LAST month, on the same day The New York Times praised Google for standing up to censorship in China, a sister newspaper, The International Herald Tribune, apologized to Singapore’s rulers and agreed to pay damages because it broke a 1994 legal agreement and referred to them in a way they did not like.

The rulers had sued for defamation 16 years ago, saying a Herald Tribune Op-Ed column had implied that they got their jobs through nepotism. The paper wound up paying $678,000 and promising not to do it again. But in February, it named Lee Kuan Yew, the founding prime minister, and his son, Lee Hsien Loong, the prime minister now, in an Op-Ed article about Asian political dynasties.

After the Lees objected, the paper said its language “may have been understood by readers to infer that the younger Mr. Lee did not achieve his position through merit. We wish to state clearly that this inference was not intended.” The Herald Tribune, wholly owned by The New York Times Company, apologized for “any distress or embarrassment” suffered by the Lees. The statement was published in the paper and on the Web site it shares with The Times.

Some readers were astonished that a news organization with a long history of standing up for First Amendment values would appear to bow obsequiously to an authoritarian regime that makes no secret of its determination to cow critics, including Western news organizations, through aggressive libel actions. Singapore’s leaders use a local court system in which, according to Stuart Karle, a former general counsel of The Wall Street Journal, they have never lost a libel suit.