For the fourth time in 20 years, Mr Raila Odinga has failed to achieve his ultimate dream-- assuming the Presidency.
And what might make it even more painful is that he has been beaten for the second time in a row by the much younger rival he first under-rated as a walkover.
As President Uhuru Kenyatta embarks on a second term, the man who can rightfully claim credit for helping make it all possible through a lifelong struggle for democracy is looking at the prospects of bowing out with one unfulfilled ambition.
As he ponders his latest loss, Mr Odinga has to reconcile himself to the stark reality that at 72, he may never vie for the presidency again, unless a petition to the Supreme Court gives him another chance.
He entered the contest this year aware that this was a last-ditch effort with time not on his side.
And as part of the deal by which he secured presidential nomination for the National Super Alliance, the Orange Democratic Movement leader had to promise that win or lose, he would not offer himself for the presidency at the next elections in 2022.
This means that even had he beaten President Kenyatta and made it to State House, President Odinga would have served only one term and then handed over the baton to his deputy Kalonzo Musyoka.
And if he did not win, he would still step aside and let Mr Musyoka, the Wiper party leader, step up to the plate.
It should thus be certain that if he keeps to his word, Mr Odinga will be riding off into the sunset looking back whimsically, and maybe with a sense of betrayal, at what might have been.
Having lost twice to Mr Kenyatta might be particularly painful when he looks back not just at his own years of struggle and sacrifice, but to a generation before him.
Mr Odinga can rightfully say that he dedicated his life to the struggle that brought to an end the one-party Kanu dictatorship and gifted Kenyans the era of human rights and democracy that allowed them to vote in leaders of their choice.
When he was suffering detention, torture and exile for the cause, young Uhuru Kenyatta was enjoying the fruits of the dictatorial regime; and Mr Mwai Kibaki was infamously proclaiming that "a mugumo tree (read Kanu) cannot be cut down with a razor blade".
When the single-party edifice collapsed at the end of 1991, former Vice President Kibaki who had remained in Kanu through the struggle for democratisation, swiftly shifted to the opposition.
When the best opportunity presented itself in 2002 to uproot the monolith, it was Mr Odinga who destroyed Kanu from within.
He used a brief flirtation with the then ruling party to engineer a rebellion against outgoing President Daniel arap Moi's handpicked successor, Uhuru Kenyatta, and then led decamping troops into backing Kibaki's presidential candidacy under the united opposition banner.
That was the second time an Odinga had put aside his own and his community's aspirations to back a Kikuyu for president.
It started with Raila's father, Jaramogi Oginga Odinga, turning down entreaties to take up the leadership mantle at the dawn of independence in the early 1960s in favour of Uhuru's father, Mzee Jomo Kenyatta.
Freedom was attained in 1963 with Jomo Kenyatta as Prime Minister, eventually president, and Oginga Odinga as his deputy.
The Kikuyu-Luo alliance under Kanu lasted only three years as ideological differences drove Mr Odinga out of Kanu in 1966 to launch the Opposition Kenya Peoples Union.
He became the father of opposition politics and in 1969 was thrown into President Kenyatta's detention camps.
He was reduced to a political non-person even after release and remained shunted aside even after President Kenyatta died in 1978 to be succeeded by Daniel arap Moi.
His son and political heir, Raila, first came to public attention in 1982 when he was arrested and then detained without trial in the wake of an abortive military coup attempt.
He was released in 1988 but barely seven months later was consigned to a second stint in detention during the crackdown on Mwakenya and other alleged subversive underground groups.
He came out of detention camp in 1989, but one year later was put behind bars again as the Moi regime cracked down on the leaders behind the nascent campaign against the one-party dictatorship.
Mr Odinga's 'Kibaki Tosha' proclamation helped end the Kanu era and he came to occupy a prominent place in the new Kibaki administration.
Kanu's losing candidate, Mr Kenyatta took his own place as leader of the opposition.
The difficult marriage came to a halt in 2005 in the wake of a contested referendum on a new constitution.
