His allies and past critics believe that it is finally his time to also enjoy the fruits of boardroom negotiations that shaped him to be a kingmaker in the country's politics.
This is after the African Union (AU) Executive Council dropped two key proposals that would have locked out Raila's candidature for the Commission (AUC) chairperson seat.
The boardroom negotiation by the council has also proposed that the next chairperson come from East Africa, which increases Raila's chances of ascending to the African throne.
In his decades-long political career, the ODM chief has relied on negotiated democracy to build the careers of his allies even as his own political interests flickered in the flames of defeat.
Among the beneficiaries of his boardroom negotiations include past presidents, governors, MPs, senators, and woman representatives in areas perceived to be his strongholds.
Leaders from minority tribes have also been among the greatest beneficiaries in Nyanza, Coast and Western regions.
In 2002, Raila was at the forefront of brokering a power formula that helped former President Mwai Kibaki to clinch the presidency with ease.
He led spirited campaigns against former Kanu leader Uhuru Kenyatta who was making his first stab at the presidency.
His "Kibaki Tosha" clarion call in 2002 came as a surprise to many of his supporters but guaranteed a united Kenya and an emphatic Narc win.
"Any subsequent endorsement of Raila has been payback for his selflessness for the Kibaki declaration and his steadfastness in the struggle for good leadership," says Rongo MP Paul Abuor.
He believes that if Riala bags the AUC chair, the biggest beneficiary will be Africa which "will be having one of their great sons who has an impeccable record of fighting for democracy and good governance at the helm of its leadership."
After Raila pushed for the formation of the Narc coalition - one of the country's most formidable alliances in history - his supporters were hopeful that the negotiated democracy he had brokered in favour of Kibaki would be rewarded with a Memorandum of Understanding.
This was, however, never going to be and he soon fell out with Kibaki's administration.
According to his allies, Raila's commitment to resolving issues through boardroom talks has helped calm tensions and achieve his goals seamlessly.
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In his own ODM camp, negotiated democracy has been a focal point of Raila's political influence and has helped most of his allies win seats without a sweat.
The deals have been anchored on clan, geographical locations, gender, and popularity but always attract criticisms from opponents who believe the direct nomination by ODM is always entangled with underhand dealings.
ODM Chairman John Mbadi says sometimes, this negotiated democracy brings out the best out of the flock in terms of quality.
According to Mbadi, where negotiation is involved, people go for those who have the capacity and chance of winning.
"That demonstrates that Raila has some qualities which stand out when people just appreciate and agree on whom to benefit or to support... Contrary to what people say about Raila, he is a team player," Mbadi explains.
He believes Raila is one person, apart from his father, to have voluntarily removed himself from a presidential race in 2002.
While some beneficiaries of the boardroom power-sharing deals have managed to effortlessly win seats, especially in Nyanza, Western, and Coast, some disgruntled parties have always jumped ship to support Raila's opponents.
For instance, in the build-up to the 2022 General Election, Raila's ODM house was on the verge of cracking as key allies eyed the same seats and engaged in spirited campaigns against each other.
In Homa Bay, Mbadi, former Kasipul MP Oyugi Magwanga, former County Secretary Isaiah Ogwe, Gladys Wanga, and former Nairobi Governor Evans Kidero were all eyeing the ODM ticket to contest Homa Bay governorship.
So fierce was the competition that there were fears the party primaries risked splitting the party.
However, Raila moved to address the situation by using negotiated democracy by convening a meeting with leaders to broker a deal.
Through the move, Raila convinced his allies to drop their bids in favour of Wanga, which consequently allowed her to become the first female governor in Nyanza.
Magwanga also became a key beneficiary of the deal and was selected to deputise Wanga, effectively blowing out the flames of animosity that had existed between the two leaders during campaigns.
The decision, however, did not augur well with Kidero, who jumped ship and joined President William Ruto's Kenya Kwanza and has been a critic of ODM since.
Similarly, in Kakamega, Raila's negotiated democracy also saw current Deputy Governor Ayub Savula drop his interest in the governorship to back Fernandes Barasa for the governorship.
In Migori, Raila has always brokered power through democracy and ensured that the Kuria community clinches key seats in the county. In the three elections, deputy governors have always been selected from the community.
A similar development also took place in the race for Nairobi governorship where Raila's party managed to convince Westlands MP Tim Wanyonyi to drop his bid and back Jubilee candidate Polycap Igathe.
Although Igathe failed in his mission and lost to Kenya Kwanza's Johnson Sakaja , the boardroom deal that helped unveil him as a candidate demonstrates Raila's character as a kingmaker.
And after several years of playing the kingmaker role for his allies, the stars appear to have aligned for the ODM chief after key continental players threw their weight behind his AUC bid.
Today, Raila appears to be on track to enjoy the benefits of boardroom negotiations as the Kenya Kwanza government also prepares an intense campaign war chest to help him clinch the AU seat.
President William Ruto has crafted a team of elites to help Raila marshal support across the continent. The team is led by Prime Cabinet Secretary Musalia Mudavadi.
Last month, the president announced that the East Africa bloc has agreed to produce one candidate. He expressed confidence that Raila will clinch the seat.
Post-election scenarios
Communication strategist Dr Barack Muluka says Raila has been involved in a number of negotiated post-election scenarios and dispensations that have led to working with the governments of presidents Moi, Kibaki and Uhuru.
He says that in each of those cases, he has arrived from the position of the party that has been wronged, the perception has been that he has been cheated out of an election victory.
"Clearly the most obvious beneficiaries have been the three presidents, as they have enjoyed the calm and numbers that they need to the power and benefits of the highest office in the land and the opportunity to govern comfortably," Dr Muluka says.
He opines that Raila has only benefited marginally, by enjoying some status of sorts, either in government or around government.
According to Muluka, the downside of this has been the slowing down of the push toward the realisation of a proper democracy in Kenya.
Constitutional lawyer Bruce Odeny believes that Raila picked the negotiated democracy from his late father Jaramogi.