An odd San Francisco evening in Jim Irsay’s touring man cave

Jim Irsay appeared out of thin air.

Through a cracked-open side entrance at San Francisco’s Bill Graham Civic Auditorium, I saw a police escort pull up, followed by an expensive-looking RV that might house a billionaire who sometimes cosplays as a rock star. A few camerapeople opened the door wider, presumably hoping to get a shot of the man of the hour. A few minutes passed, and Irsay’s handpicked ragtag band of rock-and-roll legends, including R.E.M.’s Mike Mills, Heart’s Ann Wilson and 86-year-old Buddy Guy — plus Indianapolis Colts great Edgerrin James — meandered to the nearby designated press conference area. 

And then poof — Irsay was on stage, like he’d done a Gob Bluth-style illusion. Did he come through the side door or somewhere else? I have no idea.

“I know my mind is sometimes hard to follow,” Irsay began, leaning hard on the podium. “I have trouble following it too, but if you just take a shot of Patron and settle in, I think you might understand what I’m about to talk about.”

I was already a drink deep. 

The stage area prior to the concert as part of the Jim Irsay Collection at Bill Graham Civic Auditorium in San Francisco, on Dec. 10, 2022.

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SantaCon ruled the daytime hours in the city on Saturday. The night belonged to SantaCon attendees’ spiritual, and literal, predecessors: late Gen Xers and boomers who love Bruce Springsteen and our Founding Fathers.

Irsay, the 63-year-old goateed owner of the Indianapolis Colts, provided a gathering space for his chosen people at Bill Graham, the eighth leg of the Jim Irsay Collection tour (prior stops include Chicago, Nashville and New York City). There’s no possible way to succinctly describe the range of artifacts on show. It’s a free-of-charge fever dream combining Irsay’s expensive taste in sports memorabilia, musical relics, timeless American literature and concerningly indispensable historical pieces (the only signed copy of the Atlantic Charter!), followed by a totally separate hour-and-a-half concert featuring Irsay on the vocals that will leave you saying, “Goddamn, Buddy Guy is still shredding.”

Muhammad Ali’s boxing robe on display as part of the Jim Irsay Collection at Bill Graham Civic Auditorium in San Francisco, on Dec. 10, 2022.

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Rocky Balboa’s boxing shoes on display as part of the Jim Irsay Collection at Bill Graham Civic Auditorium in San Francisco, California, on Dec. 10, 2022.

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Irsay has valued his collection, which he takes from city to city as a traveling personal museum of sorts, at roughly $100 million. That’s an impressive amount, until you consider Irsay’s net worth has ballooned to an estimated $3.4 billion, almost entirely via the always growing valuation of the Colts, whom Irsay inherited from his father Robert, an air-conditioning magnate. 

John Lennon’s glasses on display as part of the Jim Irsay Collection at Bill Graham Civic Auditorium in San Francisco, on Dec. 10, 2022.

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By the subterranean standards of NFL owners, the younger Irsay can be something of a breath of fresh air, if you filter it just right. A few months ago, at the league’s annual ownership meeting, Irsay tossed Worst Person Alive Dan Snyder under the bus, an obviously correct tactical move that no other owner had been willing to make. 

Irsay also frequently and openly discusses his past drug and alcohol addictions, and Saturday was no different as he ripped through cigarettes, cowboy hat on his head, while singing his favorite songs. Some people even find him endearing. 

“Maybe I’m a bit of a contrarian, but Jim himself, just the legend of Jim, I think he’s a lovable guy” is how Nick, a Colts fan and Indianapolis transplant, described him to me.

I could see it, if I squinted hard enough. His charm offensive honestly left me dumbfounded. Irsay’s name doesn’t crop up much in the parlor game of celebrities and billionaires potentially running for office, but why couldn’t he be a richer, more battle-scarred Matthew McConaughey?

Jim Irsay performs at the Jim Irsay Collection event at Bill Graham Civic Auditorium on December 10, 2022, in San Francisco. 

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Before the press conference, which Irsay was an hour late to — an outcome his PR team warned was inevitable — I checked out his collection of expensive s–t. There are clear pockets of interest for Irsay: bluesy white guys, beatniks, JFK and Abe Lincoln. Some of the items, like Jack Kerouac’s “On the Road” scroll, are visually impressive. Others, like the pricey U.S. bank notes he had on display, were hilariously out of place. Here is a broadside of Edwin Stanton’s telegram announcing President Lincoln is dead. And here is a rare $2 bill. Here is Harry Truman’s top hat from his inauguration. Here is a rare Topps card.

President Harry Truman’s top hat worn during his inauguration, on display as part of the Jim Irsay Collection at Bill Graham Civic Auditorium in San Francisco, on Dec. 10, 2022.

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Edwin Stanton’s telegram that Abe Lincoln was shot and killed, on display as part of the Jim Irsay Collection at Bill Graham Civic Auditorium in San Francisco, on Dec. 10, 2022.

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I made it back to the press conference room with plenty of time to spare. Irsay apparated and captivated his audience. “When Bob Dylan came in and wrote ‘Like a Rolling Stone,’ it was basically to England, telling them, how does it feel, you know, you tyrannical sons of bitches?’” Irsay said early on. 

