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I had a D-6B 44A series with oil clutch which I suspect has similar clutch brake to your D-7. the clutch brake should be accessed by removing the floor board panels above the clutch housing. (This should be the area near the dash board and rear of the engine). There is a short driveshaft between the clutch housing and transmission and a brake hub on this driveshaft. Actuate the clutch lever back and forth and you should see movement of the clutch brake shoe and spring on the upper left of this brake hub. Whereas you pull the clutch lever back toward you to engage the clutch, you actually push the clutch lever forward away from you to engage the clutch brake. If the brake shoe does not engage and stop the driveline from turning when you push the lever then you need to turn the adjuster screw in the spring to get the proper engagement between the shoe and hub. Unfortunately, it has been 20 years since I owned my D-6 so my memory may be faulty. (Or your 14A may have a different set-up). My machine was hydraulic blade and I suspect that your cable blade winch only works when the hand clutch is engaged. Conversely, with the clutch lever disengaged, then engaging the winch control may serve to stop the transmission shaft from rotating just like the clutch brake does. So in the short term, you may find that engaging the blade lift may help you get the transmission into gear before you engage the clutch. Obviously, this is not a long term solution and you need the clutch brake adjusted or relined, but is is an interesting thing to try. If this does not work and no one else comes to your aid then post this request on the Antique Caterpillar Machinery Owner Club web site (acmoc.com). Heck, some one there may even post illustrations from service manual for your. Best wishes and good luck.
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