There's a very good interview on NPR with John B. Judis who wrote
The Folly of Empire: What George W. Bush Could Learn from Theodore Roosevelt and Woodrow Wilson. He compares the folly of McKinley's annexation of the Philippines after the Spanish-American war and the fierce nationalist resistance that it engendered with Iraqi Freedom and Bush's occupation and oxymoronic imposed democracy on Iraq.
Roosevelt initially supported McKinley's imperialism, but came to see the annexation as a mistake. He referred to the Philippines as "our heel of Achilles."
"After Woodrow Wilson became president, he and the Democrats backed Philippine independence, but were thwarted by Republicans who still nurtured dreams of American empire. Only in 1946, after reconquering the Philippines from Japan, did the United States finally grant independence -- and even then it retained military bases and special privileges for American corporations." (Judis)
'Folly of Empire' Offers Critique of U.S. Imperialism
An exerpt from the book is included on the webpage.