Wellington was certainly a popular winner. So were Patton, MacArthur, Montgomery, Eisenhower, General Zhukov (in Russia, anyway), George Washington, the Marquis De Lafayette, Richard the Lionhearted, Julius Caesar (popular with some, but not all), Alexander the Great, Napoleon (most of the time)...

Seems to me winners are almost always popular, but tragic deaths in battle make for great songs, as do the tragic sinkings of ships.