Kevan Thakrar, who was found guilty over six years ago of killing three drug dealers, was awarded more than 800 pounds by the same judge in April 2014 after items including his nose hair clippers were damaged in jail.
Last week's ruling at Milton Keynes County Court is the result of a claim made by the 27-year-oldin 2013, when he was a prisoner at HMP Woodhill in south east England.
Indeed, some would say that the fact that a claim of this kind can be dealt with at modest cost through the County Court system is a good advertisement for the civil justice system of this country.
"I am satisfied that the damage to the CDs must have been caused by the deliberate act of one or more prison officers."
Thakrar had complained that in the course of being moved prisons his stereo was broken, a number of CDs were damaged beyond repair and four of his books were lost, The Independent reported.
"We robustly defend claims made against the Prison Service where evidence allows, and have managed to successfully defend two thirds of prisoner claims over the last three years."
Thakrar was jailed in 2008 after he and his brother Miran used a sub-machine gun to kill Keith Cowell, 52, his son Matthew, 17, and Tony Dulieu, 33, the previous year.
The brothers were also sentenced for two attempted murders.
In March 2010, Thakrar severely injured three guards at HM Prison Frankland in County Durham after stabbing them with a broken bottle, but was cleared of two counts of attempted murder and three of wounding with intent after claiming he was suffering from post-traumatic stress disorder.
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