Allen is a 70-year-old realtor based in Tsawwassen, just outside Vancouver. He’s spent decades in real estate, and over that time, watches have quietly been part of his life and identity.

“I bought my first Rolex… 45 years ago.”

That first piece was an Oyster Perpetual. Not long after, he added more to his collection, including a Day-Date he later let go.

“And I wish I wouldn’t have sold it now.”

Over the years, his collection evolved. Some watches stayed, some moved on, and a couple even found their way to his wife.

“My wife took both of those… I haven’t been allowed to wear them for over 20 years.”

His interest never faded.

When Allen first came across Wolf Watch Club, it wasn’t random. It came through a trusted recommendation during a conversation with a local jeweler he had done business with for years.

“He said… the one I know is legitimate is Wolf Watch Club.”

That mattered.

“There’s so many scams on the internet right now… I’m very, very cautious.”

Allen had seen it all online. Ads, pop-ups, offers that didn’t feel right.

“Lots of times, my advanced security will block them.”

But this one was different.

So he gave it a shot. Nothing excessive. Just a few entries across a handful of draws.

“I haven’t been in many… I’ve been in the last four or five or six maybe.”

And then, out of nowhere, it happened.

Allen won the Rolex GMT-Master II “Bruce Wayne.”

He didn’t even see it live.

“They saw it and they phoned me.”

At first, he didn’t believe it.

“I thought… I think you’re looking at something else.”

Even his family was cautious.

“My son even emailed you back.”

In today’s world, that hesitation makes sense. Allen had recently experienced a scam himself, which only reinforced how careful he had become online.

“I’m very, very, very, very cautious.”

But this time, it was real.

When the watch arrived, the moment hit immediately.

“I love it. It’s beautiful. I’m thrilled.”

Holding it in his hands, seeing it up close, it all clicked.

“It’s an absolutely beautiful watch. I’m very thrilled. I appreciate it.”

There was just one small problem.

“I can’t get it over my hand.”

Even that didn’t take away from the moment. Standing there, holding it in the box, knowing it was his before even putting it on.

And for Allen, this wasn’t just a random win.

“Oh yeah… this is on my wish list.”

It meant something.

His family felt it too.

“My kids are thrilled for me… because of course they’ll get it in the end.”

A full-circle moment. From buying his first Rolex decades ago, to now winning one he truly wanted.

What stood out just as much as the watch was the experience itself.

“You are so well run. And so transparent… it’s wonderful.”

That trust, especially for someone as cautious as Allen, made the moment even stronger.

From a trusted recommendation, to a few entries, to holding one of the most sought-after Rolex models in the world, Allen’s story came together quickly.

And he’s already looking ahead.

“I’ll be one of your best customers from now on.”

Enrique has lived his whole life in Miami, dedicating his career to teaching middle and high school students. This year marks his final chapter in the classroom before retirement.

And somehow… everything came together at once.

His birthday landed on April 6th.
And just days later, he won the Omega Speedmaster Moonwatch (White Dial).

“Oh man… everything coming together this month. My birthday, the Speedy… it’s literally the Moonwatch.”

For Enrique, this watch is more than just a piece. It goes all the way back to childhood.

“I remember being 8 or 9 years old, watching the moon landing on a black and white TV… this is a full circle moment.”

He’s been part of the Wolf Pack since the beginning.
43 draws. Almost never missing a live.

And the one time he did?

He was working late on lesson plans for his students.

Later that night, he watched the replay… and heard his name.

“I was shocked. I called my daughter and asked if this was real… we were all in shock.”

Enrique has loved watches his entire life. His passion deepened about a decade ago when a friend introduced him to Grand Seiko.

But the Speedmaster always stood apart.

“It’s not about the cost… it’s the story behind it. The Moonwatch.”

From a Swiss Army watch… to Grand Seiko… to dreaming of a Rolex Explorer… and now, the Speedmaster.

“The Speedy is going to be a magical story to tell… an unattainable goal that came true.”

Despite 43 draws, he never stopped showing up. Sometimes with one ticket, sometimes more.

“I’ve never won anything big… maybe $50 once. This is unbelievable.”

Now, he’s counting down the days until it’s on his wrist.

“That’s when the real excitement will start again.”

And maybe the best part?

“My students are going to be excited to hear about this… they’ll probably go home and tell their parents.”

When asked about his experience:

“My experience with WWC, Jory, and Jessie has been great.”

And his dream future draw?

