Eight years ago, Greece’s radical leftist Syriza party set out to change capitalism as we know it and nearly crashed the country out of Europe’s single currency.

Since 24 September, it is led by a former shipping asset player and Goldman Sachs trader.

Stefanos Kasselakis, 35, founder of shipping outfits Tiptree Marine, SwiftBulk and SwiftTanker, won a Syriza party member vote to become its chairman and thereby Greece’s opposition leader.

According to preliminary results, he garnered 57% of the vote, beating rival Effee Achtsioglou, 38 — a Syriza party insider and former labour minister.

“Comrades, today the light has won and our hope becomes the future,” Kasselakis said in a victory speech in Athens early on Monday.

Kasselakis earned a small fortune last year through opportunistic bulker and tanker asset plays.

After selling his ships, he entered the Syriza leadership race as a total outsider. A Greek expat from Miami, Kasselakis lacks prior political experience, including being a party member.

As the campaign progressed, however, the telegenic and social-media savvy Cretan attracted new members and coalesced with Syriza barons close to outgoing party chief Alexis Tsipras.

Tsipras, a former prime minister, resigned in July 2019 after Syriza lost three consecutive parliamentary elections.

Former Syriza leader and Greek prime minister Alexis Tsipras (right) and Stefanos Kasselakis. Photo: Stefanos Kasselakis via X

Kasselakis’ campaign combined populist anti-elite rhetoric with traditional progressive themes, such as the separation of church and state, the defence of LGBT rights and the abolition of mandatory military service.

Kasselakis became the first political leader in Greece to be openly gay. In his victory speech, he thanked his US-born partner for encouraging him to become politically active.

Successful but chequered history

While acknowledging his experience as a shipping entrepreneur, Kasselakis’ campaign did not dwell on the details of his investments.

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

Kasselakis was a Goldman Sachs commodities associate before he began touting the SwiftBulk project to investors in 2016.

Traditional Greek shipping player AM Nomikos was a minority shareholder in the venture, as well as a technical and commercial manager.

Philadelphia Coatings, a company founded by his father, Theodore Kasselakis, also came under the Tiptree corporate umbrella in a related transaction.

In the late 1990s, Theodore ran a marine coating business in Greece in which Stefanos or his other son Stelios was a minority shareholder.

The marine coating business, however, went belly up after a court found the company made false statements to a business partner.

After that setback, which Stefanos last month attributed to corrupt Greek justice, his family moved to the US, where he stayed since age 14.