He has modelled himself as a protean, with an open mind to change tough political stands, and even work with those he has been at odds with. This happened in 2008 when he struck a deal with President Mwai Kibaki to end the post-election violence that followed the hotly contested 2007 presidential election. He would be appointed prime minister in the grand coalition government.
Raila displayed a similar attitude after the 2017 elections when talks between him and President Uhuru Kenyatta bore the infamous "handshake". Uhuru and Raila were at loggerheads after the opposition chief accused the president of snatching his victory, just as was the case with Kibaki. In the process, Raila ended up with a job at the AU, a position Uhuru and his government helped him to secure. Uhuru and Raila became friends, even campaigning together in the last elections.
After emerging as sworn enemies following the August 2022 polls, Raila and President William Ruto surprised friends and foes recently with their newfound friendship , with the government going all out to campaign for Raila's bid for the AU job.
To millions of his supporters, Raila is a fighter for political reforms and social justice.
While his critics view him as a disrupter, they also admit he does not hold onto grudges. Those who had been his greatest critics in President Ruto's regime have now transformed into his greatest supporters, campaigning for his AU job bid him across the continent.
Even those who have been pushing him to retire from politics have metamorphosed into his strongest supporters in the latest campaign.
Observers say it is hard to ignore Raila because of his bag of tricks and a massive support base that has always kept him relevant in Kenyan politics.
Raila, who has kept four successive governments on toes as opposition chief, has surprisingly managed to weave his way to the heart of power.
In the last few weeks, Raila has left even his closest allies puzzled over his next move as he trudges along a new path of continental politics.
Constitutional lawyer Joshua Nyamori describes Raila as a master of cartwheels, a statesman, an enigma of politics, and a prince . "You may start a journey with Agwambo but get surprised that it is Amollo in the driving seat mid-way," Nyamori says.
In Azimio, Raila's mysteriousness has kept his allies and coalition partners on the edge, confused about whether they should support the push for him to quit politics. The question of who his possible successor would be has been lingering with Raila saying nothing about it.
Political analyst Mark Bichachi says Raila is successful in life and politics because he has always stood for what he believes in.
Bichachi opines that Raila has been consistent in his whistle-blowing, defence of the people, and willingness to step off the ledge when things appear to be getting out of hand.
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"He is bold enough to take actions that most politicians would fear taking," Bichachi says, adding; "Raila has no permanent enemies and is always willing to make peace with his rivals."
"He is also a good networker maintaining his grassroots connections and being available to his long-standing allies," Bichachi says.
His journey dates back to the early 90s when Raila first plunged into politics. His first assignment, it appeared, was to fight for what his father, Jaramogo Oginga Odinga, had bequeathed a rival, Wamalwa Kijana. Against all odds and counsel from his fathers' allies, Raila fought for what he believed was his and managed to grab his father's political base in Western Kenya. His allies say Raila stands for what he believes and has invested heavily in intelligence and the element of surprise. They claim that not even some of his closest allies know his dealings.
Raila effortlessly rallies his followers to back his decisions. The decision to enter into a truce with President Ruto to the extent of earning the government's support for his AU Commission job bid appears to have warmed the hearts of his supporters.
Last week, Ruto and his allies received a warm welcome during their visit to Nyanza, Raila's political base.
"He is one daring man. He has won and kept a critical mass of sympathetic followers. It doesn't matter what everyone else thinks about him, they will rise or fall with him, regardless of where he goes, or what the hand of fate gives him," argues Barack Muluka, a communication consultant.
What is happening between Raila and Ruto now is a replica of the 2018 Handshake with Uhuru that suddenly turned the former president into a local hero in Raila's support bases.
Then, Raila kept the talks with Uhuru a secret that only his eldest brother Oburu Oginga, and Suna East MP Junet Mohamed were privy to.
In a past interview with a senior ODM official, they only became aware of Raila's move when they got an alert that the two leaders were to issue a joint press statement.
"It was a huge surprise but we always support our leader because he means well for the people and every decision he has made has strengthened reforms in Kenya," says the official who did not wish to be named.
Raila struck deals with successive governments and turned perceived political foes into strong allies.
After he lost in the 1997 presidential elections, Raila abandoned the fractured opposition and joined forces with President Daniel Moi, earning himself and a few of his allies slots in the Cabinet. This followed the merger of Kanu and his NDP.
Additionally, working with Moi saw him become Kanu's secretary general. The development warmed the hearts of Nyanza's Raila backyard to Moi. However, this irked the opposition and later split the ruling party.
Many are waiting to see who Raila, who has built the careers of many politicians, will endorse as his successor. Whoever will inherit his position faces the daunting task of uniting an opposition leadership fraught with suspicions and a mass of following left in a state of uncertainty.
In ODM, Raila has been facing a challenge with MPs the party has branded betrayers for working with Kenya Kwanza and stifling the agenda of the opposition. Here, Raila appears to have adopted two different strategies regarding his allies.
While he has been tolerant with ODM lawmakers from other regions at a time when his coalition did not recognize Ruto's administration, the situation was different in Nyanza. In Nyanza, all those who jumped ship and courted the government were expelled by the party and are still fighting, legally, to get back into the party.
Raila considers party hopping "political prostitution" and is among the issues he is hoping to put a stop to through the implementation of the National Dialogue Committee report.
On Friday, while speaking in Akala market in Siaya, Raila said ending defections is among the recommendations contained in the report. "We want all those who decamped to go for a by-election," he said.
ODM chairman John Mbadi says Raila has an edge over the other aspirants in the race for the AU job because of his experience. "Consistency has helped him. He has been consistent in fighting for human rights, the welfare of people, and for the lowly in the society," Mbadi says.
Nyatike MP Tom Odege says Raila has remained true to his call. "That's how he has gained the trust of many."
Awendo MP Walter Owino said: "Raila has a strong personality. He takes a stand and sticks to it. He has a reliable support base which has played a major role in his success."
[Additional reporting by Anne Atieno]