Chee won't. Singapore has been in the longest bull run in history, from the early 1960s till today, with minor speed bumps like some recessions here and there. But the trend is still a continued bull run. As long as that is maintained, Chee will remain a loser.
The conservatives and labour parties take turns to win elections because neither party can sustain the country's success long enough to cement their grip on power. They do well for a few years, then mess things up big time and the opposition party wins, and the cycle repeats itself.
Singapore is different. It is a story of success for nearly 60 consecutive years under a single party that has improved Singapore from year to year. Chee will have no chance as majority of the voters don't want to rock the boat.