Lennie Smith
Leonard /Lennie Smith, a violent male who identified as a trans woman subsequent to his convictions, was jailed for 10 years in 1992 for a series of sex attacks on a six-year-old boy. In 1987, Smith, aged 31, had been one of 12 men convicted of sexual offences against two boys aged 13, one of 11 and one aged 14. In the early 80s he served a year in prison after being convicted of burglary, theft and criminal damage. He also had at least five convictions for gross indecency dating back to when he was a rent boy and drag queen in the late 70s before he turned pimp.
Smith was also charged with the murder of seven year old Mark Tildesley in 1987 but charges were subsequently dropped as the person who named him as the killer (Leslie Bailey) was himself convicted of the manslaughter of the child (having confessed to having been present) and this was insufficient evidence to secure a conviction without a confession from Smith.
While in voluntary custody at a special unit in HMP Nottingham in 1996, Smith, now aged 42, reportedly sought gender reassignment to live as a trans woman, claiming many of his offences were the result of his ‘confused’ sexuality. However, criminologists believed this was a ploy to convince police and public that he was a reformed character.

Daily Mirror 23 Oct 1992 via Spotlight
Smith was the ringleader of a group of paedophile men including Sidney Cooke, Robert Oliver (who changed his name to Karl Curtis) and Leslie Bailey who are believed to have tortured, raped and killed at least 5 young boys in the 1980s. Oliver was jailed for 15 years in for the manslaughter of 14-year old Jason Swift; Smith was also arrested for the killing but never charged.
Smith died of AIDS aged 51 in 2006.
Further details of Smith’s catalogue of crimes of sexual violence against children are available in these blog posts:
The Needle https://theneedleblog.wordpress.com/2015/01/03/operations-stranger-and-orchid-lennie-smith/ archive
Prison Documents relating to Lennie Smith https://theneedleblog.wordpress.com/2017/06/06/prison-documents-relating-to-lennie-smith/ archive
Operation Greenlight https://webbrain.com/brainpage/brain/0FE31538-2121-8495-33A5-86073BE95DE1/thought/3997#-3687 archive
A 1999 Channel 4 Dispatches documentary on Lennie Smith entitled ‘Britain’s Most Dangerous Man’ is available on YouTube here
In 2018 it emerged that Smith had links to another paedophile ring in Southend, Essex and local media used the Freedom of Information Act to unlock his police records – see Daily Gazette article here [archive]
Lennie Smith photo via The Needle
Media reports
Archived copies of newspaper coverage https://spotlightonabuse.wordpress.com/tag/lennie-smith/ archive
Ham & High https://www.hamhigh.co.uk/news/24972833.north-london-paedophile-lennie-smiths-police-files-released/ archive
BBC Protest at paedophile release http://news.bbc.co.uk/2/hi/uk_news/369688.stm archive
North Wales News https://www.dailypost.co.uk/news/north-wales-news/families-hostel-fury-2915513 archive
Daily Mail (archived) https://www.highbeam.com/doc/1G1-109707196.html
Sunday Mirror (archived) http://www.thefreelibrary.com/NEXT+STOP+HELL;+EXCLUSIVE+Worst+paedophile+in+Britain+dies+of+AIDS+in…-a0147708938 archive archive
Hackney Gazette (archived) https://spotlightonabuse.wordpress.com/2013/07/09/men-procured-and-corrupted-boys-court-told-12-6-87/ archive
The Guardian https://www.theguardian.com/uk/1999/jul/20/nickhopkins archive
Birmingham Mail 2006 https://www.thefreelibrary.com/VICTIMS+OF+AIDS+PAEDOPHILE+MAY+NEVER+BE+FOUND.-a0147967203 archive
Birmingham Mail 1999 (archived) https://www.thefreelibrary.com/Child+sex+perverts+in+bail+hostel+alert.-a074416440 archive
The Mirror 2000 https://www.thefreelibrary.com/Shame+of+the+Dirty+Dozen+is+living+on%3B+While+rest+of+the+world+talks…-a063899412 archive
The Mirror 1997 (archived) https://www.thefreelibrary.com/Gang+that+preyed+on+innocent+kids.-a061070017 archive
The Independent http://www.independent.co.uk/news/uk/paedophile-gets-life-for-killing-boy-7-at-orgy-homosexual-ring-abducted-children-and-drugged-them-1559081.html archive
Daily Mail (archived) https://www.highbeam.com/doc/1G1-109768445.html