It would likely be much, much easier for him to simply fly to Toronto and enter Canada on his Canadian passport (is he dual nationality with Canada and Russia both?). As a Canadian passport holder, he would simply be returning where he has citizenship / residency and no visa would be required.
Then, if he wanted to visit NYC, take a bus trip or flight as a tourist with an entry and exit ticket for the USA.
The reason I suggest that route that is that he
may require a US-issued visa to enter the USA from Venezuela and US Consulates generally do not look favorably on one-way tickets for those who apply for
tourist visas. Venezuela origin just makes that a bit worse, since the US and Venezuelan governments have been at odds. Venezuela origin and Russian citizenship with a Canadian passport.... well, it's getting more complicated.
Normally, a Canadian
citizen entering the USA directly from Canada or another country would not require a visa, but originating flights of foreigners from Venezuela will likely receive extra scrutiny. And is he a Canadian citizen or how is he a passport holder? Since you did not state his exact residency / citizenship status regarding Canada & Russia, that's about as much as can be said.
A bit more
information here.
As mentioned,
it can be complicated:
Quote: Residents (PR) of Canada who are landed immigrants generally need a passport and visa to enter the United States, unless they are a citizen of a country eligible for the Visa Waiver Program (VWP). If they are a citizen of a country eligible for the VWP, they are only required to have their valid passport - coming by land.
If coming by air and sea, they will need to have advance approval to travel through the Electronic System for Travel Authorization (ESTA System). There is an ESTA application fee of $14. To obtain a list of countries eligible for the VWP, please reference the Department of State Web site.
To find out if he will need a visa for his travel-through in the USA, he should contact the
US Consulate or Embassy in Venezuela.