Wolf Watch Club Winners
Competition Winner #62
Jim is originally from Oklahoma.
“Originally from Oklahoma… I was born and raised out there… went to school and college all in Oklahoma.”
He later built his career in Texas, starting out in aerospace before spending about 20 years in oil and gas.
“I’ve always been a big fan of space travel, jet engines… that’s where it all started… and then I found myself in oil and gas… for about 20 years.”
Three years ago, he made a shift.
“I left the big company life to go start up my own software company… we’re in the third year of our startup.”
Now based in Houston, he’s in a new phase of life, building something of his own, while also planning what’s next personally.
“I do have a serious girlfriend… we’re on the road to marriage.”
Outside of work, Jim keeps busy. He travels often, usually a few international trips a year, and spends time around photography, art, and experiences like Burning Man.
“I do about maybe three international trips a year… I’m an avid photographer.”
But one thing that’s been consistent through it all is watches.
“I’ve had a strong love for watches my entire life.” It started early. “I got my first ever watch when I was like nine years old… my aunt from Germany gave me a watch… and I wore that like I was wearing a medal.”
Over time, that turned into collecting.
“It wasn’t until halfway through my career that I started actually purchasing a few pieces… I’ve got a pretty decent collection.”
Still, there were gaps. One of them was Omega.
“This is my first Omega… this is a huge one for me.”
The Speedmaster had been on his mind for a while.
“I’ve been wanting one for a long time… it’s got history, it’s a chronograph… it’s a classic piece.”
In fact, he had already gone to the boutique.
“I had gone to the Omega boutique here in Houston… I was like, I really need to get a Speedmaster.”
Then the draw came up.
“I thought… okay, this is just a sign I have to do this.”
So instead of buying it, he entered.
“I was about to buy one anyway… so I think I went pretty heavy on this one.”
When the live draw was taking place, he almost missed it.
“I was actually not even in the room… I just heard my name being said from down the hall.”
The reaction was immediate.
“I was so surprised… so caught off guard.”
The watch arrived quickly, and by the time Jessie called him, he was already wearing it, leaving the boutique after getting it sized.
“I’m literally leaving from the Omega boutique right now… I went over there to get a couple of links taken out.”
For Jim, it wasn’t just about the watch itself. It was also the experience around it, and the people.
His brother-in-law Matt had already won before, and now the momentum is spreading.
“My friend circle is actually going so hard right now… my buddy Mike just made a purchase… my buddy Bobby made a purchase…”
At first, they didn’t even believe it.
“They initially thought that I had won something like a used watch… and when I explained… it’s brand spanking new… they were just in absolute disbelief.”
Even his family is starting to come around.
“My brother… loves watches… he’s been trying to dip his toe in… I think we finally broke him over… I think he’s gonna jump in on one of these now.”
And for Jim, that’s part of what stands out.
“It’s a small community… it’s a really fun community… it just feels… warm.”
Especially compared to others he’s seen.
“It just doesn’t feel the same… these other watch clubs feel super gimmicky… you guys truly humanize it.”
In the end, the watch itself was something he had already chosen.
“And I was like… of all the watches right now… an Omega would be perfect.”
This time, he didn’t have to go back and buy it.
He just had to hear his name.
Jim Nellikunnel won the Omega Speedmaster Hesalite on April 26, 2026
Competition Winner #61
Andrew Bennett had just been talking about the “Root Beer” earlier that week. Then he opened his email.
He’s a physician by trade, someone who’s built his career on precision, patience, and long hours. Watches, for him, started as something personal. A milestone tied to hard work and progress.
“My first serious watch was an Omega Speedmaster… I rewarded myself with when I finished training.”
That watch stayed with him for years. And when it finally gave out, it pushed him deeper into the world of watches.
“The estimate was greater than the value of the watch… so that got me into looking at other watches.”
From there, his collection grew. A Rolex Datejust. Then an Explorer.
“At this point I really got the bug for watches.”
Andrew discovered Wolf Watch Club through a YouTube creator he followed.
“You guys sponsored him… and that’s how I found out about Wolf Watch Club.”
He didn’t jump in heavily. He played selectively.
“I may have done seven or eight raffles.”
Then came a moment that felt almost too perfectly timed.
While in Toronto for a conference, Andrew was talking watches with a colleague.
“He brought up the root beer… I thought, ‘Oh yeah, that’s a beautiful watch.’”
Later that same week, he saw it listed.
“I thought, ‘Wow, that’s pretty neat.’ So I bought 10 tickets.”
What happened next didn’t feel real.
“I opened my email to see that I won… which is pretty bananas.”
After a long flight back home, he landed, checked his phone, and saw it.