The rest of Irsay’s speech garnered multiple applause breaks, including from the media members in the row in front of me, one of whom was legitimately moved by what she was hearing and kept throwing her pointer finger up in the air like she was hearing a church sermon. Her preacher was Irsay, doing a line-by-line annotated reading of Bruce Springsteen’s “Born to Run.” Here’s a typical rumination: “To me, the song is so powerful when it talks about the soul and the spirit as the reasons that we exist. I talk about it all the time: Being up here, spiritually, and I think it’s really important, what we do, we do together. And what we do, we have to do with individual courage as well, to support each other. Because in the end, it’s about that feeling of a higher power of that love, of the bigger love. And that’s what brings us together and keeps us together and keeps us sane. But there’s a lot of insane people on the streets today. And I look at it as all of our responsibilities.” 

After the press conference, I wandered around the venue. The line to see Irsay’s collection was ridiculously long. The upper bowls of the auditorium were pretty full. Since Irsay was late to his press conference, the concert was delayed too. I made my way to the ground floor of the auditorium, jotting down some notes about our future president, when a man in his 50s or 60s approached me and pointed at my media pass. “That looks like a liquor pass to me. They’re only serving beer and wine out here,” he said, gesturing to the auditorium. Another boomer putting on a charm offensive. I went to the VIP area and got him some tequila on the rocks, per his request. He asked me what I was going to write about and made it clear he hoped this would be a complimentary piece, because Mr. Irsay is a generous and good man. 

Guitars formerly owned by famous musicians on display as part of the Jim Irsay Collection at Bill Graham Civic Auditorium in San Francisco, on Dec. 10, 2022.

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Around 8:40 p.m., the lights dimmed, and the show began. A spotlight shined on Irsay, seated in the middle of the stage, who fittingly led off with a slowed-down “Born to Run,” minus the tangents. Next was Irsay’s own rendition of Warren Zevon’s “Lawyers, Guns and Money,” a song that seemed to have some personal meaning. He then wisely ceded the stage for a while to his assorted musician friends. Wilson, 72, performed a moving tribute to the late Christine McVie; later on, Buddy Guy put on an entrancing show. Other big names made appearances too, including John Fogerty of Creedence Clearwater Revival. Once again, the person who commanded the most attention was Irsay, who led an intermission of sorts where former Colts players tossed footballs into the crowd. When that was done, Irsay delivered another incomprehensible speech about drug addiction that nevertheless seemed to register hard with the crowd. 

Legendary musician Buddy Guy performing during the Jim Irsay Collection at Bill Graham Civic Auditorium in San Francisco, on Dec. 10, 2022.

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“If you’re on molly, it’s OK by me,” he joked to the crowd at one point, attempting to contrast responsible recreational drug use, which he condones, with drug addiction, which requires an intervention. He transitioned from that riff by singing “Hurt,” the Nine Inch Nails song covered by Johnny Cash. It wasn’t bad. I was admittedly distracted by the older man standing in front of me, wearing a feather cap, who had successfully wooed a fellow attendee he had met a few songs earlier. They swayed back and forth when Wilson came back on to sing Led Zeppelin’s “Immigrant Song.” A couple of older Deadheads were laying on the floor with their shoes off, soaking in the vibes. 

The Jim Irsay Collection concert at Bill Graham Civic Auditorium in San Francisco, on Dec. 10, 2022.

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I left the show toward the end, maybe a few minutes early. It was a damp, cold evening in San Francisco. On the Muni bus back, I revisited another part of Irsay’s stream-of-consciousness press conference.

“I think that we have a responsibility in this country to give back what we’ve earned,” the billionaire who inherited a pro football team said to an adoring audience. “… At this point in my life, I try to be of service. It’s not being noble or because I want to be a saint; it’s because, you know, when I see a human being suffering, it gets to me.” 

The salt-of-the-earth routine seems earnest. Who knows, maybe that’s enough to take the Jim Irsay Experience into prime time. I had a nice night at Bill Graham, and I found Irsay to be disarming and fascinating. He’s had eminently relatable personal struggles. He’s certainly not hateable in the Bay Area like, say, Elon Musk.

On Saturday, Irsay acknowledged that he’s wealthy enough to hypothetically “spend $1,000 a day since Jesus Christ was born” and not run out of money. (Jim had clearly broken out the calculator for that one, as by my calculations, it would take until 2739 to run up a billion-dollar tab that way.) His broader point was that other billionaires aren’t doing enough to give back, and he’s different — hell, he’s blessing you with the contents of his very expensive man cave. 

I’m not so sure he took the right message from “Like a Rolling Stone,” though. The tyrannical England interpretation is novel, but parts of the song are straightforwardly about the ultra rich fetishizing the rest of us. “You never turned around to see the frowns / On the jugglers and the clowns when they all did tricks for you / Never understood that it ain’t no good / You shouldn’t let other people get your kicks for you.”

Irsay might want to listen to that verse again.

Editor’s note: This story was updated on Dec. 13 at 1:59 p.m. to note that Nine Inch Nails first released “Hurt,” which was later covered by Johnny Cash. We apologize to Nine Inch Nails for the error.