Breaking the Bank
Winston was driving the money transfer truck throughout the desert with Ted McAdams. Then Henry hid himself in the money bag and threw himself onto the road. Winston then spotted the bag and stopped the truck. When he and Ted came out from the truck, they thought that it was an official money bag and Winston put it into the truck without knowing that Henry was inside. He then drove the truck to the bank, where some security guards spotted Henry on camera and arrested him. Henry was sent to prison and Winston became a witness of the case.
Escaping the Prison
During the trial, Winston had to come as a witness because he was the only one who witnessed Henry's attempt to break into the bank. He told the judge everything that happened that day with all the details. However Henry hired Phoenix Wright for his lawyer. Wright then explained that it's impossible that Henry tied the knot from the inside of the bag and that Winston is the one who put Henry into the bag in an attempt to kidnap him, which was not true, but the judge believed him because he didn't know Henry had any special powers (as in the power to tie the knot in the bag from the inside). He responds with a worried, "You ca-youca-ica-no it ca-...THIS CAN'T BE HAPPENING TO MEEEEE!!!!!!" Then Winston was arrested for "kidnapping".
Infiltrating the Airship
One of the members of the Toppat Clan looks a lot like (or is) Winston, meaning he might have escaped prison and later became a Toppat Clan member. The Right Hand Man also resembles Winston, although because of their differing accents, this is most likely a coincidence.
Fleeing the Complex
When Ellie and Henry freed all the prisoners, he can be seen fighting a guard above them, meaning he got sent to The Wall some time before Henry.
- His name, age, and weight were revealed in the military scripts in Infiltrating the Airship.
- With Ted McAdams, he was the first policeman to appear in Henry Stickmin series.