People forget that Apple of today probably wouldn't be around if Microsoft hadn't given them $150M to save them from bankruptcy in 1997[1].

With the introduction of IE in 1995 and its deep integration into Win95 and ruthless take-no-prisoners assault on Netscape, Microsoft was probably already aware that they were starting to resemble a monopoly, given Apple's poor sales and market share at the time. My personal take is that MS propped up Apple to help appear to have a competitor ahead of the Antitrust action in 2001[2].

[1]https://www.cnbc.com/2017/08/29/steve-jobs-and-bill-gates-wh...

[2]https://en.wikipedia.org/wiki/United_States_v._Microsoft_Cor....