Should that happen, then the former Independent Electoral and Boundaries Commission (IEBC) boss will be following in the footsteps of former Chief Justice Zacchaeus Chesoni.
Chesoni served as the chairman of the Electoral Commission of Kenya (ECK) before it was renamed.
In December 1997, President Daniel arap Moi , a leader many pundits consider to be Ruto's mentor because of their hands on and authoritarian leadership, appointed Chesoni Chief Justice.
The soft-spoken Chief Justice, whose name was as much maligned by the opposition as Chebukati's because of alleged mismanagement of presidential polls, replaced Justice Abdul Majjid Cockar who retired on attaining the mandatory retirement age of 74.
Chesoni had been declared bankrupt and was said to have been spending most of his time in Casinos after serving as the Director of Land Adjudication before Moi appointed him judge.
"He was rehabilitated from his gambling appetite and made ECK chairman and then Moi elevated him to Chief Justice," says political analysts Martin Andati.
Drawing parallels with how Ruto is handling the Judiciary, Andati argues that Moi was also keen on having loyalists and that is why Chebukati fits the bill in the current scheme of things.
The analyst also thinks the government is in the process of taking away some of Attorney General Justin Muturi's, the way Moi did with Justice Mathew Guy Muli's office when he was the AG and later moved him to the Court of Appeal.
"The same thing Moi was doing is what William wants because the aim is to have a compliant Judiciary by using all means to ensure that they have people who can play ball, listen and do what you want," says Andati. And because the Kenya Kwanza leadership has since the last elections defended Chebukati from attacks by the opposition, it proves that he can be a loyalist.
Like Chesoni, Chebukati comes across as a slow and harmless public servant but underneath is a rigid and calculative player who held on to his position from 2017 despite mounting pressure from the opposition.
In 2017, Raila-led National Super Alliance (NASA) organised protests around IEBC offices at Anniversary Towers with protesters chanting "Chiloba must go".
ODM leader Raila Odinga. [Emmanuel Wanson, Standard]
Raila's allegations were supported by some political analysts who earlier this week told The Standard that the plan to appoint Chebukati to the appellate court has been in the pipeline for a while now.
"They agreed that the names of five High Court judges and two Court of Appeal judges will be forwarded by Ruto to JSC and that is when he proposed Chebukati and Hassan to be appointed as Court of Appeal judges, with Chebukati being later elevated to Chief Justice before the 2027 General Election," Raila said a week ago.
The allegations took another twist when Prime Cabinet Secretary Musalia Mudavadi waded into the debate, telling off Raila.
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Mudavadi, however, said that Chebukati has a right to apply for the Chief Justice post should he wish to because he is qualified.
Opposition leaders argue that because of the Supreme Court ruling of 2017 that reprimanded the electoral commissioners, Chebukati is not fit to be the Chief Justice.
Vihiga Senator Godfrey Osotsi pointed out that the 2017 Supreme Court ruling raised a lot of questions on how IEBC managed the elections.
He added that a Public Accounts Committee (PAC) report in Parliament also raised a lot of questions on how money was spent in procurement processes of that election.
IEBC was formed in 2011 after the enactment of the new Constitution to cure electoral ills witnessed when ECK officials were appointed by the president.
Lawyer Ahmed Issack Hassan was the first IEBC chair before he was forced to resign after opposition protests. He was succeeded by Chebukati in 2016.
The country is currently in the process of trying to reform IEBC.
A recently released report prepared by the National Dialogue Committee, co-chaired by Wiper leader Kalonzo Musyoka and Leader of Majority Kimani Ichung'wah, has given a raft of recommendations to bring changes in the electoral body.