http://bugs.winehq.org/show_bug.cgi?id=12327
--- Comment #10 from Gary Pendergast winehq@pento.net 2008-05-03 09:52:42 --- (In reply to comment #9)
Could you try if setting the hl2.exe to win98 helps?
Changing hl2.exe to win98 makes no difference. Changing Steam.exe to win98 causes it to fail to launch with a message to "Please turn off 'compatibility mode'".
I tried launching the game both from within Steam, and from the command line, in the team fortress 2 directory: shell> wine hl2.exe -game tf