped into the soul of being in love and feeling pain and just trying to exist.”

Rain was falling in Cleveland when the twin-engine Beechcraft 18 took off for Madison in the early afternoon of Dec. 10, 1967.

On board were Redding, Cauley, the pilot, Richard Fraser, four other members of the Bar-Kays — Phalon Jones, Ronnie Caldwell, Carl Cunningham and Jimmy King — and a 17-year-old boy named Matthew Kelly, invited by the Bar-Kays to serve as Redding’s valet.

Redding was a Georgia native who was discovered and managed by the Southern R&B impresario Phil Walden, who later helped launch the Allman Brothers Band.

Walden was with Redding at Monterey in June 1967, when Otis soared. The manager was soon commanding a minimum of $3,000 a gig for Redding, who began traveling by private plane, first a leased Cessna, then the Beechcraft, which he bought used for $78,000.

The pilot, Fraser, was trained by Jim Lowe, who ran the charter plane operation at the airport in Macon, where Redding lived with his wife, Zelma.

At 3:25 p.m. on Dec. 10, 1967, Fraser communicated with Truax Field, the Madison airport. He was four miles south of the runway, and reported no problems. But an earlier communication with the tower had informed Fraser of a low ceiling and poor visibility in Madison, so the pilot set the controls on autopilot, preparing for an instrument landing.

“I heard an engine in distress,” Chris Dickert says.

Now 71, Dickert lives on a farm outside Evansville. Back then, he was a 21-year-old college student, living with his parents on Tonyawatha Trail in Monona. There was a football game on TV that afternoon. It was his mother’s birthday. She’s 94 this year.

Dickert walked from the living room to the dining room and peered out the window just in time to see a plane collide with the surface of the lake.

A neighbor a few houses down, Bernard Reese, president of Gardner Baking, was outside in his front yard.

“I heard a twin-engine plane overhead in the fog,” Reese, who died in 2005, later told police. “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 plane hit the water and I heard a loud noise like an explosion.”

The most detailed examination of the possible cause of the crash — the National Transportation Safety Board’s report was a single page saying “undetermined”—was done by Jonathan Gould, who published his findings in his terrific Redding biography, Otis Redding: An Unfinished Life, which came out earlier this year.

“I’m pretty obsessive,” Gould tells me, outlining how he’d tracked down and interviewed Henry Lowe, the son of Jim Lowe, the Macon airport pilot and instructor who’d counseled Redding when Otis first got interested in planes.

“When it happened,” Henry Lowe told Gould, “my dad felt he knew exactly what it was about.”

Jim Lowe was certain ice build-up on the airframe brought down the plane. The weather was right for it, and Fraser, a Southern pilot, had little experience in the conditions. Autopilot would hide the effects — until it didn’t, at which point the plane would plummet, in the manner witnessed by Reese.

“You can’t know these things for sure,” Gould says. “You try to come up with a plausible explanation based on people who know something about this stuff.”

In his book, Gould concludes with this: “Of the six other fatal accidents involving Beech 18s on final approach between 1967 and 1983, all of them involved icing conditions, and all but one of them took place in the Great Lakes region.”

After the plane hit the water, Dickert’s mother called police, as did Bernie Reese. Reese then went back outside, where he encountered Dickert, and the two of them ran to a nearby boat landing, where Reese’s son’s boat was trailered. As they were clearing a snow fence out of the way, a Monona police officer arrived. Soon they were all in the boat, headed for the crash site.

When they got there, a police boat was already on the scene. There was debris in the water, a wheel from the plane, but no signs of life.

Dickert recalls: “A police officer on the other boat said, ‘We have one survivor [Cauley]. We’re going to go back.’”

Later Sunday, divers would recover the bodies of Fraser and King. Redding’s body was found Monday, still strapped to the co-pilot’s seat, where he’d been sitting next to Fraser. Eventually, all the bodies were recovered.

Sunday afternoon, in the boat with Reese, Dickert reached out and brought aboard a dark gray attaché case that was floating on the surface. The case and its contents would become one of the enduring mysteries of the crash.

Ken Adamany booked Otis Redding at The Factory because James “Curley” Cooke, of the Steve Miller Band, told him he must. Cooke had been at Monterey, as had Madison’s White Trash Blues Band, who also raved to Adamany about Redding.

“Curley called after Monterey and said, ‘You’ve got to see this guy,’” says Adamany.

