A self-taught artist, Poleskie had his first one-person show at the Everhart Museum, Scranton, Pennsylvania in 1958, while still in college.

After graduation Poleskie was employed briefly in Wilkes-Barre, Pennsylvania, as an insurance agent and commercial artist, before moving to Miami where he worked as a designer in a screen-printing shop.

Rather than join the ranks of the Abstract Expressionists, Poleskie enrolled in art classes at The New School with the figurative painter Raphael Soyer.

Involved in the New York art scene, Poleskie became friends with many of the artists and critics of the day including, Elaine and Willem de Kooning, Frank O'Hara, and Louise Nevelson.

During the five years he ran the operation the names of the artists who had prints made at Chiron Press reads like a who's who of the artists of the 60s and includes such figures as Robert Rauschenberg, Roy Lichtenstein, Andy Warhol, James Rosenquist, Alex Katz, Robert Motherwell, and Helen Frankenthaler.

In 1968, wanting more time to devote to his own art, Poleskie sold Chiron Press and accepted a teaching position at Cornell University in Ithaca, NY.

In his Aerial Theater performances Poleskie flew an aerobatic biplane, trailing smoke, through a series of maneuvers to create a four-dimensional design in the sky, e.g. in Hollywood/FL (1983), Richmond (1985),[1] Southampton (1989),[2] Clemson (1989).

Among the cities he has had his work shown, or done performances, are New York, Boston, Washington D. C., Los Angeles, San Francisco, Berkeley, Toledo, Richmond, Williamsburg, San Antonio, and Miami, in the USA; London, Southampton, Loughborough, and the Isle of Wight in the UK; Rome, Milan, Bologna, Brescia, Como, Trento, Turin, Verona, and Palermo in Italy; Munich, Stuttgart, and Kassel, in Germany; Linz in Austria; Ljubljana, Zagreb, and Belgrade, in the former Yugoslavia; Moscow and Saint Petersburg in Russia; Warsaw, Gdansk, and Lodz, in Poland; Tbilisi in the Republic of Georgia; Vilnius in Lithuania; Freetown in Sierra Leone; Stockholm in Sweden; Rio de Janeiro in Brazil; Tegucigalpa and San Pedro Sula in Honduras; Barcelona, Madrid, and Cadaque in Spain; Locarno in Switzerland; and Tokyo and Kyoto in Japan.