'Intelligent' fraudster Antony Malam enjoyed a lavish lifestyle – after conning the state out of £85,311.
Judge David Fletcher described the 60-year-old's level of offending as 'breathtaking'.
Stoke-on-Trent Crown Court heard the defendant wrongly claimed income support, employment support allowance, disability living allowance, housing benefit, council tax benefit, pension credits and incapacity benefit.
The claims – which were always fraudulent – ran from 2008 to 2014.
In a catalogue of deception, Malam:
Failed to declare his capital assets
Continued to claim UK benefits when living in the Philippines
Claimed housing benefits as a single person with no capital or savings – despite having more than £310,000 in November 2013 in the Philippines
Adopted a new name – Alan Johnson – in 2009 to claim even more benefits
Prosecutor Sarah Badrawy said: "It became clear the defendant was acting as a tenant and landlord using false documents to verify that position. On at least two occasions this defendant had conversations with the authorities indicating one of the tenants had gone to visit a friend and was in hospital when he was clearly aware he had died."
The court heard Malam was a frequent traveller abroad.
The prosecutor added: "It was established he had numerous bank accounts in the UK and abroad. He was substantially over the limit he would have been entitled to had his claims been legitimate."
The court heard Malam has paid back almost £100,000.
Richard Gibbs, mitigating, said: "He acknowledges the wrong he has committed. He apologises for what he has done. He has made clear financial recompense."
Malam, of Moorland Road, Burslem, admitted nine offences of benefit fraud and was jailed for 32 months.
Judge Fletcher told Malam: "The extent of your dishonesty is frankly breathtaking. Day-after-day in this court there is a procession of people who depend for their livelihood on benefits. Most of them are living on or close to the bread-line. At times you had £310,000 in an account in the Philippines when making these sort of claims, going to the extraordinary length of changing your name. The claims were fraudulent from the outset, with the proceeds helping to fund your lavish lifestyle. They were carried out over a lengthy period of time. This is one of the most serious offences of its type I have ever seen."
The investigation was carried out by the DWP, Staffordshire Police and Stoke-on-Trent City Council. It included a raid on his Burslem home.
DWP officer Claire Taylor said: "This exceptional investigation uncovered lengthy fraudulent claims for benefits."