Ruto met for the first time, and worked closely with Kalonzo Musyoka, then a minister and Kanu national organising secretary, under whose docket the women and youth affairs directorate was domiciled.
Today, Kalonzo is among the leading lights in the newly launched Movement for Defence of Democracy (MDD) -- a group composed of leaders who insist Ruto's Kenya Kwanza administration is illegitimate and should be ousted by mass protests.
At KICC, Ruto had a front row seat tutorial on political intrigues, lessons that seem to have served him well in his own rise to the top.
Dr Ojiambo recalls a lanky young fellow who was extremely humble and obedient. "He was obedient and patient. I would send him for mandazi and chips which we would have for lunch with black tea. He put up with it admirably for a young university graduate," she says.
Unknown to Ruto, Ojiambo explains, she would raise money to pay his salary, and run the office through writing conference papers for civil society groups.
In 1991, women and youth did not rank highly in the grand scheme of things in Kanu beyond dancing and entertaining politicians at public rallies.
The women and youth affairs department was not even a fully fledged secretariat of the party, but domiciled under the office of the National Organising Secretary.
Contrary to popular narratives that Ruto was key driver for the Youth For Kanu (YK'92), he was a junior youth winger.
"Ruto was not in the top leadership of the Youth for Kanu 1992, there were other senior players, but I was glad he came, and he has turned out the most consistent and successful of the lot," Ojiambo recalls.
Ruto's friends and foes agree he is an energetic political worker.
He also seemed to be extremely deft in being at the right place at the right time and making smart moves at critical moments, especially in picking allies to work with.
Among his contemporaries, the second evident characteristic of Ruto's political rise to the top is he is often underestimated by his rivals.
In all his defining political duels, Ruto has been deemed an underdog, going by public profiles and credentials of opponents.
However, it has since turned out either a clever tactic on his part, or a cruel flaw of assumption that blindsides his rivals.
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MDD is only the latest in a long series of contests for supremacy and legitimacy that is the nature of political battles.
The difference this time however being he wields Executive power as president and Commander-in-chief of the Kenya Defence Forces (KDF), while his adversaries are opposition activists who do not even hold elective office.
Ruto hit the headlines in 2004 when he publicly declared "Over our dead bodies!" to an application made by Nairobi constitutional and human rights lawyer Kamau Kuria, to compel former President Daniel Moi to testify in person at the Goldenberg Commission hearings at KICC.
Ruto's defiance against Dr Kuria's application came as a breath of fresh air and transformed him into an instant recognisable hero to the Kalenjin nation that was still smarting from the 2002 election loss.
However, the first real battle in which Ruto made his political bones was the fight for the Kanu machine, then headed by Moi in 2005.
Ruto did not count for much in the line-up for national positions, being eclipsed in resources and stature then by top Kanu princes Mutula Kilonzo, Bonaya Godana, Julius Sunkuli, Nicholas Biwott, Dalmas Otieno and the like.
Mutula was the front runner for the secretary general's position.
For many years, Kanu used "guided" democracy to fill positions through pre-agreed negotiations before NDC meetings at Kasarani.
For this reason, the delegates register, then in Sunkuli's custody, was a closely guarded party asset.
To date, it has never been clear how Ruto, then a backbencher representing Eldoret North constituency, managed to have his own list of Rift Valley delegates sneaked into Kasarani gymnasium to elect him secretary general.
This placed Ruto and Uhuru firmly in charge of then powerful Kanu machine, resources and networks, which they would exploit to give ODM victory in the November 2005 referendum campaigns.
It never was in dispute that while Raila Odinga provided the energy and street democratic credentials to the Orange Movement in the 2005 referendum, the Orange (NO) campaign rode largely on the Kanu organisational capacity and national wide networks.
Buoyed by the victory at the referendum, Ruto for the first time in 2006 felt confident enough to declare he would run for the highest office in the land the following year, 2007.
Many did not take him seriously, dismissing the declaration as a youthful adrenalin-loaded ego trip.
Ezekiel Barng'etuny then a veteran of Rift Valley and Kalenjin politics, who died in December of 2013, dismissed Ruto as punching above his weight like the Biblical Herod's daughter.
"After dancing brilliantly at the referendum, Ruto is asking for the ultimate price," the old man scoffed.
It is this disdain that seemed to have convinced Ruto the elderly and wealthy power men in Kalenjin land would never allow him rise above Eldoret North MP, upon which he switched loyalty to Raila Odinga in the 2007 elections.
This decision landed him a post as Minister for Agriculture in 2008, from where he was able to consolidate his position as the undisputed Kalenjin kingpin. The position of kingpin made him the target of intense courting by former President Mwai Kibaki and his handlers, and which firmly placed Ruto inside the Kibaki succession inner lane.
This involved pairing him with Uhuru Kenyatta to form the formidable Jubilee Alliance. With ICC cases hanging over their heads, it meant burying the hatchet to bring their warring Kikuyu and Kalenjin communities together for numerical strength.
In 2022, he beat the odd that were stacked against, including state machinery. It remains to be seen what tactics Ruto will conjure up to deal with MDD which has planned a grand protest in Nairobi today.