The insurer claims that Peter Tan Shou Yi caused 244 of its agents to resign and join competitor Aviva in 2016, after he offered them loyalty bonuses.
The company also claims that he was supposed to receive an annual bonus from Aviva if he managed to get 100 more agents on board.
At a High Court hearing in Singapore, Prudential estimated losses amounted to around S$2.5bn (£1.5bn, $1.8bn, €1.6bn).
It said that it lost S$300m in profits if the agents stayed until 2025, and S$2.5bn if they stayed in perpetuity, reported local newspaper The Straits Times.
The exodus left some 70,000 policies without agents.
“The defendants would like the court to believe that this mass migration… was the result of coincidence, normal attrition, and possibly even loyalty to [Tan]”, Prudential’s lawyers said according to the Singapore newspaper.
“One swallow may not make a summer, but 244 agents make it an unlawful, illegitimate en bloc solicitation of Prudential’s agents.”
They also allege that Tan forced the agents to sign non-disclosure agreements and warned them not to inform Prudential about the mass resignation.
The lawyers argued that Tan’s actions breached his contract, which had a non-solicitation clause, set out in 2010.
However, Tan’s representatives argued that this did not apply to their client as the clause was only introduced for and signed by financial advisers or financial consultants in agreement with Prudential, and he was neither of those.
In return, Tan is counter-suing for wrongful termination of his contract and is claiming loss and damages as well.