Al Di Meola Uses Jerry Garcia’s ‘Tiger’ Guitar For Grateful Dead Cover In Chicago

UPDATE (May 7, 2026 10:30 a.m. PT): Al Di Meola shared official video of his “Uncle John’s Band” performance with Josh Olken on YouTube. Watch the full version below.

Al Di Meola brought his 2026 tour to Park West in Chicago on Sunday (May 3), where he had the opportunity to play Jerry Garcia's iconic “Tiger” guitar. Di Meola had “Tiger” in hand when enlisted Terrapin Flyer guitarist Josh Olken for a duet on Grateful Dead favorite “Uncle John’s Band,” the penultimate song of the night.

“Tiger” came on loan to the jazz great from Family Guitars. The Chicago-based company’s Bobby Tseitlin purchased the guitar in March for $11.56 million at an auction in New York City. Family Guitars haven’t kept “Tiger” caged up as Derek Trucks played the axe during Tedeschi Trucks Band's Beacon Theatre residency shortly after the auction and then again two weeks later with Terrapin Flyer in Chicago.

Luthier Doug Irwin made the guitar for Jerry Garcia. “Tiger” was Garcia’s main instrumental from 1979 through 1989. Irwin, who died in March at age 76, spent roughly 2,000 hours crafting “Tiger” over a six-year span. Famed Garcia guitars Wolf, Rosebud, Eagle and Wolf Jr. were also built for Jerry by Doug Irwin.

Al Di Meola’s Grateful Dead fandom dates back to the late ’60s. “I never got to meet Jerry Garcia, but I later heard he mentioned me as one of his favorite guitar players. I couldn’t believe it, honestly,” Di Meola wrote on social media in a caption accompanying video of his recent “Uncle John’s Band” performance.

“When I was 15, my friends and I would skip school, take the bus into the city, and see the Grateful Dead at the Fillmore East. Some of my best memories! That era was magical!,” the guitarist added. “Last night in Chicago, I had the chance to play Jerry’s famous ‘Tiger’. It was emotional in a way I didn’t expect. This is a close-up from soundcheck, just getting a feel for it. And there it was… the Jerry tone.”

Al Di Meola debuted his version of “Uncle John’s Band” in January shortly after the death of Grateful Dead co-founding guitarist Bob Weir. He’d since the covered the song four more times before Sunday night as per Setlist.FM statistics.

Di Meola brought out Josh Olken from Chicago-based Grateful Dead tribute act Terrapin Flyer on Sunday. The pair delivered a magical version of “Uncle John’s Band.” Both guitarists traded solos on the instrumental cover.

Watch the official video of Al Di Meola and Josh Olken performing “Uncle John’s Band” and performing the song in concert below: