His involvement in a 2010 deal to privatize the state-run Iron Sleepers Company, Georgia's only railroad tie factory, led to his arrest twice in 2013, although the case made by prosecutors has been assessed by civil society organizations as having been politically-motivated due to his affiliation with the United National Movement.

Originally a small business using a few brewing pots,[3] it grew to become one of the leading beer providers in Georgia in the 1990s and became a limited company with Chocheli as the sole director in 1997.

In 1999, a controversial financial investigation that has been attributed by a corrupt maneuver within the administration of President Eduard Shevardnadze led to the closure of Lomisa's operations for six months.

[6] Two years later, his brother Iago would purchase the media channel Telecompany Georgia,[7] which would be contracted by the Ministry of Defense to diffuse patriotic programs, before being sold to Tamar Chergoleishvili, a journalist and wife of NSC Secretary Giga Bokeria.

[11] The large majority of Chocheli's private sector projects have been based in Shida Kartli and Mtskheta-Mtianeti, the regions making up the central part of Georgia and under economic pressure linked with the Russian occupation of South Ossetia.

[13] Tsezar Chocheli's political career has been closely associated with Akhalgori, his hometown in the Mtskheta-Mtianeti region that has been since 2008 under the control of the Russian-backed South Ossetia separatist republic.

The Rose Revolution, which led to the overthrow of Shevardnadze and the rise to power of Mikheil Saakashvili, was caused to allegations of massive voter fraud in the polls and most of the results were eventually cancelled by the Constitutional Court.

On 19 February 2008, Tsezar Chocheli resigned his parliamentary seat and was appointed as Governor of Mtskheta-Mtianeti by President Saakashvili to replace Vasil Maghlapheridze,[14] who had recently left office and joined the opposition.

In October 2009, Chocheli was one of the main negotiators of Georgia during a hostage crisis that saw Russian forces kidnap 21 Georgian citizens for allegedly crossing the conflict line.

[15] As Governor, Tsezar Chocheli oversaw several infrastructure projects organized by the central government meant to link the mountain zones of Khevsureti and Pshavi to the rest of the country,[16] while implementing the USAID's New Economic Opportunities program, aimed at funding small businesses along the administrative boundary line.

[4] Politically, he was closely allied with Saakashvili's United National Movement, while supporting the election of several UNM municipal assemblymen, such as Dusheti's Zurab Otiashvili,[18] and both him and his family's companies regularly donated to the party.

[20] Tsezar Chocheli resigned from office on 24 November 2012, shortly after the loss of UNM in that year's parliamentary elections that saw the victory of Georgian Dream, while the new government started legal proceedings against him.

Tsezar Chocheli became the subject of an investigation by the Ministry of Justice in December 2012 as part of a largest inquiry into an alleged attempt to bankrupt through predatory practices Cartu Bank, a lending organization belonging to Bidzina Ivanishvili, the founder of the new ruling Georgian Dream party and Prime Minister since October.

The case was controversial, former Prime Minister and UNM Secretary General Vano Merabishvili calling it "politically-motivated", and Chocheli denied all charges, claiming that the new authorities were launching a "war on business".

According to prosecutors, who sought a 12-year prison sentence, Chocheli and Giorgadze conspired toward fraud when hiking railroad tie prices after purchasing the company following the latter's win of a competitive bid, leading to an alleged 12 million-lari overcharge.

[38] In August 2020, Chocheli founded the Progress and Freedom Party (P&F) with Kakha Okriashvili, a fellow businessman serving as an MP from Georgian Dream.

[46] During the political crisis that ensued after the arrest of UNM Chairman Nika Melia in February 2021, Chocheli visited him in prison,[47] while he praised the service of former Prime Minister Giorgi Gakharia when the latter resigned, in contrast with other members of his party.