A $250 Two-Day Trip to New York: Why an 8.5% Chance Was Worth the Hustle

How a strategic mix of credit card credits and airline points turned a high-stakes NHL lottery trip into a $250 masterclass in travel hacking.

One of the best things about working for yourself is that you don’t need to pitch a “business cost” for a trip you find meaningful. With the NHL lottery set for May 5, I knew interest would be at an all-time high given what was at stake for the Toronto Maple Leafs.

Entering the draw with just an 8.5% chance, the Leafs actually faced a higher probability of losing their first-round draft pick entirely. Had they fallen out of the top five, the pick would have been given to the Boston Bruins—a condition of the deal that brought veteran defenseman Brandon Carlo to Toronto.

Despite the odds, I wanted to be there. The draw was held at the NHL Network studio in Secaucus, New Jersey. For a traditional employee, a last-minute request for a round-trip flight and hotel would have likely cost an employer roughly $800–$900.

But I work for myself. I just needed my client, The Hockey News, to approve my access so I could get to work.

The “Ask” and the Logistics

The NHL doesn’t openly invite media to the actual drawing, but as the saying goes: If you don’t ask, you don’t get. I asked, and soon I was joining three other local New York-area reporters for the event.

2026 NHL Draft Lottery at the NHL Network Studio in Secaucus, N.H.

Here is how I managed to pull off the entire trip for an effective cost of $250 CAD all-in.