Liebskind was born in Nir Galim and studied at the Yeshivat Or Etzion. He was drafted into the Intelligence Corps of the Israel Defense Forces and upon discharge, worked as a private investigator. In 1997, he was one of the founding journalists at Makor Rishon and worked as an investigative reporter. In 2000, he began working at Maariv. Liebskind is married with five children.
Liebskind had several high-profile exposures:
- In 1999, he exposed Ehud Barak's non-profit organizations who funded Barak's elections' campaign, in violation of the political parties funding law.
- In 2008, he exposed that general Yoav Galant has taken over public lands in Moshav Amikam. This exposure led evantually to cancel Galant's appointment as Chief of General Staff of the IDF.
Liebskind won several awards and honors:
- Media Criticism Award (2002) - פרס ביקורת התקשורת
- Ometz Award (2007) - אות אומ"ץ
- Knight of Quality Government Award (2009) - אות אביר איכות השלטון
In recent years, Liebskind publishes a weekly column in Maariv's "Mosafshabat" which deals with the weekly political and actual affairs. Liebskind devotes most of his columns to criticize the Israeli media, which he claims have a left-wing bias. 
- E.g. Liebskind, Kalman (7.8.2010). "צה"ל, הנאצים ו"הארץ"" (in Hebrew). NRG Maariv. Retrieved 20 December 2011.
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