“I sold pot and acid,” he says, laughing. “I didn't even really smoke yet, and I hadn't taken LSD yet, either. But my goal was to do the sound system, and I was pretty much willing to do almost anything short of horrible treachery to get it to happen. I don't really advocate that form of moneymaking, but it was a means to an end.”

Healy became obsessed with the Dead's sound. The LSD soon followed. Like the band, he had been seriously dedicated to his craft long before trying psychedelics, but the psychedelics pushed him further.

“I guess you would call it a hallucination or a dream or a bolt of lighting that hit me between the eyes or wherever,” he says. “But there was a moment when I flashed on what it was all supposed to sound like. And then it became a lifelong pursuit. I saw the whole, complete picture, the entire scope of exactly what it needed, what was missing. And so it was probably because of the psychedelics. Maybe LSD, maybe peyote, maybe mushrooms. It transformed it from a bunch of monkeys on typewriters to educated people making music.

“The dream was there, the model of sitting in your living room in front of the world's greatest stereo, smoking the fattest, biggest jay you can and listening to the most fabulous music over an incredible sound system, for each and every person at a concert. That was the model.”

A Deadhead bootleg parodying Maxell tapes’ “blown-away guy” ad campaign, 1980s. A bootleg for the Watkins Glen Summer Jam, depicting the Dead’s sound system, 1973.

A classic Dead shirt with the Ice Cream Kid, by Stanley Mouse and Alton Kelley, from the Europe ’72 tour. The tee for the band's spring 1984 tour, around the time they scrapped a studio album but continued building an audience on the road.

Healy's collection is loaded with sartorial souvenirs from moments that can be tough to remember. One unusually worn-out piece was imported from London and commemorates the conclusion of the arduous two-month-long trek across the Continent that would be featured on the Europe '72 live album. "I Heard the Grateful Dead at the Lyceum '72," the shirt reads, though Healy recalls nothing about the shows. “We were so stoned on acid at the Lyceum,” he says. Perhaps celebrating the tour's end, perhaps draining their acid vials over the four nights before heading home. “The duty at that point was probably trying to stay upright,” he says. One would hardly know: The Lyceum shows would yield half the music on the triple live LP.

Two different shirts represent the Watkins Glen Summer Jam, the July 1973 mega-concert with the Dead, the Allman Brothers, and the Band; an estimated 600,000 fans; and an on-site pirate radio station—the largest festival of the original festival era. One shirt is the official model; the other, an early Dead bootleg shirt, features a homemade hippie approximation of the band's already legendary P.A. “They were probably drawing the Hard Truckers [speaker cabinets],” Healy says fondly.

For Healy and his wife, Patti, the Watkins Glen International racetrack—the site of one of this year's competing “Woodstock 50th-anniversary” festivals—was a serious battlefield. Healy mixed sound for all three bands, a rare pleasure, in addition to presiding over the public sound check the day before. “But we were stuck at the soundboard for basically 36 hours,” Healy says. “There was nowhere to go. I stayed awake. It was such a screaming-meemies scene that I had to stay on top of it. There's another reality in that the ultimate responsibility for the audience rests on the sound system. If 600,000 people are there and help is needed and the sound system goes off, the whole thing can run amok and people can die. It's very, very serious.”

In the early '70s, when bands their size were buying private jets, palatial estates, or fancy yachts, the Dead poured their earnings into their sound system. Engineers like Healy (as well as roadies and others) were voting members at all-band meetings. With original Dead sound guru Owsley Stanley's mantra of “as above, so below,” they yearned to make literally equal sonic experiences for the band and the most distant audience member. The so-called Wall of Sound they developed was unsustainable. The era peaked with the band announcing its retirement from the road at the end of 1974. Of the stash in the boxes, Healy's lone surviving shirt from the year is utilitarian gray with no artwork at all, reading simply "1974 Tour".

The back of the tee for New Year’s at home at Bill Graham’s Winterland, 1977–1978. The front of the tee for the New Year’s at Winterland show, 1977–1978.

A bootleg replacing Dirty Harry’s weapon with the classic Deadhead taper mic setup, 1980s. The shirt from Cal Expo Amphitheater, Sacramento, 1986.

Several shirts and backstage passes, in startlingly unfaded shape, represent the Dead's appearance at Cornell University's Barton Hall in May 1977. A recording from that show routinely appears at the top of Deadhead favorites lists and was added to the Library of Congress's National Recording Registry—it finally received an official release in 2017. Healy remembers Cornell for the “computer freaks” that flocked to the soundboard.