Smiley doesn't appear to be the most well adjusted person in the world. His mannerisms and attitude make his sanity highly questionable. His appearance has made more than one social situation uncomfortable. He stands 6'1" and weighs 195 lbs. His hair, though originally brown, has been dyed blonde and cropped short. His eyes are blue in color. Most of the time he wears a old pair of sunglasses. Smiley can look even more demonic than he acts if he takes the time. He has been known to paint his face a dull yellow and draw the outline of a sinister "Smiley Face" on his features. When combined with the number of razors sprouting out of his hands, the effect is more than sufficient to be unsettling.
Smiley's clothes are not in terrible taste. He does wear suites occasionally and a nice coat. Though Smiley is not eccentric all of the time, it apparent that he does have a different set of moral values than the average person. He is moody, but doesn't manage to exert some amount of self control over himself.

No matter the day, Smiley always makes sure to have one or two buttons on his person. These clip-on buttons vary greatly with different slogans. Some examples are: "Have a Nice Day" "Elvis Lives" Smiley Face w/Sinister Smirk "Don't Run We Are Your Friends" Button with Nuyen Symbol "Meat is Bad"

Smiley is not the worlds most understandable person and he makes a poor role model by anyone's standards. He can be overly violent and disillusioned. At the same time he demonstrates a calm control when he's thrust into a potentially dangerous situations. The truth is that his mind doesn't register the danger to himself. He also doesn't realize the pain that he causes to others because he doesn't feel any connection to him. A classical case of separation stemming from his lonely childhood.

His BTL habit hasn't helped matters any. Constantly slotting chips have put him on the border line of sanity. Smiley is not an unthinking animal and is capable of sharing his insights and his opinions. The problem is that his ideas are on a completely different level.
Smiley's childhood wasn't the best one could hope for. His mother died at a young age and he was raised by his father. His father was the owner of a small copying business and he was obsessed with his work. He didn't spend much time with his son. Instead Smiley spent most of his time with the electronic babysitter known as a TV. In school he got into more trouble than he was worth. Several times he was threatened with expulsion.

He joined the military at the age of eighteen. By the time he was twenty-two he had been transferred to a special unit called "Harry's Bunch." They dealt primarily in small operations were they would complete specialized operations as quietly as possible. Most of their activities were denied by the UCAS government. Smiley received most of his cyberware during this time. Most of the implants were done by a surgeon named Dr. Thaddeus Simms.
When Smiley was twenty-five, his tour of duty was up and he received an honorable discharge. He had no idea what he was going to do now. He filled his first few weeks off by accepting bouncer jobs and working in small clubs. He was later fired because of his treatment of customers.

Eventually a man named "Mr. Bishop" approached him. He explained that he heard of Smiley's exploits in the military and that he had ties with Smiley's old unit. Mr. Bishop recruited Smiley into an organization that was referred to as "The Company." Essentially The Company is an international organization who's controllers would gather a flock of the worst men in the world. Assassins, murderers, serial killers, and terrorists just to name a few. This people were gathered together, then hired out by the Company to perform deniable operations for whoever could pay.

Smiley worked with the company up until the beginning of 2059. A few months before he was kicked out Smiley went on a job. He was to enter a small Chinese restaurant and kill the owners while they had a meeting with members of the Yakuza Swordfish Clan. He did his job and hurt a lot of people like he was told. Unfortunately one of the people he "hurt" was the niece of one of the Company's primarily controllers. The niece was no more than ten. Smiley had shot her in the gunplay. Months later Smiley was given a card, asking him to fly to San Francisco in the California Free State.

In San Francisco he was to go to the Winterwood Maximum Security Prison which was due for its grand opening in two days. When Smiley arrived he found himself to be with several other Company employees. Each of the other people with him had a small black business card that was given to them by Mr. Bishop. The card told the holders name and what he or she had done to dishonor the Company. Smiley's held the picture of a small girl whom he had shot with the word "Lost Innocence" wrote above it.

After he was released Smiley took his half of the money and told Vault and Julia goodbye (actually his words sounded more like Piss off!). He took the next flight out of San Francisco. Since he left he has spent most of the money and still hears from Mr. Bishop on rare occasions. Though the business partnership the two had is strained to the point that Smiley would rather hit him than chat with him.