Captain Jack was completed in the summer of 2014. By some measures, it stands as probably the toughest trail at Mt. Crested Butte and one of the toughest downhills in the valley. Since it's completion it has claimed numerous crashes in the steep and rocky downhill and also has been a new measuring stick in the valley for downhill technical skill.
If starting from the top of the red lady lift, take the Upper Westside
trail out until you hit the Silver Queen road. When you're at the Silver Queen road switchback after Upper Westside
take the right split in the road which is just left of the Upper Westside
trail sign for the continuation of the trail. Do not turn immediately right when you get to the road. After a short ways you'll see the start ramp and a sign for Captain Jack.
The trail starts with 2 ramps. One of them is the start ramp and the second comes soon after which is a ramp to cross over the top of the Upper Westside
trail. The trail is fairly mild with the occasional root/rock for the first quarter mile or so. After this you'll come to a junction in the trail with a sign reading "Easier Route". Don't get this fool you as both routes are tough, steep and rocky. Choose your poison and use caution here. If you get through the first rock garden, stay on your toes as you'll have a few steeper moves, some tight trees and tricky rock moves after this. Once past the tough areas the trail gets milder with the occasional steeper section. Toward the end the trail joins up with the last part of Avery
near the lower jumps.