Chettri, an MLA from Kalimpong constituency and a senior leader of the GJM which is spearheading the Gorkhaland statehood demand, met Trinamool Congress' All India general secretary Mukul Roy last night.
A source close to Chettri confirmed the meeting, but refused to divulge details.
However, secretary general of GJM Roshan Giri said the party had not sent Chettri to the state capital and he didn't think that the party MLA had met TMC leadership.
Asked about Chettri meeting Roy, Giri retorted, "what is wrong if he has met him".
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Chettri, is a highly regarded leader in the Hills and part of Bimal Gurung-led GJM's think tank.
The GJM has three MLAs from the three Hill constituencies in the West Bengal Assembly.
The meeting comes ahead of the Trinamool Congress supremo Mamata Banerjee's political convention in Darjeeling on October 24, when a sizeable number of people from the Hills are likely to join the ruling party.
The GJM, under pressure after the West Bengal government's crackdown on its agitation in demand of a separate Gorkhaland and a lukewarm response from the Centre, has already softened its stance and decided that its legislators would meet Banerjee during her visit to the Hills.
The agenda of the meeting would be the large-scale arrests of members of the GJM and Gorkhaland Territorial Administration (GTA), according to sources.
Altogether 1,300 people, including 13 members of GTA and some traders and businessmen allegedly funding the agitation, have been arrested so far in the Hills.