Philipps has received attention since at least the early 2000s, in relation to his business and legal affairs. He was first declared bankrupt in 2002, and subsequently held directorships in several companies. In September 2008, having been denied bail as a flight risk, Philipps spent more than a year in prison in Nuremberg. Claims were investigated that he used more than £350,000 of company funds on promoting an opera singer, £12,000 to rent a private jet and £5,000 on a shotgun from James Purdey. He was eventually given a two-year suspended prison sentence by a German court for mismanagement of funds related to his construction company Hans Brochier, from which he transferred a seven-figure sum to a newly registered company in the UK in 2005. In 2009 he appealed against the sentence. In September 2010, Philipps' West Sussex property, Strange Place, in Northchapel, was repossessed by Barclays Bank. In March 2011, he was declared bankrupt for a second time, and in November 2011 his wife, Viscountess St Davids, was sued for unpaid debts. In March 2012, Philipps unsuccessfully sued offshore legal advisors Corporate & Chancery Group for £110 million in the Supreme Court of Mauritius, alleging fraud and mismanagement. In February 2016, he was declared bankrupt for a third time.
Menacing communications
Following a complaint made in November 2016, Philipps was arrested in January 2017 by Metropolitan Police officers investigating online abuse against a 51-year-old woman. In March 2017, he was charged with malicious communications with racially aggravated factors, over alleged threats against Gina Miller, who was behind a successful legal challenge against the UK government's intention to give notice to leave the European Union without an act of parliament. Among other communications, he posted on Facebook: "£5,000 for the first person to 'accidentally' run over this bloody troublesome first generation immigrant" and "If this is what we should expect from immigrants, send them back to their stinking jungles". He pleaded 'not guilty' to three charges of menacing communication under section 127 of the Communications Act 2003 when he appeared at Westminster Magistrates' Court on 2 May 2017. At the May hearing, the prosecution said the crown would seek an extended sentence because of the racial aggravation factor. He was found guilty of two charges at his trial on 11 July 2017, at which he defended himself. Philipps was also convicted for comments made in response to a news article about an immigrant, in which he had written: "I will open the bidding. £2,000 in cash for the first person to carve Arnold Sube into pieces. Piece of shit". Philipps, who described his own comments as "satire", was sentenced to 12 weeks in prison. He was released on bail, pending an appeal. The appeal was abandoned by Philipps on 25 August 2017 some fifteen minutes after Judge Deborah Taylor informed Southwark Crown Court that there was a risk his sentence could be increased. Philipps will now serve the remainder of his original sentence.