In December 2008, there was an emergency meeting at Microsoft that those present reportedly nicknamed the "cage match." Terry Myerson, a young executive with a blunt affect and a love of Hawaiian shirts, had just been promoted to head of mobile engineering. At the time, that meant Windows Mobile, the aging, touch-unfriendly mobile operating system that Microsoft first released in 2003.

Myerson called the meeting. On the table was a prototype of a new Windows Mobile phone. On everyone’s mind was Apple’s iPhone, which had blown the market away the previous year. Myerson wanted to know whether any of Microsoft’s code could be saved. No one would leave the room until that question was answered, he said.

Seven hours later, the group had reached a tentative consensus: toss it all out and start over.

Toss it all and start over

The decision to design a new mobile operating system from scratch was a difficult one, and it gave Google an edge in introducing Android. But it turned out to be a huge feather in Myerson’s cap. The new Windows Phone was well-designed — if a bit light on functionality at first — and earned critical praise even as sales were faint.

Less than two years after the cage match, Myerson was promoted to head the entire Windows Phone group. Myerson "played a key and highly successful role ... by leading the engineering work on Windows Phone 7 and 7.5," CEO Steve Ballmer wrote in an internal memo announcing the change. "We have tremendous potential with Windows Phone."

Myerson’s ascent continued this week when Microsoft announced that the 40-year-old has been promoted to lead the most lucrative and crucial of the company’s four new technology divisions: the "operating systems engineering group." Basically that means Windows, the operating system that made Microsoft most of its money and now appears not just on PCs, but also in various derivatives on phones, tablets, PCs, and the Xbox. In other words, the backbone of everything Microsoft does.

The choice of Myerson over rising star Julie Larson-Green, who was head of engineering for Windows and now will head up the hardware group, may raise some eyebrows. Larson-Green is known for her poise and diplomacy, while Myerson crumples under the spotlight and is ungenerous with the press. On a conference call yesterday, The Verge asked a question about how the two will work together. Larson-Green jumped in with a sunny corporate answer immediately. Myerson hung back until he was called out by name, then gave a meandering response about innovation coming from Microsoft’s partners.

The choice of Myerson over rising star Julie Larson-Green may raise some eyebrows

Myerson can also be a bit ungracious. He’s called Android "a mess," and wondered on stage if Apple is "running out of steam, is iOS getting boring?" He trashed the competition again in an interview with Wired, in which he said Android is "confusing" and "chaos" and Apple is authoritarian.

Then there is the troubling fact that Windows Phone is good, but it’s not popular. Sales lag far behind iPhone and Android. The app selection is comparatively meager; Windows Phone has around 160,000 apps while its competitors have more than 800,000 each. The Windows Phone platform has also been criticized for being slow to roll out updates. After two years of Myerson rule, Windows Phone has yet to fully reach the "tremendous potential" Ballmer was so hopeful about.

Myerson never planned to work at Microsoft. He spent one semester at Trinity, the college of arts and sciences at Duke University, before transferring to a mechanical engineering major. In college, he waited tables and worked part time doing graphical simulations for the Environmental Protection Agency. After graduating, he took a job in the computer graphics industry until he became seduced by the lure of the internet and quit to start his own company, Interse Corporation.

The 24-year-old Myerson personally earned $16.5 million worth of stock

Interse built websites, and later, data mining software. It only took two years before it caught Bill Gates’ eye, and a sale closed soon after. The company was acquired by Microsoft in 1997 for an undisclosed price, although public records show that the 24-year-old Myerson personally received about $16.5 million worth of stock.

Myerson took a supporting job in "internet services business unit within the server applications division" and worked on Site Server, Windows Management Instrumentation, and BizTalk, among other products. He joined the group for Microsoft Exchange, the corporate email, contacts, and calendar software, in 2001 and led that team for eight years.

In 2009, mobile chief Andy Lees tapped Myerson to help revitalize the mobile group in the face of the iPhone threat. One of his first major hires was Windows Phone manager Joe Belfiore, who was largely responsible for the design of the new operating system.

Myerson had one other major victory as mobile chief, which likely paved the way for his promotion. Microsoft managed to build a good, some might say great, mobile operating system, but it didn’t have any killer phones. Furthermore, carriers were promoting Apple and Samsung phones to their customers, leaving Microsoft’s offerings to wither on the shelf.

Jo Harlow, Nokia’s executive vice president of smart devices, also went to Duke, and she and Myerson became close. He was instrumental in building Microsoft’s partnership with the Scandanavian handset maker. Since then, Nokia has become Microsoft’s closest ally in mobile. Teams from the two companies even went snowshoeing together in Finland.

Myerson was instrumental in building Microsoft's partnership with Nokia

Myerson is a company man; his younger brother even works at Microsoft. But his awkward public persona and partial failure on Windows Phone could hold him back. Promoting synergy between all the products that run Windows is a top priority for Microsoft now, based on the company’s rhetoric this week. But actually uniting the disparate products has proved a substantial challenge so far, to the point that some developers are wondering if it’s just talk.

It’s widely believed that Lees, Myerson’s benefactor and predecessor in the mobile group, was thrown under the bus. With all the challenges facing Microsoft, and the coming adjustment period after such a drastic reorganization, Myerson will have to sprint hard to avoid that fate.