In 1990, John Chovanec’s mother married Steve Jobs’ father, Paul. Chovanec was never close to his stepbrother, who was then CEO of Pixar and Next, but their interactions were always amiable. On one memorable occasion, Jobs took Chovanec into his childhood bedroom—in the house with the famed garage where the first Apple computers were assembled—and fired up an early Macintosh to deliver a personal chronicle of how it was developed.

Now Chovanec, who wound up in possession of much of the contents of that bedroom, has consigned a collection of the ephemera to RR Auction for sale. Items include Jobs’ desk, its drawers filled with Reed College notebooks and work he did for Atari in the mid-’70s; the Bob Dylan 8-track tapes (and one Joan Baez tape) he listened to incessantly; a set of magazines that Jobs’ father kept to commemorate cover stories about his son; Jobs’ annotated horoscope generated by an Atari computer; his copy of How to Keep Your Volkswagen Alive; an early Apple poster that hung in the living room of the house; and a dozen bow ties that he wore in high school. Also up for bid: a document Jobs signed related to the sale of his father’s 1984 Ford Ranger pickup.

The Chovanec contributions are part of a larger collection of items up for bid. The star of the auction is the first check cut by Apple Computer Inc. (The auction house is not revealing the current owner.) Written on March 16, 1976, it predates the partnership agreement that formalized the company’s origin 18 days later. Cosigned by Jobs and Steve Wozniak, the $500 check is written to circuit-board designer Howard Cantin, who did the work for what would become the Apple 1. In a 2012 interview, Cantin said that Jobs actually offered him stock but he preferred a direct payment. So the cofounders paid him through a newly created Wells Fargo bank account with funds that came from the sale of Jobs’ VW bus and Woz’s HP calculator. Now, of course, the company is worth trillions of dollars. Previously, the earliest Apple check up for sale was #2, written on March 19, 1976, to Ramlor Inc., a circuit-board maker. In an August 2023 auction, it sold for $135,261. RR expects a much higher bid for this one—closer to $500,000.

Coincidentally, that original partnership agreement between Jobs, Wozniak, and Ronald Wayne, signed on April 1, 1976, is also up for bid this month at Christie’s. (Wayne got cold feet shortly after the signing and sold his 10 percent stake to the Steves for $800.) It’s among the “works of art, furniture and documents that changed American history” offered in a sale called “We the People: America at 250.” Christie’s estimates that the partnership document will sell in the range of $2 million to $4 million.

Items relating to early Apple history, especially items that involve Jobs, have gone to stratospheric prices in recent years. Jobs was famously reluctant to sign items, and his signature is regarded as among the most valuable of any public figure. Even a signed business card can go for as much as six figures. “There’s an emotional connection between Steve Jobs and collectors,” says RR’s executive vice president, Bobby Livingston. “People who start their own internet or engineering companies love Apple products.” Lonnie Mimms, the owner of check #2 and the founder of a tech museum in Roswell, Georgia, gushes about the value of such pieces of paper. “You can get anything in the world with a Steve Wozniak signature on it, but Jobs is another story. And the two of them together is the highest form of rarity.”

The items released by Chovanec are in another domain. Some of them seem to belong less to history than the realm of religious relics. After Paul Jobs died, Steve promised that Chovanec’s mother could live in the house “until you drop.” Chovanec says that the notoriously unsentimental Jobs wasn’t interested in anything in his former home except some family photos. When it came to the desk and its contents, he says Jobs told him to just take it. Chovanec’s mother, Marilyn, remained in the house until her death in 2019. For years the desk and other items were stored in Chovanec’s garage. He actually worked for Apple beginning in 2005, not revealing it to Jobs until after he was hired. During his 16-year stint at the company, first in the supply chain section and then in the retail group, few knew that he was Jobs’ stepbrother. “I felt it was nobody’s business,” he says. When Chovanec attended Jobs’ memorial service at Stanford in 2011, he says, “some executives looked at me with a look, like, ‘What are you doing here?’”

I asked Chovanec if he might be squeamish about offering some of the more personal items, like the bow ties and 8-track tapes. “I’m not queasy about this,” he says, noting that an earlier auction included a bomber jacket that Jobs was once photographed in. “Steve didn’t want any of this stuff,” he says. “My kids didn’t want anything. It’s just sitting here gathering dust and I want other people to enjoy it. It’s the 50th anniversary of Apple, and there are collectors out there who would really appreciate those types of things.” Chovanec says he is not currently in touch with the Steve Jobs Archive or Jobs’ wife, Laurene Powell Jobs, who he has not seen since the memorial service.

As to the provenance of check #1, we know that it did not come from cosigner Steve Wozniak. In an email, Woz says that he has very little Apple memorabilia. “I often think of some incredible things I had, but mostly they disappeared,” he says. He says that he did have extensive documentation of his development work arranged chronologically in 50 numbered manila folders, but he handed them over to lawyers representing Apple in an early copyright suit and never saw them again. “Bummer,” he says. “But the important notes are memories in my head.” Those memories may be priceless, but the actual Apple ephemera will come with a hefty price tag, to be determined at auction. No word yet if the 8-tracks still play.