Adamany, who lives in the Madison area, still has a copy of the Redding contract.

In 1967, Adamany was a young promoter and club operator, and he hired UW-Madison sophomore William Barr, to create the poster for the show, which featured Redding and the Bar-Kays, and a warm-up band called The Grim Reapers, precursor of the Adamany-managed Cheap Trick.

“It [the poster] was meant to be an allegory of tenderness,” Barr told Isthmus in 2007.

The first Adamany knew that something was wrong came with a call late Sunday afternoon from the police.

“Were you expecting an orchestra?” the officer asked, explaining there had been a plane crash.

Redding’s agency had sent word that the group would be busing from Cleveland.

Adamany — thinking that Redding’s band hardly constituted an orchestra, and that they weren’t flying — directed the police elsewhere. But they called twice more, and the terrible truth emerged. Soon the police showed up at The Factory, and helped manage the crowd.

“We were all shocked,” Adamany says. “Everybody was running around. Phone calls began coming in from all over the country. It was hectic. Something you never want to experience.”

There was anger and disbelief among ticket buyers. Adamany quickly announced immediate refunds, and at the suggestion of the police, opened the doors for a free show. The Grim Reapers played, followed by a Milwaukee band, Lee Brown and The Cheaters, that Adamany had hastily recruited to round out the bill.

They got through the night. Adamany, dazed, thought about how excited The Factory staff was to bring Redding to Madison. The night would never truly leave him. “With all the shows we did after that,” Adamany says, “I was always wary [that something might happen]. It was always in the back of my mind.”

Adamany sent a note of condolence to Redding’s widow, and received a note in return. “Your generous expression of sympathy during our bereavement is deeply appreciated. There is no sorrow that Heaven cannot erase. May God bless you. Zelma Redding.”

Zelma came to Madison on Dec. 11, the day after the crash, with a man named Twiggs Lyndon, who worked for Phil Walden in Macon.

A front-page story in the Dec. 12 Wisconsin State Journal, detailing the events of Dec. 11 — the top headline was “Divers find Redding’s body” — contained this paragraph:

“The divers will also search for Redding’s briefcase which Twiggs Lyndon, a representative of his Macon booking agent, said is believed to contain about $4,000 in cash.”

Except the briefcase, or attaché case, had already been found, floating on the surface of the lake not long after the crash, by Chris Dickert.

“I specifically remember the initials O.R. on the case,” Dickert says. He had no idea at the time whose initials they were.

When he and Reese returned to the boat landing, there were a couple of Monona police cars waiting.

“I helped Bernie load the boat,” Dickert says. “A police officer took the case, and I specifically remember it sitting on the hood of a police car.”

A Madison police sergeant filed a report that references the search made by Reese and Dickert, after the first police boat departed the scene with the survivor, Ben Cauley.

“They located no other survivors,” the sergeant wrote, “however, they did pick up a small dark gray attaché case.”

Yet the case, and the money presumed inside, apparently never made it into an evidence locker; there is no further mention of it in the reports.

“The case was returned, but the money vanished without a trace,” Gould writes in his biography.

When I ask Gould about that, he says his source was “an unpublished interview with Phil Walden that dates from 1990. It’s certainly not definitive, and Phil’s account has more to do with his efforts to convince the coroner and the police to suppress the fact that a small amount of marijuana was found, either in the briefcase or on Otis’s body.”

Finally, adding still more confusion is a paragraph from a short, un-bylined article in the Wisconsin State Journal on Dec. 21— 11 days after the crash. Madison historian Stu Levitan found it while researching his book on 1960s Madison. It said this: “An estimated $3,000 to $4,000 in gate receipts that the troupe was believed to have been carrying was also recovered.”

The shattered aftermath of the crash brought forth a wonder: “(Sittin’ on) The Dock of the Bay” was released as a single in January.

Perhaps the best account of its recording is a 2013 interview given to the Wall Street Journal by Steve Cropper, who played with Booker T. and the MGs and was a producer at Stax Records in Memphis, where Otis had recorded since 1962.

In November 1967, Redding flew to Memphis, called Cropper from the airport, and said, “Crop, I’ve got a hit. I’m coming right over.”

Redding explained he’d written the song post-Monterey, having borrowed promoter Bill Graham’s houseboat in Sausalito.

Cropper wasn’t immediately impressed. “Otis,” he said, referencing an early lyric, “if a ship rolls in, it will take on water and sink.”

