Flipping Leaf Tickets for Additional Income; or not?

While on paternity leave, I saw an email come in stating "Leafs Playoff Presales starts tomorrow at 2pm". I thought, heck, I have never been able to get Leaf playoffs tickets myself. I am sure I can could flip these, worst case I will just go to a playoff game.

What Did I Buy and For How Much?

I was able to secure two sets of tickets. I was originally going to settle for one guaranteed set, then decided "hey, I can still get access to these tickets that would be great!". I was able to purchase tickets in the Gold section, on the corner where the Leafs shoot twice!

First Set

Sec 110, Row 23, Seat 3

Sec 110, Row 23, Seat 4

Second Set

Sec 117, Row 15, Seat 3

Sec 117, Row 15, Seat 4

With a cost of $3101 CAD, I now had 4 great tickets to Game's 4 and (potentially) 6 of the first round of the playoffs in Leaf's Nation! I was super excited and was expecting to make a few extra bucks flipping these tickets!

Posting the tickets!

Game 4 was posted for $1000 per ticket, Game 6 was posted for $1100 per ticket. The expected return after Ticketmaster fees was $3780, a smooth $679 for queuing up and finding some great seats to share with the public at a nominal finders fee. Or so, I thought...

Game 4

Two days prior to the game, the tickets sold. They flew up the shelf like hot cakes. The Leafs were down 2-1, this was going to be the game where they tied it at two! Highly desirable! SOLD!

I am sitting here, up $375.50 on the first pair of tickets. Nice!

Game 6

The return to Toronto, the Leafs down 3-1 in the series. The season on the verge of another heartbreak. Toronto fans are harsh and overly negative at these points. I wait and wait, the tickets are burning a hole in my metaphorical pocket. What do I do? Let's hedge my bets. At noon, game day, I drop my prices to breakeven, I take into account the margin I have made on the first set. I am baffled at the number of people dumping tickets below face value. I am not the only one looking at taking a loss on the tickets.

Three hours before game time. The tickets still aren't selling. Do, I want to go negative on these in order to dump them? Hell no. I reach out to some friends and family, "who wants to come to the game for $300 and beer", a completely fair offer if I say so my self. I felt like a number of people really did try to join, but, I unreasonably didn't give enough time to this grand opportunity. No takers, at that price, can I even get someone to come for free?

The Game

Luckily, I had a friend downtown, not a die hard hockey fan - actually - a person who had never been to a live hockey game, let alone a Boston - Toronto game, let alone a playoff game, let alone an elimination game, you get the point. He was very gracious and to his credit, I did not pay for a single thing while I was there.

My future career professional sports photographer, if I do say so myself.

The game ended in a 2-1 victory for the "good guys". They had successfully pushed for a Game 7 back in Boston. An event that had been a repeating nightmare for this group, but, this time will be different right?

The Result

The game was great. It did however cost me $1301, plus two uber rides and one train ride; approximately $1500. I understood the risk. I did get to see a great hockey game, it was a unique experience. I did get to save some money on the ticket expenses by selling the first set. I did "pick" the better of two games to go to.

However, the real winners here are the Boston Bruins who advance to the next round and Ticketmaster who generated at least $600 off of me. Which actually blows my mind. I think this was fun to try at least once, but, my advice is just wait until moments before the game and try and pick something up. Flipping long term probably does have a profitable path, it does come at a cost.