So I did some research and you are correct on this. Most policies require a 60 to 90 day "deductible", basically. The team eats those first 2-3 months of the injury, then insurance covers a percentages of the rest - typically 50 to 80%. A couple interesting things I learned. One, these policies are expensive. On average about 10% of salary for a pitcher. Two, they often won't even cover pitchers elbow or shoulder, because those are so common. The Diamondbacks had made an offer to resign Brandon Webb, but retracted the offer when the insurance company refused to write a policy covering his right arm. So, for all we know the Twins may not even have insurance on Hughes.