From his March 2018 handshake with former President Uhuru Kenyatta to the announcement of Ruto's win in the August 9 presidential election, the former Prime Minister had assumed what Ruto would call a "strange role".
It was during this period that many would say Raila had undergone a transformation of sorts, mellowing from the politician who consistently criticised Uhuru's policies, unearthed mega scandals in the government and offered an alternative voice, to one who played soft on the government in the face of damning scandals.
Raila was not in Uhuru's government but cooperated with the former president, and he would, on many occasions, say the new arrangement saw him offer more constructive criticism.
There was no need to shout, he would say, when it was possible to consult. In some way, he had become the president's quote-unquote advisor, and Uhuru would acknowledge he heeded Raila's advice in running government.
In the run-up to the August 9 election, Uhuru consistently said the handshake had granted him some breathing space, allowing him more time to deliver for Kenyans.
Scandals dogged Uhuru's regime in his second term as much as they did in his first, and his handshake with Raila had fallen short of being the magic wand that would put an end to the ills in government.
In the face of scandals, such as the Sh7 billion Kenya Medical Supplies Authority (Kemsa) saga, Raila did not hit as hard as he would, ordinarily. Neither did he call out the former president when he refused to appoint some 41 judges, against court orders. Raila's allies in Parliament took his cue.
A vacuum would emerge, but none, besides the civil society, seemed too eager to fill it. Ruto, then the Deputy President, would sporadically lash out at the president, as did his allies, but he was silent most of the time.
The President has referred to himself as the then Opposition leader, but he hardly was. Afraid of antagonising Uhuru's Mt Kenya base, Ruto played it safe in criticising his former boss. Further, he would credit Uhuru for the work he had done in a bid to tie himself to the former president's successes.
For the longest time, Ruto's allies in Parliament, despite falling out with the president, voted to endorse his policies in Parliament. Only much later did they reject his legislative proposals, such as his and Raila's joint push to amend the Constitution through the impugned Building Bridges Initiative (BBI).
And so, for a long spell in Uhuru's second term, there was not much opposition. His first term was different. Frustrated that the Opposition was becoming a nag, Uhuru would occasionally lash out, accusing Raila of failing to offer solutions.
"Backwardness! Backwardness! Pettiness! Pettiness!" the former president would describe Raila for his criticism in 2016. "Kazi yake ni 'Oh, pesa hii imeibiwa (He is preoccupied with claiming money has been stolen)'."
Back then, Uhuru and Raila engaged in frequent exchanges, which fell silent with their rapprochement. Over the last few weeks, such exchanges, now between Raila and Ruto, have made a comeback, with the president sending mixed signals on whether he prefers to have an Opposition in place. Since Ruto was sworn into office, the Opposition has kept him and his government busy responding to claims of budding a dictatorship, turning back on their promises, neglecting starving Kenyans and overburdening, among others.
Cost of unga
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During the campaigns, the President promised an immediate solution to the rising price of unga.
As the Supreme Court battle raged, Deputy President Rigathi Gachagua blamed Raila for the high cost of unga, saying the price would have been already dropped had the ODM leader not challenged Ruto's win.
Raila recently called out the government for going back on this promise and for seeking one year to bring about a drop in unga prices. His recent criticism of the government centred on Ruto's alleged witch-hunt against former Director of Criminal Investigations boss George Kinoti, proposal to increase taxes and statutory deductions as well as legalising the importation and cultivation of genetically modified organisms (GMO).
Raila is not the only one keeping the government on its toes. Wiper leader Kalonzo Musyoka has also been keeping Ruto busy, offering hard-hitting criticism on issues such as making unilateral decisions, saying that the president displayed early signs of an autocrat.
Narc Kenya leader Martha Karua has also kept the Opposition fire burning, launching scathing attacks against Ruto. In Parliament, Azimio lawmakers have faulted Ruto for appointing cabinet secretaries with tainted pasts, failing to achieve gender and regional balance in his appointments and for breaking his promise to have an equal number of male and female cabinet secretaries.
Opposition MPs had offered disclaimers even before Ruto took office. A day before Ruto was sworn in, Minority Leader Opiyo Wandayi had said they would "robustly check the government."
Wandayi yesterday said they would play their oversight role, warning that "Ruto and his team should not be jittery."
"We will keep them on their toes on every single issue and as we do so, we will remain objective," he said. "If they do something in the interest of the public, they will be doing their job and they should not expect us to clap. But if they go astray and give off the slightest indication that they are reneging on their promises, they should prepare for persistent and consistent reminders."
Any time soon
Wandayi said no negative will go unchallenged. "If they think we will reduce the pressure any time soon, they are in for a rude shock."
Completing the opposition line-up are civil society groups such as the Kenya Human Rights Commission (KHRC), which has opposed Ruto's nominees for Principal Secretaries, saying it favoured two communities at the exclusion of many others, as well as failing to meet the two-thirds gender threshold, among other issues.
Even though such a multi-pronged Opposition may lend more scrutiny, Parliament ultimately holds the key to keeping the government in check, given one of its principal roles is providing oversight to the Executive.
Kenya's presidential system deeply entrenches the principle of separation of powers, which each arm offering checks and balances to the other. Constitutional lawyer Bobby Mkangi says Kenya's setup offers "more buffers" in checking the Executive.
"Oversight comes easy because it comes in two ways - institutionally and politically ," he argues.
"Institutionally in the way the arms of government are constituted and with the presence of independent constitutional bodies that also play an oversight role. Parliament does not act, in the first instance, as political but is institutional.
"Politically because of the political formations that are represented in Parliament, which organise to counter the Executive." Being among the framers of the Constitution, Mkangi said it is important that Parliament stands together in checking the Executive.
"In the US which has the presidential system, there are times that the legislature has stood together to check the Executive, but it doesn't happen a lot these days," he adds, blaming the situation on the emerging personality-based politics cultivated by former President Donald Trump within the Republican Party, the kind that has existed in Kenya for decades. "We have not escaped the personality cults and we have seen the strong personalities take control of parties and institutions." But university lecturer Gitile Naituli argues that the previous parliamentary system fits Kenya better.
"We are too mature for a presidential system," Prof Naituli says.
"The presidential system works better in mature democracies where Parliament can stand with one voice. Uhuru captured Parliament and it is now in Ruto's pocket. The fact that MPs did not reject any of Cabinet nominees despite the dirt on some of them shows we cannot rely on Parliament."
Superior numbers
In Uhuru's first term, MPs from the minority side provided critical checks, flagging policies that threatened the rights and freedoms of Kenyans. Allies of the president supported him in the face of resistance, using their superior numbers to have their way in Parliament (The courts would reverse some unconstitutional laws passed by Parliament).
The Opposition voiced concerns, but that was all they could do. That could be true in Ruto's tenure, given his superior position in Parliament, commanding more MPs than Raila as a result of his raid on Azimio in the wake of his victory.
"Parliament needs to remember it is wananchi who put them in office and they should put the wananchi interest ahead of the party's and its leaders' interests," Mkangi says.
Prof Naituli argues for a revival of the civil society in providing the necessary checks.