The man leading the pack to take over as the fourth Prime Minister, Finance Minister Heng Swee Keat, had a massive stroke 15 months ago and has yet to recover fully.
Last week, a curious announcement that Minister of Social and Family Development Tan Chuan-Jin was being nominated for Speaker of Parliament, which many consider a demotion, became a talking point.
Tan replaces Halimah Yacob who this week rose by default to become Singapore's first female president
after other potential contenders fell foul of new rules.
Tan is a member of a core team of ruling People's Action Party (PAP) politicians being groomed to run Singapore as Prime Minister Lee Hsien Loong prepares to step aside after the next election, which must be held by January 15, 2021.
He served in the Singapore Armed Forces for almost 24 years before turning to politics in 2011, with roles in a number of ministries. He's also the President of the Singapore National Olympic Council, and an advisor to the National Council of Social Service.
Add to these events the scare that Lee gave to the nation when he nearly collapsed while delivering Singapore's version of the "State of Union" address one year ago
, it is clear that political succession is facing a huge setback.
The nomination of Tan, 49, as Speaker, a role he started on Monday, is the most intriguing and leaves many awkward questions which have yet to be answered fully.
For instance, why move a high-flying military general, who was hand-picked to join the ruling party to fight the general elections just six years ago, to a less powerful, less meaningful and less lucrative job as Speaker?
The online world is having a field day questioning the official explanations. PM Lee said Tan is the right politician to preside over Parliamentary debates to ensure full and fair discussions of national issues.
"Chuan-Jin has the temperament and personality for this role," Lee said in a surprise statement last week.
One news website asked pointedly, referring to a mini-reshuffle that had to be done because of Tan's departure from the Cabinet: Wouldn't all this not have been necessary if Tan, a young, energetic and passionate minister had not been moved?
Another asked: Is this a signal that Tan has not made the cut to be in the elite team to govern tomorrow's Singapore? It answered its own question. That does not seem to be the case as Tan rose up the Cabinet ladder to become a full minister just five years after he entered politics.
As Singaporeans debate the rather unusual appointment, the received wisdom is that the leadership's changing of the baton is causing concern as the previous changes have been so well-oiled and predictable.
Way before Lee Kuan Yew decided to step aside in 1990, the public knew that Goh Chok Tong would take over, and way before Goh even became PM in 2004, it was generally accepted that Lee's son, the current PM, would become PM No 3.
This kind of a smooth and predictable handover has been a Singapore hallmark which made the country a haven for investors and foreigners flocking to put in their money and sink roots here. Now, the next leader is not even in sight making this safe haven a little unpredictable, even a little vulnerable.
On many other fronts, Singapore is facing uncertain times. The economy is trudging along with no new ideas to push it forward, productivity is still lagging, an aging population and a lack of decisive measures to bring in foreign labor are frustrating employers, a muscular China and a clueless America are putting pressure on a leadership trying to read the tea leaves accurately. It is like a perfect storm coming together to wreak havoc on a country that has now to grapple with who will lead the country post-2021.
There is one bright spot, though. The leaders under Lee can still be relied upon to serve if the need arises. Lee will be 69 in 2021, Deputy Prime Ministers Teo Chee Hean, 66, and Tharman Shanmugaratnam, 64. The leadership can keep the gunpowder dry and draw on it if a rainy day approaches.