Redding wanted the line kept in; later, Cropper would see ferry boats roll on the waves in Sausalito and understand. It was Cropper who added the sounds of the sea and seagulls to the finished record.

They worked into December, then on Dec. 8, Redding had to leave for the concerts in Nashville, Cleveland and Madison. He saw Cropper at Stax.

“See ya on Monday,” Otis said.

A few months later, “(Sittin’ on) The Dock of the Bay” became the first posthumous #1 hit in Billboard magazine’s history.

Two pieces of the doomed airplane — one with “Otis” written on it, and another saying “Redding” — are in the Rock & Roll Hall of Fame in Cleveland.

But Redding had his name on both sides of the plane, and in 2004 I learned there was a piece of the plane with “Otis” written on it on display at the Hard Rock Café in Las Vegas.

At the same time, I learned who could tell me how it got there.

His name is Larry Goodman, although if you were around Madison in the 1970s, you would have known him as Charlie “Rock ‘n’ Roll” Simon, the 6-10 p.m. disc jockey on the immensely popular WISM/AM radio station, 1480 on the dial.

I reached him by phone in 2004 in San Diego, where he had been selling radio time at a station for two decades.

He was happy to tell me how he ended up with a piece of Otis Redding’s airplane.

“There was a local band, I won’t tell you which one,” Goodman said. “One night they went out to wherever the salvage team had put the pieces of Redding’s plane, and they sawed off the pieces with his name on them.”

A Madison blues guitarist once told me he’d had an “Otis” piece of the plane, but eventually decided it was “bad karma” and left it in his apartment when he moved out.

“That fits,” Goodman said, explaining that a Madison landlord came into possession of the plane piece. The man’s wife soon tired of having it in the house. “He asked if I wanted it,” Goodman said.

He did. Goodman took it with him to San Diego, but eventually Goodman traded it to the Hard Rock Café for a Hofner bass guitar signed by Paul McCartney.

More readily available — although still quite rare — are the original posters Adamany hired artist William Barr to create for the Redding show in Madison.

“My records show that we printed 100 — 50 of each color,” Adamany says. “One with a dark blue background and one with a yellow background.”

In 2006, one was sold on the internet auction site itsonlyrockandroll.com. The consignor was Gary Sohmers, who in the 1970s edited a Madison music guide and later appraised pop culture items for Antiques Roadshow on PBS.

In 1981, Sohmers’ music guide did a lengthy article on the Redding crash, and a Madison woman who had one of the original posters let him reproduce it for the article.

“Twenty-five years later,” Sohmers told me, “she saw me on television, and got in touch about selling the poster.”

The poster sold for $7,381.83.

There wasn’t room for everyone on the private plane from Cleveland to Madison that rainy afternoon 50 years ago. One of the Bar-Kays, James Alexander, and Carl Sims, a young singer Otis had invited along to open, flew commercial.

“I identified the bodies,” Alexander told me when we spoke in 2014.

It was the 50th anniversary of the founding of the Bar-Kays in 1964. Alexander and Ben Cauley — who died in 2015 — re-formed the band to honor their lost friends, Alexander said.

They played a series of shows in that anniversary year, and an online setlist from a performance at the Mahaffey Theater in St. Petersburg, Florida, that August shows the Bar-Kays played “Try a Little Tenderness” and “(Sittin’ on) The Dock of the Bay.”

The plane sank, the music still soars.

“I don’t think there’s another artist like him,” Adamany says of Redding. “I haven’t heard anything that approaches those early records. There was Wilson Pickett — some others like that — but they couldn’t approach Otis.”

Gould calls Redding “a touchstone for a lot of music listeners who might not have that strong a relationship with rhythm and blues.”

Kevin Willmott II will become Otis on stage at the Majestic with Don’t Mess with Cupid Dec. 7. “The 50th anniversary was our target,” he says. “We’ve had a year to get something really special together. My hope is to have it be kind of healing for people.”

I look forward to seeing Don’t Mess with Cupid perform. I first wrote about Otis Redding nearly 35 years ago — a long magazine story in 1983 — and I’ve revisited the crash and Redding’s sad but nevertheless real connection to Madison in columns and articles many times since. Hearing “(Sittin’on) The Dock of the Bay” can still give me chills. I doubt I’m alone. 

[Editor's note: A caption on the photo for the Factory was corrected to say that the space is now occupied by A Room of One's Own.]