In 1980, Kuttab began his career at Al-Fajr, an English-language weekly newspaper. Over the next seven years, he was promoted to features editor and then managing editor. In 1987, he left Al-Fajr for Al-Quds, an Arabic-language daily newspaper based in East Jerusalem. He also contributed to the Jerusalem Post. During this period, he became the first Palestinian to receive an exclusive interview with Yitzhak Rabin, as well as from Shimon Peres and several other Israeli leaders.

Kuttab was critical of press censorship by both the Israel government and the Palestinian Authority. On several occasions, he participated in rallies against Israeli censorship, resulting in his being arrested and searched. In 1994, Kuttab led journalists to rally in protest of the banning of the daily newspaper Al-Nahar by the Palestinian National Authority. Al-Quds subsequently fired Kuttab at the direct order of President Yasir Arafat. Kuttab continued to work as a journalist, however, writing for papers including the Daily Telegraph, Daily Yomuri, International Herald Tribune, Los Angeles Times, The New York Times, and The Washington Post. In April 1996, he also created the Arabic Media Internet Network, an online magazine for uncensored Palestinian journalism.

In May 1997, Kuttab was detained without charge by Arafat’s government, reportedly for producing live broadcasts of Palestinian Legislative Council meetings. He was released one week later following local and international pressure.

In 2000, the Austria-based International Press Institute named him one of its fifty World Press Freedom Heroes of the previous fifty years.