How This Guy Got to Sit Courtside with Gary Vee

Editor’s note: The author of this article, Matt Calderone, is a Gary Vee superfan who submitted a tweet for the opportunity to sit courtside with him at a Knicks game. This is his story. 

The call came around 3 p.m. on a Friday.

I was skeptical at first. Was it a sales call? Was it a scam? Was I being punked?

After a few minutes, it became clear what was happening. The person on the other end of the phone, who introduced himself as “Max with Team Gary Vee,” told me that a tweet I had sent seven months prior and had long forgotten about was going to check an item off my bucket list.

Last July, well-known entrepreneur and social media influencer Gary Vaynerchuck appeared on a Barstool Sports podcast and spontaneously said he was going to take a fan to join him courtside for a Knicks game—and pay them handsomely on top of that. I happened to see the tweet sent out later by the podcast and immediately responded.

What I didn’t know at the time is that Max had been in touch with my colleagues behind the scenes and was plotting to get my reaction on video. Toward the end of the conversation, I felt all eyes on me in the office and knew something was up. Sorry, not sorry I was so calm, cool and collected during such a thrilling moment.

When I think of the Knicks, I think of my mom.

I grew up listening to her stories of watching the great teams of the early ’70s with her father: the strength and focus of Dave DeBusschere, the steely-eyed leadership of Willis Reed, the creativity of Clyde Frazier and the smarts of Bill Bradley.

Bonding with my mom over the Knicks instilled my love for the game and inspired me to play the sport at a young age. She had my uncle install a basketball hoop in our grass backyard when we moved into a new house when I was in middle school. She came to all my games and was my biggest cheerleader.

We experienced thrills and heartbreak together during the Knicks’ last extended stretch of high-quality play in the ’90s: John Starks’ dunk, Charles Smith’s series of missed lay-ups, Reggie Miller tearing our (and Spike Lee’s) hearts out, Jeff Van Gundy attacking Alonzo Mourning’s leg, and Allan Houston’s runner in the lane to clinch an intense first-round series against the Miami Heat.

Since then, it’s been nothing but despair as the Knicks have turned into one of the most poorly run franchises in the NBA. There have been countless low points, including the Isiah era, the forced trade for Carmelo Anthony that cut Donnie Walsh’s legs out from under him, Phil Jackson’s money grab and failed tenure, and fan-favorite Charles Oakley getting physically removed from his seats on a personal vendetta from the owner.

One of the few bright spots in the 2000s, Linsanity crescendoed in the days surrounding my mom’s death. His performances during that cold week in February offered a tiny distraction during a period of intense grief.

Kristaps Porzingis—the unicorn fans hoped would lead our path back to glory and the lone bright spot during Phil Jackson’s tenure—was traded the day before I got the call from Max. While the trade looks better with the benefit of time, it was a gut punch at the moment. Katie Baker perfectly captured the id of the long-suffering Knicks fan in the aftermath of the Porzingis trade.

For better or worse, Knicks fandom is in my blood. Despite the consistent losing and mismanagement, I am perennially hopeful that a turnaround is on the horizon.

My daughter Stella is two and a half, and I wonder if she’ll fall in love with the sport as I did. Being a Knicks fan today means something much different than it did when my mother watched with her father in the ’70s. I’m hopeful the tide will turn soon and Stella and I will have some competitive teams to appreciate together in the future. I’m also hopeful Clyde Frazier keeps broadcasting long enough for Stella to get to know him and his “stylin’ and profilin’” essence.

The day arrived. It took a lot of strength for me to leave my Free Oakley shirt in its drawer as I was getting ready that morning, but I didn’t want to give the owner a reason to have me escorted away from the court.

I picked up my ticket from the VaynerMedia office in Hudson Yards and walked a few blocks to the “World’s Most Famous Arena.” Gary would meet me there closer to tipoff, leaving me time to geek out over this VIP experience before meeting my host.

After getting my bearings, I saw Knicks president Steve Mills and nearly bump into Wally Szczerbiak on his way to do the pregame. I had a plate of Marcus Samuelsson glazed wings and miso-marinated sirloin and a Grey Goose and soda before walking along the court to my seat.

When I reached my seat next to the announcer’s table, I immediately saw the legend, and mom’s favorite Knick, Walt “Clyde” Frazier. Mom and I shared many smiles and laughs over Frazier’s gift of gab, a flair for the dramatic and superior sense of style. My sister, wife and I ate dinner at Clyde’s restaurant on mom’s birthday one of the years after she passed—I had my speech prepared on the off chance I’d bump into him that night. This time, all I could do was muster up a dumb grin and wave in his direction, but he was kind enough to smile and wave back.

After years of watching Knicks games and seeing the famous faces courtside on TV, it was surreal to be on celebrity row with Tracy Morgan, Michael K. Williams, Steve Schirripa and others.

Gary arrived right before tipoff. He was a gracious and generous host.

Working in tech and media, I’d been familiar with Gary Vaynerchuk since he penetrated the zeitgeist over a decade ago. I’d studied up on what he’s been up to recently after I found out that I was selected. It’s a lot! The conversation was easy, and he was interested in learning about me. We talked about our work and about being into sports and baseball cards growing up in suburban New Jersey. We both loved Latrell Sprewell, and I think I surprised him by telling him I used to rock a Golden State Warriors–era Sprewell jersey. He surprised me by telling me he used to go to the town-wide garage sale in my hometown of Butler. As expected from the Knicks of the 21st century, the quality of basketball was poor, but the experience was world-class.

Thanks, Gary, for a night I’ll never forget.

You can follow Matthew Calderone on Twitter here.