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In 1836, Santa Anna and several thousand soldiers marched to Texas in order to quell the rebellion following Texas's proclamation of independence from Mexico. Two thousand of his soldiers faced off against 188 Texian rebels at the fortified Alamo mission, lead by Colonel's Davy Crockett and Jim Bowie, and Lieutenant Colonel William B. Travis. After a 13-day siege, Santa Anna attacked the mission on March 6th, where he was ultimately victorious in eliminating all of the Texian rebels in a heroic defeat which history would remember as the Battle of the Alamo. (DS9: "Wrongs Darker Than Death or Night")
In early-2375, Miles O'Brien and Julian Bashir created a holosuite program that recreated the Battle of the Alamo, with all of the key players, including Santa Anna. While handing out the roles of who played who, they gave the role of 'General Santa Anna' to Odo. (DS9: "Afterimage") Odo later told Bashir to give Santa Anna his regards. (DS9: "Prodigal Daughter")
After experiencing the battle, they later had a heated discussion on the subject in Quark's. O'Brien, believing that Santa Anna executed Crockett at the battle, supported his decision with the fact that Santa Anna didn't care about the "rules of war," and therefore would have considered the execution a point of pride. (DS9: "Once More Unto the Breach")
Bashir, fed up with constantly losing the battle, offered O'Brien a few suggestions on how to improve their chances. O'Brien, wishing to have no involvement with such blasphemy, told Bashir if he wanted to win then he should be Santa Anna – he wins every time. (DS9: "The Changing Face of Evil")