"From early Soviet times down to the present day, we have seen enshrined in song and story a mythical world of old Odessa—a place that summons up images of a freer, more irreverent world filled with sunshine and possibility," stated Roshanna P. Sylvester, Associate Professor of History, DePaul University, at a 24 April 2006 Kennan Institute talk. Sylvester discussed her recent book Tales of Old Odessa: Crime and Civility in a City of Thieves, in which she uses articles from Odessa newspapers and periodicals to paint a picture of the people and culture that gave rise to these enduring myths about the city.

In Russian and Soviet popular imagination, Odessa is known for humor and lightheartedness, but also for subversion and criminality. "As with Chicagoans of the Capone era…the reputations of city and residents alike were closely tied to visions of regularized businesslike criminality," Sylvester said. The celebration of the antics of successful criminals, particularly those "who perpetuated their arts with a wink and a smile," was an important aspect of Odessan popular culture. Sylvester analyzed popular journalism—particularly articles relating to crime—from the first two decades of the 20th century, in order to better understand how Odessans of that period viewed themselves and their city, and how they related to modernity.

"Like their contemporaries in other cities, Odessans grappled with contradictions and anxieties that emerged with modernity, even as they reveled in the possibilities and delights offered up by their metropolis," Sylvester explained. While sharing many commonalities with other cities, Odessa has a specific geographic, historic, and demographic context that played an important role in shaping the unique ways in which Odessans approached modernity.

Founded in 1794 to exploit commercial development on the Black Sea, Odessa has historically oriented itself toward the outside world rather than toward St. Petersburg or Moscow, Sylvester said. She added that Odessa—in spite of a history that includes incidences of ethnic violence—was a diverse, cosmopolitan city. Until the first World War, the city was divided into three roughly equal groups—Russians, Jews, and everyone else. With no clear ethnic majority, social class became the primary marker of individual identity, and a middle-class, secularized Jewish culture "in a very real sense became the dominant culture of Odessa."

Stories in the popular press paint a vivid picture of the distinctive culture of late Imperial Odessa, highlighting the values, fears, and amusements of local citizens. Mainstream journalists, according to Sylvester, were preoccupied with the idea of intelligentnost', a term that synthesized Western middle-class notions of propriety and correctness and the Russian intellegentsia's "disdain for the self-absorbed individualism and concomitant moral lassitude of the bourgeois order."

Journalists' views of themselves as guardians of propriety did not prevent them from covering the sensationalist tales of crime and scandal that were popular among readers. "Newspaper stories revealed a fascination with the inauthentic," Sylvester argued. Journalists displayed both amusement and horror at stories of apparently respectable citizens committing immoral or criminal acts and sought to warn their readers of this potential danger of urban life. Likewise, they were troubled by the plight of people living in the urban slums who were intelligentnyi in character but not in outward appearance.

In 1914, an elephant living in an Odessa menagerie mauled his trainer, sparking an intense debate over what had gone wrong with the elephant, and how to deal with him. Sylvester argued that the story of Iambo the elephant became the basis for a civic epic in Odessa, with many different journalists using Iambo's story to further their own political, cultural, and moral agendas. She explained that articles about Iambo expressed concerns over the repressive state, the corrupting influence of materialism and urban life, and the commodification of identity. Portrayals of Iambo varied from an intelligentnyi elephant, to the leader of a revolutionary movement, to a lovesick youth lost in the modern city. Sylvester noted that when Iambo was eventually executed by a firing squad, Odessa papers carried glowing eulogies of the elephant and harsh condemnations of the members of the firing squad. "Iambo was a sacrifice on the altar of the city and culture, his death symbolizing the distance between the ideals and reality of Odessan civilization," she concluded.

The devastation of two World Wars and the Russian Revolution brought dramatic changes to the city of Odessa. According to Sylvester, by 1916, mainstream newspapers were expressing a distrust of foreigners and other strangers that only a few years earlier would have been entirely antithetical to the Odessan identity. The Revolution and Civil War decimated the city's vibrant middle class, and by the end of World War II, there were very few Jews left in the city. Nevertheless, the traditional image of Odessa lived on in the popular imagination of Russians and Ukrainians. "Now, in post-Soviet times," Sylvester concluded, "Odessans draw on popular images of their city's storied past to rekindle the mood of old Odessa and assert a powerful local identity."