I think he missed the boat by not picking Brice or Dan. Both would have done well with this task because both seemed very sports-minded. Michael also would have been good because he really supported Lee. And all had experience equal to Lenny's in a much better package.
If I had to pick, I would have run straight to Tyrek. I wouldn't have given Sean a chance to get him because he is smart. Then, I'd have gotten Bryce on board. If he HAD to get a female, I'd have gone with Allie becazuse she's more creative. Roxanne is smart, but she's too analytical. Allie is a more creative type, and she'd have been great with the celebrities.
Who cares if Lenny would take a bullet for Lee? If he can't get the job done, loyalty is lost on him. Besides, Lenny did semi-attack Lee for going to Temple and missing his second task because of religious obligations.
Lee missed the boat by choosing loyalty over substance. If he ever truly had a shot, it left the building when he picked his team.