Look at his first games with all those similar items bought... maybe he's a guy who employs a bot to farm items, but unlike other botters, he dedicated his whole life to scripting a decent Lich AI, slowly perfecting it so it would adapt to enemies malking item choices and having over 50% victories, dedicating his life with a passion not to playing the game, but to programming a bot that can play the game just as well as a human. His first step was Lich, but somewhere he has other four accounts and he is programming a team of bots capable of interacting with each other and proving the automated mind of a machine superior to the organic brains of mere human players. Slowly but steadily, his programming skills increase, until one day he will challenge the world's best teams at The International 6, where his team of bots will easily defeat puny humans and their imperfect strategies, boosting his popularity and making hundreds, thousands of people ask him to code a script for their account as well. And in the far future of 2020, the whole Dota 2 network will be entirely populated of bots, too lifelike to be identified by Steam administrators and too powerful for human players to even attempt matchmaking. But a resistence of humans by then will have risen, determined to take back what once belonged to human players. Chosen by Icefrog, a team of heroes will start climbing the MMR ladder again to reach unimaginable tops that the minds of the bots will never be able to replicate, so that the whole world will learn that yes, a human will always prevail over a machine, and the guy who programmed Lich and the others, now old, and exhausted, will present himself to Icefrog and fall on his knees, uttering "you win, my machines have failed", and he will cry before Icefrog, but with with a benevolent smile, he will be given a second chance, working at Valve, and thus we will get a new Holdout mode. And then in the end it turns out that he was Pendragon seeking revenge all along, and that he is Icefrog's long lost brother.
Or it could be just a loser who always picks Lich. One of the two, really.