“I am optimistic from head to toe. I’m a very optimistic person. I will always be an optimist,” Webster said.

Webster has some experience prevailing in situations where he has no knowledge. When he was tapped to coach the West Orange High School volleyball team, he knew absolutely zip about volleyball. But he knew a thing or two about coaching, so he signed on after learning the team had cycled through seven coaches in three years. He focused on strengthening the players’ relationships and by the season’s end, he’d coached them to the team’s first ever Metro Championship.  

He’s already planning ahead to build relationships with voters by meeting small groups of District 11 residents at house parties. 

“I’ve already set up a few and continue to meet in groups of 10 and 15 all over,” Webster said.

Opposition and frustration 

It was frustration with Congressman Webster’s inaccessibility to constituents and overall opposition to the Trump administration that propelled Webster into the Congressional race.  

Webster — who calls himself “the good Webster” —  routinely posts videos about the current administration and Congressman Webster on the Instagram page he set up for his campaign, complete with a donation link. The first event he attended after filing his candidate paperwork was Clermont’s No Kings rally where he described the crowd as “frustrated” and “fed up,” and said he was “ready to get started in this race.” 

“One of the most necessary abilities is availability,” Webster said. “Congressman Webster is not available. He does not hold town meetings … He doesn’t lead and he doesn’t understand, in my opinion, what his constituents need. He doesn’t relate anymore; he is a career politician.”

The irony that now he has become a politician too is not lost on him. 

“As soon as you file for office, you’re a politician,” Webster said. “When I joined the Army, I couldn’t go up to the drill sergeant and say, I’m not a soldier. No, you’re a soldier, day one. You’re a politician day one, and day one you have to be a leader.”

An analyst’s perspective 

Webster grew up in Miami, began coaching youth sports at 13 and joined the U.S. Army right out of high school, serving for “double digits” as an electronic warfare signals analyst, intercepting and interpreting messages from foreign adversaries. It was in the Army where he learned to size up various situations. 

“You can say all you want when you go, This is what I’m going to do and this is what I’m going to do,” Webster said. “Realistically, when I get to D.C., the first thing I have to do is evaluate the situation … Then you open lines of communication and find areas you can improve by communicating. Then you can form an action plan.”

Webster supports legislation to stop phone scams, which he said have become a significant issue in District 11 where robo calls have targeted elderly citizens who he said may be more likely to be taken in by callers claiming to be from trusted institutions, like banks. 

He also champions veteran’s issues, such as the Major Richard Star Act. If passed, it would allow medically retired veterans to receive both disability compensation and medical retirement payments.

“There’s one senator holding it up in committee, Sen.[Roger] Wicker (R-MS) [the Republican chair of the Armed Services Committee]. One of the first things I would do, even though I’d be a congressman, is try to talk him into passing that bill,” Webster said. 

“Passing a bill that you start as a junior congressman is not easy, but finding bills that are already out there is the logical way to make your first footprint,” Webster said. “My goal in Congress would be to support legislation that serves veterans and working families.”