Nairobi Governor Mike Mbuvi Sonko will spend two more nights in police custody following charges on Monday with 19 corruption-related offences.
The flashy governor and his co-accused faced 19 charges of corruption, abuse of office and irregular payments that saw the county lose Sh357 million.
They denied the charges and applied to be freed either on bond or cash bail, amid strong opposition by the prosecution.
Chief magistrate Douglas Ogoti said he will give his ruling on December 11.
The magistrate also directed prison authorities to confirm claims that Mr Sonko was sick through an examination in the presence of his doctor.
Mr Sonko, who spent the weekend in custody, denied charges including money laundering, conflict of interest, abuse of office, acquisition of public funds and conspiracy to commit an economic crime.
Through more than 12 advocates including legislators, he pleaded to be released on bond.
Mr Sonko was accused of corruptly receiving more than Sh25 million, through proxies including Mr Fredrick Odhiambo alias Fred Oyugi of Yiro Enterprises, who also denied the charges.
The money was allegedly deposited into the county chief's personal accounts in different banks around the country.
In the first file, Mr Sonko was charged alongside Mr Odhiambo, Mr Anthony Otieno Ombok, Web Tribe Limited and its director Danson Muchemi, Robert Muriithi, and agent Zablon Onyango.
Mr Muchemi, Mr Muriithi and Mr Onyango were not in court but their lawyer informed Chief Magistrate Ogoti that they presented themselves to the offices of the Ethics and Anti-Corruption Commission (EACC) as directed.
They were jointly accused of embezzling Sh24,100,000 from the county through a tender for an electronic revenue collection and payment system.
They allegedly committed the offence between July 1, 2018 and January 31.
The prosecution, led by State counsel James Kihara, pleaded with the court to deny Mr Sonko release, saying he was likely to interfere with investigations or intimidate witnesses - junior officers in the county.
Mr Kihara described Mr Sonko as a "flamboyant, influential and wealthy public figure, with a rowdy and sycophantic following", and who has, on several occasions, "threatened and demonstrated acts outside the law".
He further said the governor incited county executive committee members against recording statements on the investigation so releasing him would be jeopardising.
The prosecutor also noted that Mr Sonko was arrested in Voi town on Friday while attempting to flee the country, "a clear manifestation that he is a flight risk".
The governor was also accused of obstructing police and in the process, injuring one of them.
Mr Kihara further told the court that Mr Sonko was convicted on March 12, 1998, after failing to appear in court for the hearing of two criminal charges.
He said Mr Sonko was at the time sentenced to six months in prison for each of the two cases, with the alternative of paying a fine of Sh500,000.
The prosecutor pointed out that the convict fled from custody after he was admitted at Coast Provincial General Hospital on April 16, 1998, so a signal was issued from Shimo la Tewa prison.
He added that the governor had pending criminal cases in Mombasa, where he was charged with seven counts, and that despite being granted anticipatory bail, he was yet to present himself before the magistrate there for plea-taking.
The prosecutor further said a warrant for his arrest was issued and was still in force.
For the rest of the accused persons, Mr Kihara urged the court to consider the money involved and to bar the public officials from accessing their offices.
He also asked Mr Ogoti to direct them to submit their passports to the court.
Through lawyer Cecil Miller, Mr Sonko claimed he was assaulted during his arrest and that he was experiencing chest pains.
Mr Miller said a doctor who examined his client at the EACC cells where he was held recommended a CT scan. He explained that another doctor who was sent by the commission agreed.
The lawyer pleaded with the court to release his client, claiming his life was at risk.
He dismissed claims that the governor was a flight risk and said he was arrested while going about his business, on his way to Mombasa.