@SamWCisneros I ran in to the very same problem. Many have. Your first mistake is believing that by completing all of the highest point assignments + using golden tickets and doing all the highest point assignments means that you SHOULD win. What about the being a Mayor part? When your Sim citizens are asking for entertainment are you giving it to them or ignoring them? When they ask for a house of worship, or for you to expand to the mountainside are you doing it, or ignoring them? Are they, (Your citizens), asking for maglev roads for the entire city, and are you working on it? Are you in control of your city's income, ( simoleons are a city's life's blood)...Are you to the point where when you start a contest with "x" amount of simoleons you can maintain that amount the entire game and maybe even finish the game with more simplelons than you started with? Where are you at with your City Achievements? (THIS IS A BIG DEAL...Found when you click on the Mayor's Mansion). If you're Journal is not complete, are you working on it? The reason you are not winning is because the Mayors you are competing with have completed more "Mayoral" tasks than you have and therefore are offered higher point assignments. A good start for you, (it sounds like to me), would be for you to complete some, or MORE, City Achievements, or you can just keep doing what your doing and keep driving yourself mad...Please at least consider trying this, and thanks for taking the time to read "my opinion" that works 😉