Most of my knowledge of him comes from Texas history, so someone can touch up on a few things. I'm going to source what I don't know for sure.

Santa Anna's rise to fame began when he fought against the Spanish, whom were trying to re-conquer Mexico. He was very crafty in how he manipulated the political offices in order to gain fame and glory. Source 1 Source 2

Santa Anna was definitely loved during his prime years before the Texas Revolution, he was elected president 11 times even after the failures of the revolution. He definitely was a pretty cocky general, and it cost him during the Texas Revolution and Mexican-American War.

Let's start at the Texas Revolution and the famous Battle of the Alamo. The reasons Santa Anna decided to attack the Alamo was because he wanted the personal satisfaction of killing every single Texan as well as send a message to the Texan army that he would show no mercy. It would have been an even easier victory if he had waited for his cannons to arrive to the battle but instead attacked the Alamo with his troops which cost them heavy casualties.

Two events were to have said to cripple solider morale at this time, first off he executed Davy Crockett and a few other Texan soldiers that were captured. Secondly, he agreed to retreat from Texas and recognize their independence after the defeat at San Jacinto. A man named Jose Enrique de la Pena was a solider during the revolution and kept a diary depicting these events. He explicitly expressed his and other soldier's disappointment in these decisions.

Now between the revolution and the Mexican-American War, Santa Anna fought in the Pastry Wars against the French in which he used his fame to run for President once again. He enacted a few taxing policies that made him unpopular with many Mexican officials and was jailed (Mexican's were outspoken against big central governments). He was released so he could command the Mexican army against the American's. Fortunately for the Americans, Santa Anna was a pretty bad general which led to the defeat the Mexican army and thus the treaty of Guadalupe-Hildago.

Santa Anna was exiled to Jamaica after the war, I don't know much about him after that but apparently he kept trying to run for re-election but was ignored by the Mexican government.