Winston, the Raiders' director of player engagement, wanted to know which off-the-field program Cowser wanted to participate in during the offseason.
"You've got to better yourself out of football," Winston told Cowser, who had a sack and a fumble recovery in six games last season.
Presented a list of activities, Cowser turned his nose up at each, until being asked what "unique" talent he might have.
"I speak Chinese," said Cowser, who picked up the language while serving a two-year LDS mission in Hong Kong and Macau from December 2009 through December 2011.
Winston went to work and Cowser landed an internship with NFL China, which is headquartered in Shanghai. Those two weeks in China and an ensuing Internet presence landed Cowser an unlikely role as the face of the NFL for that country and its 1.4 billion potential new fans.
Cowser has since done a handful of Internet videos for the Chinese audience explaining the decidedly American game to an eager audience from the most populous country on the globe.
He has described the NFL scouting combine, taken his Chinese audience behind the scenes of the NFL draft fan experience, broken down picks 2 through 5 in the draft and facilitated an interview at the draft in Philadelphia with ESPN's Louis Riddick.
The draft pieces garnered more than 1.1 million views each.
Now, through ESPN International partner Tencent, Cowser is going deeper. The second-year NFL player, who was an undrafted free agent out of Southern Utah, is the host and star of his own webisode series that will air in China every Wednesday -- Oct. 4 though Jan. 21.
"I love it," Cowser said this week. "It's awesome. A lot of us take pride in taking part in something bigger than ourselves, right? I mean, that's why we love football. You're surrounded by brothers. You're surrounded by things that are bigger than yourself. To be able to speak Chinese allows me to be a part of something even greater."
With the blessing of the Raiders, a camera will follow Cowser around during the week to show his Chinese audience how life in the NFL works, while expanding the NFL's brand in the Asian market.
The entire show will be in Chinese -- with English subtitles domestically -- and Cowser will discuss the team's protest and show of unity during the national anthem prior to last week's loss at Washington in next week's premier webisode.
Cowser, who visited late martial arts star Bruce Lee's Hong Kong home, is already using his "Chinese Connection" to interact with and cultivate his Far East fans via his Chinese Twitter account.
"Basic stuff," Cowser said. "What's this person like? What's that person like? Good luck in the game."
The project's senior editor, Michelle Zhang, said Cowser was recently asked his goal in a game.
Cowser's answer? To one day score a touchdown and jump into the Black Hole. Surely that required further explanation for his overseas audience.
"I have an opportunity to show the Chinese people a sport that I love, people that I love, and just bridge a gap between cultures," Cowser said.
"It's China. What other team has this opportunity? What other player in the NFL speaks Chinese?"
As such, he can introduce new fans to one of the Raiders' best-known slogans: "Just win, baby."
Cowser huddled with Zhang, to make sure he was on point and had the accents just right as she wrote out the characters and Cowser exhaled.
"Jiu yao ying," he said.