Well-trained. Bigboy buddy Milton holds his friend’s latest merch: a shirt with an image of them as The Simpsons characters.
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Meet Anti Shoe Expert: Bigboy Cheng’s BFF, second-in-command, and Garth to his Wayne

If you’re a fan of sneaker collector Bigboy Cheng’s comedy and unboxing videos, you’ve come across the constant butt of his jokes: @antishoeexpert, or Milton Sy in real life.
Bam Abellon | Jun 19 2019

Milton Kaw Sy is known in the world of social media as the Anti Shoe Expert, and a few months ago, he was definitely that, a “non-expert,” on shoes.

But that was a few months ago.

Today, he is still not a specialist but his footwear knowledge has improved by a lot. What he’s really become, however, is that new kid in school whom everybody wants to be friends with. Thanks in huge part to the hilarious antics he and best friend Bigboy Cheng —the art impresario and longtime shoe expert — frequently unleash on YouTube, IG and Facebook.


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Now people want to sit at his table—and ask him where he got his kicks.

Milton, who turned 43 last January, was a toy collector first before he was introduced to the world of sneakers. When he was a kid, he had a fairly big collection of toys—mostly robots—a large part of which he has kept in the San Juan condominium unit he currently shares with his wife, Liza, and their three sons.  

He stopped collecting them around 20 years ago, when he had to focus on the family’s factory, and when his kids learned how to open the boxes and play with his precious collectibles. A few years ago, however, he picked up where he left off, and his toys might increase in number faster now given his current “status” in the collector’s world.  While the tales behind his toy collections go as far back as his childhood days, the story of his shoe collection started only in high school, around the time he met Bigboy, at the Grace Christian High School in Quezon City.

Many of Milton's toy collections are robots, like the red Optimus Prime above. He says this line was originally launched in the '80s, and was re-issued sometime in 2000.

Although they were born the same year, Milton belonged to a higher batch in school. Still, they knew of each other early on, and would often meet after classes. It wasn’t long before they became good friends, especially because almost immediately, they found out they had the same sense of humor. “There are things that are funny to you, but when you tell people about it, they don’t laugh,” Milton says. “Pag kami, tawa lang kami nang tawa. Same kami ng frequency.They also love listening to music and, even in those younger years, already had their own various collections.  

The two somehow parted ways when Milton left for the US to work. Bigboy traveled around the world and then studied for a few years in Japan.

This is the OFF-WHITE x Nike Zoom Fly SP. It's a collaboration piece from Nike and American designer Virgil Abloh.

They rekindled their connection a few years later, when they were both back in ‘Pinas. Milton and Bigboy found themselves bonding again: first, through badminton sessions at a club Milton co-owned. Then the badminton games turned into basketball games, and the two have not been separated since. Today, they play basketball almost every day at Bigboy’s San Juan house. Yes, these two quipsters are neighbors as well. You can just imagine the endless dirty jokes and off-cam shenanigans.

Buddies since high school: Cheng and Sy.

Milton says Bigboy has always been into streetwear, having had his own Supreme collection at a time when very few people in the Philippines knew that the skater lifestyle brand existed. For his part, Milton was more into the business casual look: Cole Haan, Lacoste, Ralph Lauren. “Pag suot ko ’yong Cole Haan, ’yong mga tao, ‘Wow,’” Milton recalls. “I grew up thinking na pag naka-leather-shoes, maporma.” He even wore his Cole Haan pair once while playing basketball, and when he explored the Crystal Cave in Baguio City. “Dumulas ako, muntik akong mamatay,” he says, laughing at the recollection.

Eventually, Bigboy’s fashion aesthetic rubbed off on him. “Natuto na din akong mag-hoodie-hoodie,” Milton says.

Milton's growing shoe collection find their place in the corner of his San Juan condominium. In this picture, the Anti Shoe Expert is wearing a pair from Balenciaga.

Bigboy’s Instagram account had its first post in January 2014. On his feed are photos of shoes (lots of shoes), his family, his colleagues, and his friends, including Milton. His account has more than 73,000 followers. In April of 2018, Bigboy decided to launch his own Youtube channel, Big Boy Cheng. The videos are mostly sneak peaks of his collections, his product reviews, and his unboxing materials.

In his first few videos, Milton was a “recurring character.”

Then, in one video where Bigboy was going to unbox a pair of shoes, the Secret Fresh owner left an unboxed pair of sneakers on the table. “Makalat sa mesa no’n,” Milton recalls. “So tina-try kong ibalik ang mga sapatos.” Milton had a hard time putting back the shoes in their own box—a challenge caught on camera. The footage made it to the final video, and the comments section was hilarious. “‘Ano ba ’yang kasama mo, hindi marunong magbalik ng shoes?’ Sa loob-loob ko,” says Milton, ‘E, sa buong buhay ko di naman ako nagbabalik, e. Pag nilabas ko, isusuot ko na.’”

Milton says this is a special pair as this was given to him by his best friend Bigboy Cheng. It's one of the pieces in Nike's "What The" Dunk collection.

And thus he was baptized—by Bigboy, of course—the Anti Shoe Expert.

In September 2018, Milton created his Instagram account with that name (@antishoeexpert). Now he has around 17,500 followers. That month, he also began taking shoe collecting a little more seriously. Around that time, someone sent Bigboy a pair of then-unreleased Yeezy Boost 350 V2 Static, in size 9. Bigboy is a size 11. He gave the pair to Milton. Think of it as a welcome gift from the sneaker collector gods.

Before becoming the Anti Shoe Expert, Milton was already a fan of the Yeezys and the 4Ds from Adidas.

“Ang ganda pala,” he thought to himself when he wore the pair. He only had three pairs of sneakers then. In less than six months, he was able to grow his collection to more than six times its size. He also become Bigboy’s second in command: he who entertains guests and customers when Bigboy’s schedule becomes too crowded. In fact, he reiterates, when he started his Instagram account, it was to promote the ventures of his friend.

The hoodie that bears their image.

Now, Milton and Bigboy are in talks about making their own toys. They also just launched a shirt and hoodie collection with their faces (patterned after the characters from The Simpsons) printed on them. Milton may not be a shoe expert just yet, but he gets his hands on some of the most coveted pairs in the world. He might have to remove the first four letters from his Instagram handle soon.


Photographs by Pat Mateo