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Thomas Penfield Jackson — the federal judge who declared Microsoft a monopoly and ordered a breakup of the company— died this weekend at the age of 76 from complications of transitional cell cancer, according to a New York Times report.

Thomas Penfield Jackson

Jackson’s landmark breakup order, issued on June 7, 2000, was later overturned by an appeals court, after his colorful criticism of the company and Bill Gates in press interviews was found to be a sign of bias. That gave Microsoft the breathing room to reach a settlement in the case, and the company was able to remain intact.

Looking back at the breakup order today, it’s a reminder of just how much things change in the tech industry, and how quickly. Here’s the core of what Jackson ordered.

The separation of the Operating Systems Business from the Applications Business, and the transfer of the assets of one of them (the “Separated Business”) to a separate entity along with (a) all personnel, systems, and other tangible and intangible assets (including Intellectual Property) used to develop, produce, distribute, market, promote, sell, license and support the products and services of the Separated Business, and (b) such other assets as are necessary to operate the Separated Business as an independent and economically viable entity.

In the meantime, Microsoft and the industry at large have evolved into much more complex organisms. The rise of devices and cloud services makes the notion of separating the company into operating systems and applications seem almost quaint in retrospect.

More and more, Microsoft is aiming to tightly integrate its businesses and unite its various divisions. Breaking up the company these days would be much, much more complex.

But what would have happened if the breakup had gone forward in 2000? Given what we’ve seen, my hunch is that the two companies would have naturally evolved to be complete sets unto themselves — specializing in operating systems and applications, respectively, but gradually adding more and more capabilities until they were each alternative versions of each other. Sort of like a movie or book where you get to see two paths taken by the protagonist, branching out from a pivotal decision at a moment in time.

Would that have been a better outcome? In the Darwinian tech world, it’s quite possible that one of the “Microsofts” would have failed, or been acquired by another company, leaving a leaner Microsoft as the survivor.

But we’ll never know, thanks to a talkative federal judge. RIP, Thomas Penfield Jackson.

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