Steve Jobs’s Infamous Leather Jacket and More Vintage Apple Memorabilia Could Be Yours

Apple aficionados can score clothing, computers, and even checks signed by the late tech tycoon.

A polaroid of Jobs and the founder's brown bomber jacket, both on offer, before the famous photo of him wearing it. Courtesy of RR Auctions

Most avid Apple collectors fondly remember an era where the tech giant was but a pithy underdog. Now, such fans have another chance to score—and even wear—a slice of that bygone moment, courtesy of an online sale by RR Auctions.

The house’s latest edition of “Steve Jobs and the Apple Computer Revolution” brings 278 more pieces of tech paraphernalia under the hammer, including the requisite cache of sealed first generation iPhones. One coveted 4GB specimen is slated to sell for nearly $16,000, though a similar example gaveled at $147,286 during their last Apple auction, in March. Over 200 lots in this sale center on Apple and its mythic co-founder Steve Jobs, but vintage video games and other tech ephemera are also on offer. Bidding starts closing on August 22.

Six lots featuring Jobs’ signature achieved staggering sums during the springtime event with RR Auctions. An autographed 1983 business card and a signed check dated to 1976, the year of Apple’s founding, both shattered their estimates by commanding almost $200,000.

A photograph of a Wells Fargo check from "Apple Computer" signed by "Steven Jobs" in 1976, depicted in a clear plastic cover on a white background

A signed check made out at the opening of Apple’s bank account, up for grabs in this month’s sale. Courtesy of RR Auctions

This month’s sale is more than twice as large as the house’s first. Several signed lots are already leading its expansive offerings, including a framed 5-year employee service award (estimated $10,000), two checks from 1976 (both estimated $25,000), and a handwritten note (estimated $8,000) that says “Hello 9th Grade!” According to its description, “The consignor notes that his father-in-law attended a conference where he met Jobs and asked him to sign for the high school class taught by his wife, a teacher in Hollis, NH.”

The current frontrunner, however, is a restored, fully-functional Apple-1 Computer (estimated $300,000). An extensive letter of provenance from Dana Reddington, Apple’s first applications engineer, details how Jobs and Steve Wozniak let him pick this motherboard from a pile submitted for Apple’s trade-up program in 1978. The computer’s existence was unknown to the collecting community prior to this sale. Fans who prefer contemporary computers can score Apple’s Lisa computer (estimated $75,000)—which was a flop in its day, but one of the first to feature a monitor. Both machines come with all the necessary accessories.

A photograph of an Apple-I computer board on a white background, with a small black and white photograph of two men on top of it

Dana Reddington’s Apple-I. Courtesy of RR Auctions

Speaking of which, a brown leather bomber that Jobs wore in a now-iconic photo flashing IBM the middle finger follows these two highlights with an estimate of $75,000. By comparison, Apple-branded knick knacks like a kite and playing cards could sell for $200 and $300 respectively.

Former Apple marketing employee Dennis Gobets contributed some gems, too. A rescued section of the company’s legendary Lake Donner hot air balloon from 1981—which appeared at Wozniak’s wedding—could sell for $10,000. A 1986 poster of Jobs’ scathing message to ad agency Chiat/Day, an archetypal relic of Apple history, bears a $10,000 estimate.

A photo of a rainbow Apple hot air balloon floating over a lake in front of a snowy mountain and blue skies

The Apple hot hair balloon in action. Courtesy of RR Auctions

But, if Apple’s bombast isn’t your brand, this sale’s got others store. Elon Musk appears in a signed photo commemorating Tesla’s IPO in 2010 (estimated $3,000), and Bill Gates’ Microsoft Corporate Campus access badge from 1994 is up for grabs thanks to a savvy former security employee from the company’s Redmond, WA headquarters.

The consistent growth of this category foreshadows more treasures like these surfacing in the years to come.

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