A workaround is to use the ClientTemplate and change the strings manually with some JavaScript (http://www.telerik.com/help/aspnet-ajax/htmlchart-client-templates-for-tooltips-and-labels-execute-javascript-and-display-html.html), e.g.:
<telerik:RadHtmlChart runat="server" ID="RadHtmlChart1" Width="400px" Height="400px">
<PlotArea>
<Series>
<telerik:BarSeries>
<LabelsAppearance>
<ClientTemplate>
#if (value > 0) {# $#=value# #} else {# -$#=value * -1# #} #
</ClientTemplate>
</LabelsAppearance>
<SeriesItems>
<telerik:CategorySeriesItem Y="20" />
<telerik:CategorySeriesItem Y="10" />
<telerik:CategorySeriesItem Y="-30" />
</SeriesItems>
</telerik:BarSeries>
</Series>
</PlotArea>
</telerik:RadHtmlChart>