January 13, 2000: Steve Jobs’ longtime frenemy Bill Gates steps down from his role as Microsoft CEO, a month after his company’s stock hit its all-time high.
The news coincides with a turning point in the long-running battle between the two tech powerhouses. Microsoft begins a long decline from its previous dominance, while Apple continues its rise to the top.
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November 21, 1985: Following Steve Jobs’ departure, Apple comes close to signing its own death warrant by licensing the Macintosh’s look and feel to Microsoft.
The deal, between Microsoft co-founder Bill Gates and Apple CEO John Sculley, comes hot on the heels of the Windows operating system’s release. The pact gives Microsoft a “non-exclusive, worldwide, royalty-free, perpetual, nontransferable license to use [parts of the Mac technology] in present and future software programs, and to license them to and through third parties for use in their software programs.”
November 10, 1983: Microsoft tells the world about an upcoming product called Windows, which will bring the graphical user interface to IBM PCs. Although Microsoft’s announcement about the new operating system comes before Apple launches the Mac in 1984, Windows 1.0 won’t actually ship until November 1985, earning it a reputation as “vaporware.”
At the time, Apple doesn’t view Windows as much of a threat. That doesn’t take long to change, however.