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Politics permeated all aspects of Shimon's life, personal and professional. He was political as a painter, as a writer, as a journalist, as a poet and, even, as a writer of children' books. This is clearly evident in his drawings, prints and paintings from the 1950s of Jewish and Arab workers in the style of social realism (see Art), in his angry poems against the occupation (see Poetry), in his book, the White Flag Principle (see Books) and in his cartoons and columns for the Israeli press (see Journalism). The Six Days' War and the occupation led to his final politicisation. In this section the focus is on his life events, works of art and writings that were explicitly politically motivated and had political objectives.

He became a communist soon after the establishment of the State of Israel (read My introduction to Communism and Karl Marx). He was aware of the plight of the Arabs who lived in the Jewish state from the start, and refused to benefit from the privileges accessible to the conqueror (read about The tale of three houses).

The Six Days' War and the occupation changed his life completely. In direct contrast to the vast majority of Israelis who celebrated the victory, Shimon immediately understood the dangers behind the occupation not only for the Arabs but also for the Israelis. Just a few weeks after the end of the war he wrote a letter to the editor of Ha'aretz, in which he expressed, with faux naivety, his surprise about referring to the territories conquered in the war as ‘liberated land' instead of ‘occupied land' and asked sarcastically if there are yet more lands that needed to be liberated (read about the letter to the editor in The aftermath of the Six Days' War). On 22nd September 1968 Ha'aretz, the daily newspaper he worked for, published a paid advertisement [H] against the occupation written by Shimon (read the English translation of the advert, the story behind it and the Israeli public's response to it, in The aftermath of the Six Days' War). While at the time, the advert aroused verbal violence, calls for destroying his books and discontinuing his column in Ha'aretz, 30 years later it is remembered (by some) as a manifestation of prophetic insight. (read Michael B's column [H], about the advert just after the invasion of Iraq, and in Gideon Spiro's column [H].

Following the publication of the advert, Shimon's life became untenable in Israel, mainly, because he realised that there was no space there to fight against the occupation. He decided to leave the country and publish a satirical magazine, Israel Imperial News, in London, which would show the world Israel's real face. Read about the events around its publication in Israel Imperial News (1968) and beyond, see examples of newspaper articles (one and two) [H] appearing in the Israeli press about his and his friends' activities in London, and a photograph of one of many demonstrations staged by the handful of Israelis against the occupation at the time in London, in front of the Israeli Embassy.

In consequence of Shimon's activities against the occupation in London (the publication of the Israel Imperial News, letters to the Times, a television interview with Joan Bakewell, an article for the Daily Telegraph on the first anniversary of the Six Days' War), he was commissioned to write a book about the Israel-Arab conflict, which eventually resulted in his writing the White Flag Principle (see Books).

When he retired, after a long period of silence during which Shimon worked as a builder, he returned to writing, painting and politics. In 1990 he was commissioned by Hadashot, an Israeli evening paper that no longer exists, to write about the conflict and solution to the conflict. The article appeared on 9th March with the title Peace Now is Not Enough [H] in which he advocates a radical one-state solution.

In response to the second intifada, a new wave of political activities started in London. There were meetings and desperate discussions. Shimon designed a new Israeli flag that fitted better the reality of the situation than the traditional one with the star of David on. The flag was and still being carried by his friends in demonstrations in support of the Palestinians. With the support and help of his anti-Zionist friends he published a small volume of political poems with the title Shirey Herpat Hakibush (Israel's occupation of Palestine: Poems of disgrace) and distributed it widely both in Israel and Europe (see Poetry); in 2001 and 2002 he published two new print editions of Israel Imperial News (see magazine covers ) and started the Israel Imperial News website, which reproduced the 1968 and 2001 and 2002 editions of the magazine in full and continued to add further issues until 2007 with articles reproduced from the Israeli and world press, among them articles by Moshe Machover, Tanya Reinhart, Amira Hass, Gideon Levy, a poem by Hanoch Levin and some original contributions written specifically for Israel Imperial News .

In 2004, The Michelin Guide was published (read the guide in full at the Israel Imperial News website, read about the saga of the Michelin Guide in The tourist guide that never was ) and see Christopher Sykes' film Dear Mr Tzabar, on YouTube.