Monday's announcement of the presidential election winner by Independent Electoral and Boundaries Commission (IEBC) chairman Wafula Chebukati could however force the Ukambani kingpin to reconsider his options even as Raila seeks "redress" in court.
And known to be a man of many political Damascus moments, pundits argue that Kalonzo's options are not limited; he could close ranks with his political nemesis and President-elect Ruto, or stick it out with Raila in the murky corridors of justice with the hope that a verdict would eventually catapult his side to power and with it offer a launching pad for his presidential bid.
"The safest play for Kalonzo is to wait for Ruto to form government if his win is upheld by the court, be a fierce critic of his administration while in the opposition and offer solutions for the same and this way he will get the clout to give him the impetus to run for office in the next election," said Prof Edward Kisiangani, a political analyst.
"Kalonzo cannot plan around Ruto if he wants to ascend to presidency because Ruto will definitely seek another term come 2027," he added.
In his pre-election campaigns , Ruto - then an estranged Deputy President- had stated he would absorb the Wiper leader into his government should he clinch power.
In his tour of the Ukambani, the President-elect was appalled by Raila's decision to subject Kalonzo to running mate interview.
"Kalonzo has stood with him (Raila) since 2013 and it was a mockery for Raila to subject Kalonzo to any form of an interview. Imagine someone asking Kalonzo what's your name, your education level, and in the end, you conclude he has failed. This was ridicule to this community, and I assure you if I win, I will absorb him into my government," Ruto said.
"Now he (Raila) has promised to support Kalonzo in 2037 which is a lie. Years will have gone," he added.
Political analyst Tom Mboya avers that while the Wiper leader would reap big by joining forces with Ruto after he has been sworn in and possibly land the position of Chief minister, it would be premature of him to abandon the Azimio faction which is still contesting the poll outcome.
"Kalonzo must now consider what puts him in the best position to campaign for the 2027 Presidency; will it be by joining the government of the day (should the court uphold Ruto's win) or is it by remaining in opposition and going against the government of the day and being vocal about it?" posed Mboya.
Pundits argue that Kalonzo must graduate from under the Raila type of politics, forget the kingpin style of politics and forge his own political identity to ensure he amasses support from across the country.
Prof Kisiangani said should the Wiper leader join the Kenya Kwanza administration, he would be rendered politically irrelevant and he should be ready to shelve his presidential ambitions and support Ruto in exchange for a share and position in government.
However, Mboya disagreed: "Kalonzo will remain politically relevant should he join the government of the day or stay in the opposition. The positioning he has within Azimio and the votes he delivered in the just concluded elections show that he is not someone who can be ignored."
According to IEBC dats Kalonzo deliver to Raila approximately 1 million Ukambani votes in the just concluded polls.
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In Kitui, Machakos and Makueni counties, Raila managed 769,985 votes while Ruto got 250,188 votes. It is estimated that Kalonzo's support in Ukambani diaspora bases - Embakasi's in Nairobi, Mathare, Makadara, Starehe and Makadara - pushed this vote to one million.