However, his controversial public stands and complaints about his often 'uncommunistic' approaches saw Chakraborty failing to keep pace with his contemporaries in the CPI-M's hierarchy, despite over half a century of his association with the communist movement.
His organisational capability was noticed by legendary CPI-M leader Pramod Dasgupta. He was drafted into the state committee in 1971 alongside Buddhadeb Bhattacharjee and Biman Bose. Four years later, the late Anil Biswas was included.
But while the other three made it to the state secretariat and CPI-M central committee in the 1980s and subsequently to the politburo, Chakraborty got a berth in the state secretariat only last year. And that too after Jyoti Basu publicly demanded that Chakraborty be included in the central committee and state secretariat.
Known for his ability to mobilise the masses for CPI-M's mammoth rallies in the sprawling Brigade Parade Ground, Chakraborty was many a times entrusted with tough responsibilities which he carried out successfully.
An instance was the controversy following the death of a godman Balak Brahmachari in 1993 whose thousands of followers refused to cremate him saying he was still alive. Following a directive from Basu, Chakraborty carried out a bloodless mission along with the administration - he freed the body from the custody of the guru's followers and got it cremated.
Chakraborty boasted time and again: 'I have the ability to implement whatever I plan, except making a dead man alive.'
He also took on party bosses by coming out in support of former Lok Sabha speaker Somnath Chatterjee when the latter refused to resign from the post ahead of the July 2008 trust vote in parliament.
Chakraborty had said then: 'The post of speaker has its sanctity and is above party politics. Chatterjee was elected unanimously by the members of all political parties. The speaker's case should not be viewed as a CPI-M party affair.' That remark too invited censure from his party.