Book cover for “De groote Olie octopus, door Truth onderzocht” (The Great Oil Octopus by Truth Examined)‎. ‎Amsterdam, L.J. Veen. Conflicting dates: first published 1910, reprinted 1925?

Dutch Anti-trust/Anti-capitalism criticising oil companies including Esso and Rockefeller.

References: Antiqbook, http://www.antiqbook.nl/boox/vvliet/12028.shtml 
Image Source: International Institute of Social History, Collection: IISG, Call # BG C12/589. (Accessed: 23rd Oct, 2010)

Courtesy of a dismissive article¹ on a protest outside the Ritz-Carlton hotel on March 9th 2010²: The Return of the Vampiric Octopus Squid. Giant red vampire squid used to depict the “blood-sucking aspect of trying to make profit … out of people getting sick”¹

And then there was the guy dressed up as what looked to me like, well, a Giant Red Squid of Death. The man in a black bodysuit with a red paper mache monster growing from his shoulders called it “a vampire squid.” His get-up, he said, was meant to dramatize the profit motive of publicly traded health insurers.

Thanks to hectocotyli for pointing this one out.

Footnotes

1. “Never underestimate the power of a lovely spring day in the nation’s capital to fuel a vigorous political demonstration.”
2. Audio recording in: Julie Rovner (2010) Protesters, Including ‘Vampire Squid,’ Picket Health Insurers’ Confab - Shots - Health News Blog : NPR (Accessed: March 16th 2010). 
3. Julie Rovner (2010) ‘Protesters … ‘

Image Source: Protesters, Including ‘Vampire Squid,’ Picket Health Insurers’ Confab - Shots - Health News Blog : NPR