E-mails From 2003 Reveal Microsoft Caught 'Flat Footed' by iTunes Music Store Launch

Over the weekend, Groklaw discovered a couple of interesting e-mails sent by Microsoft executives Bill Gates and Jim Allchin to other members of the Microsoft executive team revealing that the company had been taken by surprise by Apple's launch of the iTunes Music Store in April 2003. The e-mails were made public as part of an antitrust suit brought against Microsoft in late 2006 for which Groklaw has been documenting the exhibits provided as evidence.

Gates' comments offered a candid assessment of the situation, expressing surprise at Apple CEO Steve Jobs' ability to strike distribution deals with music companies.

Steve Jobs ability to focus in on a few things that count, get people who get user interface right and market things as revolutionary are amazing things.

This time somehow he has applied his talents in getting a better Licensing deal than anyone else has gotten for music.

This is very strange to me. The music companies own operations offer a service that is truly unfriendly to the user and has been reviewed that way consistently.

Somehow they decide to give Apple the ability to do something pretty good.

In trying to understand how best to respond to Apple's move, Gates noted that Microsoft was caught "flat footed" by Apple's music download service and questioned appropriate strategies to respond.

I am not saying this strangeness means we messed up - at least if we did so did Real and Pressplay and Musicnet and basically everyone else.

Now that Jobs has done it we need to move fast to get something where the UI and Rights are as good.

I am not sure whether we should do this through one of these JVs [joint ventures] or not. I am not sure what the problems are.

However I think we need some plan to prove that even though Jobs has us a bit flat footed again we move quick and both match and do stuff better.

Microsoft vice president Jim Allchin offered a briefer assessment of the situation, offering only a pair of observations:

1. How did they get the music companies to go along?

2. We were smoked.

The same court case earlier revealed another e-mail from Allchin from 2004 in which he famously said that he "would buy a Mac today if I was not working at Microsoft." Steve Jobs used the quote to take a jab at Microsoft, displaying Allchin's statement at the beginning of Jobs' keynote at Macworld San Francisco 2007.

Related Forum: Mac Apps

Popular Stories

iphone 17 models

No iPhone 18 Launch This Year, Reports Suggest

Thursday January 1, 2026 8:43 am PST by
Apple is not expected to release a standard iPhone 18 model this year, according to a growing number of reports that suggest the company is planning a significant change to its long-standing annual iPhone launch cycle. Despite the immense success of the iPhone 17 in 2025, the iPhone 18 is not expected to arrive until the spring of 2027, leaving the iPhone 17 in the lineup as the latest...
duolingo ad live activity

Duolingo Used iPhone's Dynamic Island to Display Ads, Violating Apple Design Guidelines

Friday January 2, 2026 1:36 pm PST by
Language learning app Duolingo has apparently been using the iPhone's Live Activity feature to display ads on the Lock Screen and the Dynamic Island, which violates Apple's design guidelines. According to multiple reports on Reddit, the Duolingo app has been displaying an ad for a "Super offer," which is Duolingo's paid subscription option. Apple's guidelines for Live Activity state that...
Clicks Communicator Feature

'Clicks Communicator' Unveiled — Will You Carry This With Your iPhone?

Friday January 2, 2026 6:35 am PST by
The company behind the BlackBerry-like Clicks Keyboard accessory for the iPhone today unveiled a new Android 16 smartphone called the Clicks Communicator. The purpose-built device is designed to be used as a second phone alongside your iPhone, with the intended focus being communication over content consumption. It runs a custom Android launcher that offers a curated selection of messaging...
Low Cost MacBook Feature A18 Pro

Low-Price 12.9-Inch MacBook With A18 Pro Chip Reportedly Launching Early This Year

Friday January 2, 2026 9:08 am PST by
Apple plans to introduce a 12.9-inch MacBook in spring 2026, according to TrendForce. In a press release this week, the Taiwanese research firm said this MacBook will be aimed at the entry-level to mid-range market, with "competitive pricing." TrendForce did not share any further details about this MacBook, but the information that it shared lines up with several rumors about a more...
Low Cost A18 Pro MacBook Feature Pink

Apple's 2026 Low-Cost A18 Pro MacBook: What We Know So Far

Friday January 2, 2026 4:33 pm PST by
Apple is planning to release a low-cost MacBook in 2026, which will apparently compete with more affordable Chromebooks and Windows PCs. Apple's most affordable Mac right now is the $999 MacBook Air, and the upcoming low-cost MacBook is expected to be cheaper. Here's what we know about the low-cost MacBook so far. Size Rumors suggest the low-cost MacBook will have a display that's around 13 ...
Apple Fitness Plus hero

Apple Announces New Fitness+ Workout Programs, Strava Challenge, and More

Friday January 2, 2026 6:43 am PST by
Apple today announced a number of updates to Apple Fitness+ and activity with the Apple Watch. The key announcements include: New Year limited-edition award: Users can win the award by closing all three Activity Rings for seven days in a row in January. "Quit Quitting" Strava challenge: Available in Strava throughout January, users who log 12 workouts anytime in the month will win an ...
Mac Pro Feature Blue

What's Happening With the Mac Pro?

Wednesday December 31, 2025 9:59 am PST by
Apple hasn't updated the Mac Pro since 2023, and according to recent rumors, there's no update coming in the near future. In fact, Apple might be finished with the Mac Pro. Bloomberg recently said that the Mac Pro is "on the back burner" and has been "largely written off" by Apple. Apple apparently views the more compact Mac Studio as the ideal high-end pro-level desktop, and it has almost...