For some reason the problem was that I was using a button in the datatemplate as
<Button Content="Edit" Style="{StaticResource HyperLinkButtonStyle}" Click="EditButton_Click" />
Something about the Button was making the gridview have to first focus itself into the view before a subsequent click on that button would fire the click event in the cases where it was not fully fitting on the screen..
I ended up doing the workaround of simply using a telerik label and giving it a MouseLeftButtonDown event
<telerik:Label Content="Edit" TouchDown="EditButton_Click" MouseLeftButtonDown="EditButton_Click" Style="{StaticResource HyperLinkStyle}"/>
Pretty sure you should be able to use a regular label as well
The HyperLinkStyle is just a style that makes the label underlined and gives it a color and hover state
<UserControl.Resources>
<Style x:Key='HyperLinkStyle' TargetType='telerik:Label'>
<Setter Property='Template'>
<Setter.Value>
<ControlTemplate TargetType='telerik:Label'>
<TextBlock TextDecorations='Underline'>
<ContentPresenter TextBlock.FontFamily='Segoe UI' TextBlock.FontSize='13'/>
</TextBlock>
</ControlTemplate>
</Setter.Value>
</Setter>
<Setter Property='Foreground' Value='#195AE0' />
<Style.Triggers>
<Trigger Property='IsMouseOver' Value='true'>
<Setter Property='Foreground' Value='Red' />
<Setter Property='Cursor' Value='Hand' />
</Trigger>
</Style.Triggers>
</Style>
</UserControl.Resources>