When the Securities and Exchange Act (“SEA”) was amended in 2004, the penalty of substantial financial crimes, including insider trading, regulated in Para. II of Article 171 was raised from 3-10 years in prison to not less than 7 years where the gain of the offense is NT 100M or more. However, neither the SEA nor its ratio legis provided a specific criterion to calculate the Proceeds of Crime, the gain, from insider trading. While the SEA was amended in 2018, the language“Proceeds of Crime”in Para. II of Article 171 was revised into“the value of property or property interests gained by the commission of an offense”. Nevertheless, the issue of how to calculate the value of property or property interests gained by the commission of an offense remained unclear.To unify the split opinions among courts regarding the abovementioned controversy, the Grand Court of the Supreme Court laid down the criteria in its Ruling 108 Tai-shan-da Tze No. 4349 on May 19th, 2021. In terms of realized gain, the Grand Court adopted the“Actual Gain Approach”, while with regard to unrealized gain, the Court took the“Presumptive Gain Method”to measure the amount of gain from insider trading. The Ruling has, without a doubt, resolved the split-court controversy in one way, yet, left some unresolved issues in another.This article reviews the split opinions regarding calculation of gains from insider trading among Taiwanese courts and compares with those in the U.S. courts and practices. Finally, the Author analyzes the pros and cons of different approaches adopted by the courts at issue and try to provide suggestions in response to the Grand Court’s Ruling and for further law amendment.