On Nov 7, he sold 100,000 shares at an average of $41.7513. The following day, he sold another 200,000 shares at $42.2023 apiece.
The transactions on these two days has let Gupta pocket a total of more than $12.6 million.
Gupta, who will hand over the helm to deputy CEO Tan Su Shan next April, is for now left with just over 1.99 million shares, equivalent to 0.077% of the bank.
Just on Nov 7, DBS reported a new record of profitability, thanks to broad-based growth.
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The bank, in a bid to better return capital to shareholders, will embark on a $3 billion share buyback programme.
DBS shares ended Nov 11 at $42.75, slightly off the intra-day high of $42.98 but up 0.83% for the day.