“When I land, I see that I won.”
His reaction was immediate.
“My first thought was that this is proof that we really do live in a simulation… like Donnie Darko style or something.”
“That was startling. No lie.”
He kept it close at first.
“I haven’t really told anyone… other than a couple of close friends and family.”
What made the win even more meaningful was how aligned it felt.
“I have been more interested in world timers and GMTs.”
“I was pretty excited to get a different version of a GMT… especially since it’s so difficult to get usually.”
Outside of watches, Andrew balances his profession with creativity.
“I’ve been spending my free time learning stone carving and clay modeling of figures and portraits.”
And when it comes to the experience as a whole, one thing stood out.
“It’s wonderful… otherwise a lot of these watches wouldn’t be accessible to people.”
He summed it up best.
“It feels like a private club… a secret entrance into watch collecting.”
From a conversation at a conference, to 10 tickets, to winning the very watch he had just been talking about, Andrew’s story came together fast.
And just like that, the Root Beer was his.
Andrew Bennett won the Rolex GMT-Master II Root Beer on April 19, 2026
Competition Winner #58
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.”
Allen Schwabe won the Rolex GMT-Master II Bruce Wayne on April 12, 2026
Competition Winner #60
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.”
Enrique Senger won the Omega Speedmaster Moonwatch (White Dial) on April 12, 2026
Competition Winner #56
Miguel Baptista, 23, lives in the Netherlands just outside Amsterdam. He works as an AI coach, helping businesses and influencers integrate AI into their online shops. Outside of work, life has been busy in the best way, especially with a new puppy at home.
Miguel has always liked watches, but never considered himself a serious collector. He knew that if he were to buy a “first big watch,” it would be a Rolex, something to work toward over time.
After discovering Wolf Watch Club, he decided to give it a try.
He entered a few draws, some with better odds than others, and made a habit of tuning into the live draws each time, listening closely to hear if his name would be called. By the time of this draw, he had entered four in total.
The one he ended up winning was the one he expected the least.
“This is the one I least expected to win in… because the ticket count was higher.”
On draw night, Miguel was in bed while his girlfriend was asleep beside him. Like the previous draws, he had the live stream on, listening in.
Then he heard it.
His name.
At first, it did not feel real. He was in shock, trying to process what had just happened. The moment truly sank in when he got to speak with Jory live during the stream.
“Absolutely crazy… I couldn’t sleep for two hours after that.”
Still wide awake from the excitement, Miguel went downstairs to tell his stepfather and his mom, who were still up at the time. They shared the moment with him as the reality of the win began to settle in.
Over the next couple of days, he found himself talking about it constantly, sharing the story with friends and even clients he works with.
“I’ve been talking about this for the last two days.”
At first, like many people, Miguel had some skepticism. What helped build trust for him were the winner stories, the reviews on Trustpilot, and seeing other players from the Netherlands.
“A lot of people think this might be a scam, but getting on the call made it feel real.”
Winning a Rolex GMT Master II made the experience even more meaningful, especially knowing how difficult these watches can be to get.
“It’s awesome that you guys can get these watches… I know it’s a hard one to get.”
For Miguel, this was something he never expected to happen.
“This was a once in a lifetime opportunity to win a watch like this. I’m super appreciative.”
And even after the win, he is not done.
Miguel is already entered into the next Grail draw for the Rolex GMT Master II “Bruce Wayne.”
His message to other players is simple
“You never know… I also didn’t think I could win.”
Miguel Baptista won the Rolex GMT-Master II Batman on March 29, 2026
Competition Winner #57
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.
Caleb Ribeiro won the Longines Moonphase on March 29, 2026
Competition Winner #55
Arnoldo Saucedo won the Winner’s Choice Black Bay Chrono on March 22, 2026
Competition Winner #52
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.
Kristopher Chadwick won the Rolex Submariner Date on March 15, 2026
Competition Winner #54
Genki McClure won the Santos de Cartier Medium on March 15, 2026
Competition Winner #53
Bryan Gibson won the Omega Speedmaster Hesalite on March 8, 2026
Competition Winner #50
BRIAN HUGHES won the Rolex GMT-Master II “Root Beer” on March 1, 2026
Competition Winner #49
Richard Hendifar won the Omega Seamaster Diver 300M on February 22, 2026
Competition Winner #47
Rajamurugan Meenakshisundaram won the Rolex GMT-Master II “Bruce Wayne” on February 15, 2026
Competition Winner #48
Philip Hislop won the Valentine’s Choice: Tank Must or Française on February 15, 2026
Competition Winner #46
Domenic Dehoyos won the Omega Speedmaster Hesalite on February 8, 2026