Monopoly Tryndamere

Start with a small bag of money. Get more money, bag gets bigger. Fill bag to beat opponents to death faster with a bigger bag of money. Monocle and top hat is a must. Mustache is a must. Expensive suit is a must. Money flying in all directions is a must.

Making this skin is also a must.

Edit: I can't draw well, if someone would take the time to draw something and leave it here that would be pretty cool.

Second Edit: I have actually put a bit of thought into this and believe that this skin suits Tryndamere very well. Less his character and lore (although a corporate barbarian could be a pretty interesting idea but im not knowledgeable enough about businesses to make this work properly) and more about how he behaves in a match. Your aim playing Tryndamere is to hoard as much gold as you can while taking enemy buildings until you are eventually 3 shotting whoever you can get close to represented both literally and figuratively by the growing bag of money with which you are beating them with.