The 77-year-old has spent most of his adult life in politics and the August 9 poll was believed to be his best chance, yet he narrowly lost to William Ruto, who had been his nemesis.
Questions abound as to whether Raila could rebrand himself as the firebrand opposition leader who could snap his fingers and send thousands pouring into the streets to protest against government action.
For a brief period, he seemed to have torn up his dissenting, rabble-rouser credentials as called a truce with the establishment, President Uhuru Kenya, for the sake of peace. Then Kenya was bereft of a genuine opposition and sounding board as he dallied with 'the devil' and ministers flocked to seek his blessing.
But Raila, once commanding legions of fanatical followers and credited with fighting for multiparty democracy and a much-admired Constitution, is in the painful position of taking his last stand, if he can.
Does fortune favour the bold or do good things come to those who are patient?
After his election loss, Raila has been faced with a storm in his Nyanza backyard as leaders blame each other over their loss. Many bungled nominations and the direct awarding of tickets to favourites outraged his supporters.
He is also is also staring at an implosion in ODM as party legislators heatedly dispute House leadership positions. Many counted on a Raila victory for his own advancement.
Will the master of reinvention take up the position of official opposition leader?
So, has Raila used up all the luck, goodwill and canniness that took him ever so close to his goal? If so, what next for a man who has been described as Kenya’s eternal presidential candidate, the master of reinvention and the riddle man?
President Ruto, Raila's long-time adversary, has surprisingly hinted that the ODM boss stands a chance of landing an appointment in his government, if he retires from politics. Ruto has ruled out a handshake with Raila and is that 'lifeline' significant or a figleaf?
It could really be toxic, leaving Kenya without resistance as Ruto bulldozes his way through the political landscape.
“When Raila Odinga decides to retire, I think there are roles he can play as a Kenyan leader. He can support the country in other initiatives, in other areas, maybe in the Great Lakes region because he has contacts there.
"He can work with the rest of us as an elder statesman, as a person who has served as Prime Minister of Kenya,” the President told the BBC on Monday.
He already is the AU High Representative for infrastructure.
Political commentator Joseph Mutua said Raila has chosen a low profile since he lost his Supreme Court position. “This could be a strategic move," Mutua said.
First, the majority of Kenyans believe the new President is on the right course and hence would not entertain anyone speaking ill of him. At some point, Kenyans will get tired of him [Ruto] and this will provide Raila an opportunity to hit back at Ruto and resuscitate his dwindling his political career,” he said.
Mutua said the recent demonstration by six ODM MPs against the IEBC must have been sanctioned by Raila.
“These MPs were known to be diehard supporters of Raila and so you would not expect them to participate in this without his blessings. To me, this could mean Raila believes he is still energetic and active, hence, not ready to hang up his boots,” he added.
One cannot rule out Raila opting to retire from politics for good.
“There is a talk that his close family members and his doctors have been pressuring him to retire from politics. They are said to be citing two grounds: his advanced age and health challenges,” Mutua added.
Raila entered Parliament in1992 and ran unsuccessfully for the presidency in 1997, 2007, 2013, 2017 and 2022, claiming to have been cheated of victory in the last four elections.
A section of his allies believe Raila still has a chance of clinching the highest office in the land before retiring
Former Cabinet Minister Kipruto Kirwa, who ditched Ruto for Raila in the run-up to the elections, said the Azimio leader could still be a formidable force in 2027.
The former UDA vice chair said all is not lost for Raila, despite his age.
“Raila may be 81 in the next election but he may still be formidable. To be elected, you do not need to be so energetic,” Kirwa said
Political commentator Fred Sasia said, however, Raila is at a crossroads since he lost an election many believed he was going to win.
“And age is also not doing him any favour. His political influence is dwindling countrywide. The traditional support he's always received from his Nyanza backyard is diminishing by the day,” he added.
Sasia added that a political powerhouse like Raila does not need to hang up his boots, he only needs to change politics.
“In 2013, many believed it was the end of the road for him, but he changed tact and came back stronger, even his ardent supporters couldn't fathom it," Sasia said.
"The distinctive factor now is that age has caught up with him, his passionate followers are not so passionate, change is not so close and his charisma is on trial," he said.
He said the decision to retire might not require his engagement since natural forces "will be deciding for him".
Raila has been accused of stifling democracy in ODM by deciding who holds what position and who gets elected or nominated, as in Nyanza.
Pending House leadership jobs and sharing of committee slots have brought the matter to fore; wrangling threatens to tear apart the 17-year-old party.
The storm in ODM is between the old guard and legislators who are serving, at most, their second term.
Embakasi East MP Babu Owino and Narok Senator Ledama Olekina, are leading the young lawmakers in the confrontation with the veterans led by ODM chairman John Mbadi.
Owino has argued Mbadi has already been awarded the nomination slot, and is also the party chair, giving him another House position would be unfair, he said.
Sasia said the life cycle of ODM could be coming to an end.
“New leaders must emerge, especially now that a new heir to Raila must front himself, and that can't happen under the same house. As they say, there can never exist two kings within a monarch at the same time,” he explained.
He said Raila may not groom a successor now and upcoming political leaders should take up the challenge.
“They should risk unpopularity, patiently explain their case to Raila's traditional supporters and confront prejudice, bigotry and vested interests. In doing that, the electorate will develop trust and slowly shift their political trust from the enigma to the new-found leader. Waiting to be endorsed is a lazy way of wanting power,” he explained.
He urged Raila not to back off from opposition politics.
“Resigning from his role would sound like betrayal to the people of Kenya. The only thing I foresee from the political enigma, is that he may be required to front a person like Wiper leader Kalonzo Musyoka as the face of opposition,” he added.
Mutua said he does not see Raila accepting any job offer that comes with conditions, such as Ruto's.
“I would not expect Raila to accept any job offered by Ruto if it will gag him from furthering opposition cause, as did the Handshake. He could read this as a setup,” he said.
Mutua added that the Azimio leader knows he will lose the support and confidence of his supporters by accepting a job offer from Ruto.
“The only job I know he can accept is that of regional or continental job because it will not tie his hands in pushing his political agenda here in Kenya.
Former President Uhuru Kenya knew this when he secured him a job as Africa Special Representative for Infrastructural development. Raila continued to represent the interests of his party.”
(Edited by V. Graham)
