Piterman was born in Odessa, Ukraine, Soviet Union. At the age of 12 his family emigrated to the United States, settling in California where he attended college at Berkeley, excelling in sports – including triple jump, later narrowly failing qualification for the 1992 Summer Olympics in Barcelona.
Having already quit sports, Piterman, now a real estate agent, relocated to Spain in 1991, immediately buying two football clubs: amateurs Tossa Sport and fourth division side Palamós CF, with the latter promoting to the third level under his ownership in 2002. Three years earlier he had been elected club president, and had his first hand at coaching in spite of not being qualified to do so.
In January 2003, while still president at Palamós, Piterman bought 24% of Racing de Santander's shares, thus reaching La Liga. He insisted on being his team's manager, which granted him disciplinary action from the Royal Spanish Football Federation for being in the technical area, which he sometimes eluded by being accredited as a journalist or photographer. Chuchi Cos, who had worked with him in Palamós, was also appointed manager during the Cantabria period; former club coach Manuel Preciado said of the experience with the businessman: "I moved into my dream home but a pigeon flew by and shat on my roof".
After a brief spell in handball, also in Cantabria, Piterman bought Deportivo Alavés, helping it return to the top flight in his first season, with Cos now acting as director of football. The American's spell in the Basque Country was also a rocky one, with three coaches being used during the 2005–06 campaign, which ended in relegation, the dismissals occurring when the managers refused to accept his interferences and impositions. Clashes also occurred with the club's players and fans alike. Piterman left a debt in the Alavés of more than 25 million Euros (35 million USD), and fled the country leaving the team on the verge of bankruptcy.
The pair Cos/Piterman appeared in 126 matches in Spanish football, winning 63, drawing 29 and losing 34. In 2006, Pietrman purchased a USL First Division franchise in San Francisco, California, the California Victory; it folded in one year, after he had already sold 51% of Alavés.
- El hombre de las mil caras (The man of a thousand faces); El Periódico Mediterráneo, 2 December 2002 (in Spanish)
- Funny old round-up; BBC Sport, 30 January 2003
- Manolo Preciado earns the plaudits, but Real Madrid take the points; The Guardian, 15 November 2010
- Piterman se carga a Juan Carlos Oliva por "insubordinación" (Piterman ousts Juan Carlos Oliva for "insubordination"); 20 Minutos, 16 February 2006 (in Spanish)
- Carreras denuncia el "trato vejatorio" de Piterman (Carreras denounces "vexatious treatment" by Piterman); 20 Minutos, 1 December 2006 (in Spanish)
- Piterman llama gordo y borracho a Óscar Téllez (Piterman calls Óscar Tellez fat and drunkard); Diario AS, 17 May 2006 (in Spanish)
- Dimitri Piterman llama "subnormales" a los aficionados del Alavés (Dimitri Piterman calls Alavés' fans "morons"); 20 Minutos, 22 February 2006 (in Spanish)
- La deuda del Alavés es de casi 28 millones de euros (Alavés almost 28 million euros in debt); Marca, 11 December 2007 (in Spanish)
- Whitecaps soccer league loses team; Canada.com, 20 November 2007