Why code enters if when the condition is not met?

It's best to look at this picture first before reading.
The image and title is pretty much self-explanatory, but I'll still ask: why does this code enter an if statement when it's clearly not supposed to? I checked for typos and I didn't find any.
I'm using VS2015 and the project is based on .NET Framework 3.5

Edit

What might be worth adding: when the debugger stops on the first if statement seen in the image above, the preview of what value holds is not available.