A 100th anniversary Rolex.

For now, though, this moment says it all:

“It’s like walking through a blizzard… and not a single drop touches you.”

Caleb Ribeiro is first and foremost a family man.

A stay at home dad to two young daughters, Caleb has chosen to dedicate his time to raising his girls and being present for every stage of their lives. It is a role he genuinely enjoys, getting to watch them grow up and being there for the moments that matter most.

He got into watches about two years ago and has been enjoying the journey ever since. He spends time watching creators like Jory Goodman on The Time Teller and Teddy Baldassarre, picking up knowledge along the way and simply enjoying the content.

When asked what drew him into watches, his answer was simple.

“For men, this is one of the few pieces of jewelry to wear.”

But for Caleb, it means more than just that.

“I can leave it for my daughters, and they can enjoy it for years to come.”

His journey started with a black Seiko Essentials watch, his first real piece. From there, he moved into more significant watches, including a Grand Seiko GMT with a black dial and red GMT hand, a piece he really appreciates for its precision and design.

Living in an area with limited access to authorized dealers, Caleb has been thoughtful about how he builds his collection. He picked up a Tudor Black Bay 58 from a local dealer, and later, to celebrate their 20th wedding anniversary, he and his wife chose two Omega watches together, an Omega Seamaster 75th Anniversary Summer Blue for himself and a Seamaster Aqua Terra Shades for her.

Caleb discovered Wolf Watch Club through The Time Teller. Both him and his wife decided to give it a try together.

Why not.

Since then, they have entered a number of draws as a couple.

For Caleb, watches are not just about owning something nice. They are about meaning, memories, and having something that can be passed down one day.

Looking ahead, he would love to see the new matte medium blue Rolex Oyster Perpetual featured on Wolf Watch Club.

For now, he continues to enjoy the journey, both as a watch enthusiast and as a dad building something meaningful for the future.

Kristopher and Jennifer Chadwick, longtime members of the Wolf Pack, live in a small farming community in Alberta with a population of roughly 800 people. Since September, the couple has been entering draws together, turning watch collecting into a hobby they genuinely share and enjoy.

Kristopher works as a foreman in construction, operating in areas with cranes and other heavy duty machinery. Earlier in his career, he worked in a chemical environment where any battery powered device was strictly prohibited due to explosion risk. Because of this, mechanical watches were not just preferred, they were essential. His first practical choice was a durable Seiko 5 watch suited for demanding work conditions. Over time, that necessity grew into a genuine appreciation for the craftsmanship and engineering behind mechanical timepieces.

Naturally mechanically inclined, Kristopher enjoys working with machines, mechanical sports, and vehicles, and built the motor in his own diesel truck. As his interest in watches developed, he added pieces from brands such as Christopher Ward and Tudor to his collection. One watch, however, remained on his list with an authorized dealer in Edmonton, the Rolex Submariner Date.

Jennifer has been supportive of the hobby from the beginning and participates alongside him. She was especially excited during a previous Piaget draw, where she finished as a runner up. For the Chadwicks, Wolf Watch Club became something they experienced together each week.

They first discovered Wolf Watch Club through Jory Goodman’s YouTube channel, The Time Teller. Intrigued by the concept and reassured by the transparency, they decided to give it a try and continued entering draws over the following months.

Their win came during the Grail draw for the Rolex Submariner Date Ref. 126610LN. At the time of the draw, Kristopher held 8 tickets out of 2,600 total tickets.

On draw night, Kristopher and Jennifer were getting ready to leave the house, as Jennifer works some distance away from home, but they tuned into the live stream together before heading out. Their dog was with them, and they listened to the draw as it happened.

When Kristopher’s name was called, the reaction was immediate disbelief. Jennifer recalls the moment clearly
“Kristopher Chadwick?? …crazy…”

What started as shock quickly turned into excitement as they realized the win was real.

The Submariner Date was a watch Kristopher had been waiting to obtain through an authorized dealer, with an estimated wait of about three years. Having recently purchased a blue Tudor Pelagos 43, he had not planned on acquiring another large watch anytime soon, which made the win an even bigger surprise.

After entering more than 33 draws since joining in September, the Chadwicks’ persistence paid off with one of the most iconic sport watches in the world.

For Kristopher and Jennifer, the win represents more than just a timepiece. It marks a shared experience, a memorable moment together, and the culmination of months of participation as part of the Wolf Pack.

Their story is a reminder that sometimes the name you hear called next could be your own.