A Look Back at Steve Jobs' 2003 Stock Options Swap Reveals $10 Billion Opportunity Lost

153808 aapl growth since 2003

MarketWatch takes a look at "what might have been", examining Apple CEO Steve Jobs' decision to accept a March 2003 offer from the company to exchange his existing stock options for new ones at a more attractive price in comparison to the company's languishing stock price at that time, a move that would appear to have cost Jobs $10 billion in net worth at today's prices.

After the bursting of the tech bubble in early 2000, the Nasdaq Composite had plunged nearly 80% from its peak. Companies had folded left and right. Those left were staggering. Apple had fared as badly as any. Its stock had plummeted from a peak of $36 all the way down to about $7. (All prices have been adjusted for a subsequent stock split.)

With Jobs holding multiple lots of stock options with exercise prices of $9.15 (15 million shares) and $21.80 (40 million shares), his stake in those options was worthless at that time beyond the potential for share price increases to push the options into positive territory in the future.

Jobs was not the only Apple employee in that position, however, and when the company offered employees the opportunity to cancel their existing options in exchange for a significantly smaller number of options at a lower price, Jobs and others took the offer.

He volunteered to cancel all his options in return for a far smaller number of shares, worth about $75 million at the time. The trade made sense -- unless Apple boomed again.

Ahem.

The shares Jobs received are worth $2.5 billion at today's stratospheric prices.

Had Jobs held onto his original options, he would have seen them become profitable approximately a year and a half later and be worth $12.8 billion today. The difference means a missed opportunity of $10.3 billion for Jobs.

As the report notes, however, Jobs is of course not hurting for wealth, having been ranked the world's 136th richest person in Forbes' recent rankings. But the majority of Jobs' wealth comes from his holdings of Disney, where he became the company's largest individual shareholder after it purchased Pixar in 2006.

And there may have been another upside to Jobs' cancellation of his original stock options. A portion of those options, along with additional grants made to other Apple executives, was the focus of a backdating scandal, which resulted in an investigation by the U.S. Securities and Exchange Commission and the departure of former Chief Financial Officer Fred Anderson from Apple's Board of Directors and General Counsel Nancy Heinen from the company.

Related Stories

studio buds family

Beats Studio Buds Debuting Today With Active Noise Cancellation, Stemless Design, and More for $150

Monday June 14, 2021 8:00 am PDT by
We've seen a lot of teasers about the Beats Studio Buds over the past month since they first showed up in Apple's beta software updates, and today they're finally official. The Beats Studio Buds are available to order today in red, white, and black ahead of a June 24 ship date, and they're priced at $149.99. The Studio Buds are the first Beats-branded earbuds to truly compete with AirPods...
airtag in hand

Apple Enhancing AirTags Anti-Stalking Measures With Android App and Shorter Sound Intervals

Thursday June 3, 2021 11:10 am PDT by
Apple is enhancing AirTags security to prevent stalking using the Bluetooth devices, Apple told CNET today. Apple is already sending out over-the-air updates to AirTags that will shorten the amount of time before an unknown AirTag alerts you if it is in your possession. At the current time, AirTags play a sound after three days of being away from their owner. After the update, AirTags will...
maxresdefault

Here's How Apple's New iPhone to iPhone Data Migration Feature Works in iOS 12.4

Tuesday July 23, 2019 1:20 pm PDT by
Apple this week released iOS 12.4, the newest version of iOS 12 available for iPhones and iPads. One of the new features in iOS 12.4 is an updated data migration option that uses device to device transfers rather than relying on iCloud. Apple didn't provide much information on the new data migration feature, so we thought we'd check it out in our latest YouTube video. Subscribe to the ...
youtube apple tv

YouTube Discontinuing 3rd-Generation Apple TV App, AirPlay Still Available

Wednesday February 3, 2021 3:09 pm PST by
YouTube is planning to stop supporting its YouTube app on the third-generation Apple TV models, where YouTube has long been available as a channel option. A 9to5Mac reader received a message about the upcoming app discontinuation, which is set to take place in March.Starting early March, the YouTube app will no longer be available on Apple TV (3rd generation). You can still watch YouTube on...
macos catalina legacy system extension alert

Apple Begins Warning Users That 'Legacy System Extensions' Won't Work With a Future Version of macOS

Wednesday March 25, 2020 9:53 am PDT by
Apple has shared a new support document that indicates kernel extensions — which it calls "legacy system extensions" — will not be compatible with a future version of macOS because they "aren't as secure or reliable as modern alternatives."System extensions are a category of software that works in the background to extend the functionality of your Mac. Some apps install kernel extensions, which...
os x mountain lion macs 16x9 2

Apple Makes OS X Lion and Mountain Lion Free to Download

Wednesday June 30, 2021 12:19 pm PDT by
Apple recently dropped the $19.99 fee for OS X Lion and Mountain Lion, making the older Mac updates free to download, reports Macworld. Apple has kept OS X 10.7 Lion and OS X 10.8 Mountain Lion available for customers who have machines limited to the older software, but until recently, Apple was charging $19.99 to get download codes for the updates. As of last week, these updates no...
airtag precision finding

AirTag Includes U1 Chip for 'Precision Finding' Feature

Tuesday April 20, 2021 12:11 pm PDT by
Apple's long-awaited AirTag was finally unveiled today, and as expected, the small circle-shaped accessories can be attached to items like wallets, keys, and more to allow them to be tracked in the Find My app. As was rumored ahead of release, each AirTag is equipped with a U1 chip, and on devices that also have U1 chips, there's a Precision Finding feature. U1 Ultra Wideband chips are...
iOS 15 General Feature Yellow

Everything New in iOS 15 Beta 6: SharePlay Disabled, Safari Redesigned and More

Tuesday August 17, 2021 2:12 pm PDT by
Apple released the sixth beta of iOS 15 just a week after the fifth beta, but the new update brings some of the most significant tweaks that we've seen to iOS 15 during the beta testing period. Safari Redesign Apple in iOS 15 beta 6 has added a toggle to move the Safari address bar to the top of the interface, which returns Safari to an iOS 14-like design and mitigates all of the Safari...
m1 macbook air

Kuo: Mini-LED MacBook Air Coming in Mid-2022

Thursday July 22, 2021 7:48 pm PDT by
Apple will release a new version of the MacBook Air around the middle of 2022, Apple analyst Ming-Chi Kuo said today in note to investors seen by MacRumors. The upcoming MacBook Air will feature a 13.3-inch mini-LED display, which would make it the second Mac to gain mini-LED technology after the 2021 MacBook Pro, which is rumored to include a mini-LED display and is expected to launch later ...
2016 macbook pro flexgate b

Apple Faces Another Class-Action MacBook Pro ‘Flexgate’ Lawsuit

Thursday August 20, 2020 6:43 am PDT by
Another class-action complaint has been lodged against Apple, which claims that the company was aware of a MacBook Pro design flaw that caused some devices to have backlight display issues (via Apple Insider). The so-called "flexgate" problem was present in some MacBook Pro models manufactured between 2016 and 2017. The problem appears as dark patches along the bottom of the MacBook Pro's...