He wasn't a top leader of the IDF, but like virtually all Jewish Israeli's he did serve in their military. According to his biography on the web site "Zionism and Israel" (an apparently pro Israel site):
Olmert served in the IDF as combat infantry unit (Golani) officer. He was also a military correspondent for the IDF journal Bamahane.
It may be that his time as a journalist tainted his world view. Their news outlets are notoriously pacifist. They want to be loved by the Europeans too much.
Israeli PM is not a job for the timid...I believe the Israeli's made a serious mistake when they did not put Netanyahu back in office.
Elections have consequences...that message should be pounded into the heads of every American. After the Palestinians shot themselves in the foot by electing Hamas, and Louisiana's elected officials letting the state down, it shouldn't be difficult to get people to listen.
Medved was saying Olmert is a lawyer, and tries to solve disputes with words, rather than with force. Bring back Bibi.
Thanks for the full info on him I suspect you are right the journalist part of him personality is coming into play here.