Rajiv Rai specializes in tax controversy and dispute resolution. As a former in-house counsel with the Inland Revenue Authority of Singapore (IRAS), he led and assisted in numerous high-value and complex matters for the comptrollers and chief assessor before the various Tax Boards of Review and the High Court of Singapore. As a former deputy public prosecutor, Rajiv has experience in both criminal and regulatory matters.
Prior to joining Morgan Lewis, Rajiv spent close to four years as an in-house counsel with the IRAS, where he advised on various complex tax issues that would arise due to commercial arrangements enacted to avoid tax liabilities. These arrangements included cross-border routing of funds, assignment of introducer fees, setup of complex corporate structures, and bribery of foreign officials. Rajiv also led and assisted on various litigation matters conducted before the Tax Boards of Review and the High Court. For example, in Bollywood Veggies Pte Ltd. v. Chief Assessor  SGHC 233, he successfully convinced the High Court to affirm the chief assessor’s decision to include farms in the valuation list for property tax purposes.
Rajiv was also responsible for overhauling the IRAS’s sentencing framework in relation to income tax offences under the Income Tax Act. He successfully convinced the state courts to adopt the IRAS’s new sentencing approach in PP v. Lin Shaohua  SGMC 53. This new sentencing approach was subsequently endorsed by the High Court in Lin Shaohua v. PP  SGHC 138. He also advised the IRAS investigative division on instituting protocols for the exercise of its (then) newly granted arrest powers, compliance with the Criminal Procedure Code, and evidential chain of custody issues.
Rajiv also possesses a strong regulatory background as a former deputy public prosecutor with the Singapore Attorney-General’s Chambers. As a prosecutor, Rajiv served as a legal adviser to various enforcement agencies and prosecuted various serious crimes (including rape, drug trafficking, and financial and technology crimes) at various levels of the Singapore courts. Rajiv was involved in numerous high-profile criminal prosecutions such as PP v. James Raj s/o Arokiasamy  SGDC 36—the prosecution of “the Messiah,” an infamous hacker who had infiltrated and defaced websites belonging to various government agencies—and PP v. Gopal Mahey (published in The Straits Times on September 16, 2016), the prosecution of a prison drug counselor involved in the trafficking of drugs.
Dean’s List, Academic Year 2011–2012
Distinction in Mediation, Singapore Part B Bar Examinations
Advanced Certificate in Regulatory Compliance (Financial Crimes) (Merit), International Compliance Association
Income Tax I, Singapore Tax Academy
Goods and Services Tax I & II, Singapore Tax Academy
International Tax I, Singapore Tax Academy