I tried to follow instructions below and couldn't make it work. The in-game chat text still doesn't work. Please, teach me.
I have up-to-date TF2 and the fonts still show for me. The font issue was never solved by a launch option to the game, it was solved by a hack in our code. The hack needs to be enabled with a registry setting. Within the key [HKEY_CURRENT_USER\Software\Wine\AppDefaults\hl2.exe\Direct3D] the value named tf2_alpha_hack should have the string value "-game tf". You can enable the hack for other games that need it, like Portal and HL2:Ep2 by adding additional values separated by semi-colons. For example, set the value to "-game tf;-game portal;-game ep2".
Thanks,