Mr Odinga and many of the former Kanu leaders who had campaigned on the Orange symbol defeated the proposed constitution but were shut out of a reconstituted government.
In a strange twist of fate, Mr Kenyatta who was also in the Orange 'No' campaign switched sides and joined the Kibaki government, while his Kanu ally William Ruto remained in the Orange ranks.
Come the 2007 elections and Mr Odinga fought a strong presidential campaign on the Orange Democratic Movement flag.
Another notable candidate was Mr Kalonzo Musyoka of Wiper.
Mr Odinga lost by the narrowest of margins and the ensuing protests against what his supporters said was a stolen election quickly escalated into serious violence.
A negotiated settlement brokered by the African Union saw Mr Odinga installed as Prime Minister, sharing power with President Kibaki in a Government of National Unity.
His side of the coalition included Musalia Mudavadi as Deputy Prime Minister, and William Ruto as minister for Agriculture.
President Kibaki's side of the coalition included Mr Musyoka as Vice President and Uhuru Kenyatta as Deputy Prime Minister.
That was the coalition that in 2010 delivered on the promise of a new constitution, the crowning glory of the Kibaki-Odinga partnership.
But it was also a union riven by deep divisions, especially after Mr Kenyatta and Mr Ruto, who were on opposite sides of the 2007-2008 post-election violence, were indicted by the International Criminal Court to faces charges of crimes against humanity.
The 2013 elections approached with Mr Odinga almost a shoo-in for the presidency.
His camp thought the emergence of Mr Kenyatta and Mr Ruto as the main rivals would make for easy pickings.
In the first place, Mr Kenyatta and his running-mate William Ruto were facing serious criminal charges at the ICC and there was doubt whether they would be allowed to run at all.
Then there was the ethnic issue, the presumption being that Kenyatta-Ruto would not find favour when there was clamour for other communities to get a taste of power.
The assumption was that UhuRuto would not sell, especially when the ticket was led by not just another Kikuyu to succeed Kibaki, but a Kenyatta scion at that.
Raila Odinga expected a walk-over. That was the biggest miscalculation ever in the political life of a man always seen as a master strategist.
If losing to Mr Kenyatta the first time around hurt, the second loss must be utterly humiliating.
Looking back at what his father never attained and himself falling short, he might call it a case of historical injustice.
There would be consolation though, for the man walks into the sunset smug in the knowledge that his role in the history of Kenya can never be erased.
But the pain is that like the freedom fighters who sacrificed all so that Kenya could be free only to be shunted aside at independence, Mr Odinga fought dictatorship and endured jail and suffering, only to be denied the ultimate prize.
Four failed presidential bids will certainly be a blot on his legacy, especially in a society where the presidency is exulted to divine status.
Yet, being the politician the country has seen in the last two decades, it would be premature to write him off entirely.
He may never contest the presidency again but his capacity to pull strings from behind the scenes cannot be underrated.
Chances are that he will want the struggle to continue and if he is not leading from the front, he will be pushing from behind.
As leader of ODM he controls the biggest partner within the Nasa coalition and indeed one of the largest and best-established political parties in the country.
ODM will be looking for a successor to take up the mantle, as will the Luo community that presently has no heir-apparent.
Mr Odinga might also play a pivotal role in keeping Nasa together amidst also certain jostling for leadership between Mr Musyoka and Mr Mudavadi who will both be eyeing the 2022 ticket.
Outside local politics, Mr Odinga could easily take his place as a respected elder statesman on the African continent.
He prides himself as a Pan Africanist and on his travels across various African countries is often accorded treatment almost equal to a head of state.
After losing at the 2013 presidential elections, he announced the formation of a foundation dedicated to promoting fair trade practices between African countries and the developed nations, resolving conflicts, and promoting democracy on the continent.
An African elder statesman, Pan Africanist and internationalist would have no shortage of assignments as a special envoy, peacemaker and mediator for bodies such as the African Union and United Nations; and speaking tours on the global lecture circuit.