Dragasakis was first elected as a Member of the Hellenic Parliament (MP) in 1989 for the Coalition of the Left of Movements and Ecology, in the constituency of Chania.

In March 2015, Dragasakis co-authored an article in the Financial Times with Yanis Varoufakis and Euclid Tsakalotos that asked Greece's creditors to give them a chance.

[7] After Yanis Varoufakis, the Minister of Finance, resigned on 6 July, Dragasakis was named as a potential successor.

[2] Friends have described him as "rigid and inflexible in terms of socialist perspective", but also tactical as he "the realism of everyday life".

[6] According to Stathis Kouvelakis, former Syriza spokesperson, Dragasakis is widely considered to have strong personal relationships with the Greek bankers,[9] going back to his early career.