I was able to successfully install Contract J.A.C.K. in a WinXP bottle on the following machine:
Soyo SY-7ISA+ Intel i815 Motherboard
Intel Pentium III 866 MHz Processor
512 MB SDRAM
PNY Verto GeForce FX 5200 AGP 8x 256 MB DDR
Creative Labs Sound Blaster Live! 5.1 PCI Sound Card (SB0220)
Samsung CD-RW/DVD Drive Model: TS-H492A/RSWN
Dual Boot openSUSE Linux 10.3/Windows XP Pro SP3
CodeWeavers CrossOver Games for Linux Version 7.1.2
I was also able to successfully install the official Version 1.1 Patch (contractjack_update_en_10_11.exe).
After initially using a Win98 bottle for installation, the game would not start after the patch was applied saying that the CD could not be found in spite of the fact that CD #1 was still in the same drive used for installation. I then installed the game in a WinXP bottle, and this particular problem went away. When running the game executable in the WinXP bottle, the launcher launches correctly. However, when the Display option is selected, "DX8 Renderer" is listed in the Renderers box, but there are no entries in the Displays box or in the Resolutions box. Under Windows 98 SE with a GeForce4 Ti-4200 card, I see "NVIDIA GeForce4 Ti 4200 (NVDD32.DLL)" in the Displays box and the following resolutions in the Resolutions box:
1024x768x32
1152x864x32
1280x960x32
640x480x32
800x600x32
960x720x32
If the Play option is selected, the launcher disappears, the CD-ROM drive is accessed, and there is hard drive activity. A pop-up dialog box appears with the following:
Contract Jack
A hardware TnL device was unable to be created. This could be due to either not having DirectX 8.1 installed or not having a hardware TnL capable video card. Both of these are required to play Contract Jack and although you can continue to play the game by pressing OK, please note that it is not officially supported and may result in crashes, lockups, and poor performance.
If you click OK at this point, another pop-up appears:
Contract J.A.C.K. <2>
Error initializing the renderer. In order to play Contract Jack you must have DirectX 8.1 installed.
Click OK and the application terminates.
So it seems that Wine/CrossOver isn't presenting an acceptable renderer option to the game as is the case in NOLF 2: A Spy in H.A.R.M.'s Way. If this problem can be resolved in one game, it will likely be resolve in the other game as well (the game is from the same developer, Monolith, and was released shortly after NOLF2).