Stefanos Kasselakis, a 35-year-old Greek ship investor who earned a small fortune through opportunistic bulker and tanker asset plays last year, has embarked on a political career with his home country’s main opposition party.

The formerly radical and now centre-left Syriza party held power in Greece between 2015 and 2019 but was trounced in two consecutive parliamentary elections since.

Its latest disastrous result in June sent the party in a tailspin, with former leader and then prime minister Alexis Tsipras quitting active politics and opening the field to a group of lesser-known hopefuls keen to replace him in a leadership election due next month.

Kasselakis, a Miami resident who was not even a Syriza party member and unsuccessfully stood for parliament on the party’s expat ballot list, publicly declared his candidacy early on 29 August.

“Enough generations were lost. It’s time to build the Greek Dream we all so badly need,” he said in a social media post.

Kasselakis is highly unlikely to win. Being a newcomer to Syriza, he lacks the party-political credentials usually required to promote him to the rank and file.

His social media campaign to “reconstitute a modern Left”, however, has caught on well with the wider public.

Kasselakis’ account was trending on X, previously known as Twitter, on 28 August in Greece.

In the morning of the same day, TradeWinds readers keen to find out more about him propelled a 2022 story about SwiftBulk to the top of our most-read articles list.

Greek shipowners are predominantly conservative.

Shipowner scions, however, have dabbled in Greek politics before — most famously Andreas Embiricos, a standard bearer of Greek communism, surrealism and psychoanalysis in the interwar years.

The social media campaign of the telegenic, boyish-looking Kasselakis has focused on traditional-left themes, such as the separation of church and state, the defence of LGBT rights, as well as the abolition of mandatory military service.

When wildfires raged on the island of Rhodes at the end of July, Kasselakis rushed to the area with his life partner Tyler McBeth to display solidarity with residents.

Other elements in his platform, however, such as his support for public-private partnerships to breathe some life into Greece’s notoriously stodgy state universities, may sit more oddly with orthodox-left voters.

While acknowledging his activity as a shipping entrepreneur, Kasselakis has not been highlighting details of his investment in Tiptree Marine, SwiftBulk and SwiftTanker — entities currently without ships.

While successful, the three vehicles did not escape the odd legal trouble shipping investors have often to contend with, such as compensation demands for US investment bankers and an entanglement in a “magic pipe” affair that briefly pitted Tiptree against V.Ships Norway.

It remains to be seen whether Kasselakis’ asset-playing skills of entering a market when it is low and exiting it when it is high will be transferable to politics.