Simple answer: No.
In order to deduct medical expenses, you must be the person who paid the medical expenses. Even then, the person you paid the medical expenses for must be yourself, your spouse or your dependent. There is an exception: you may deduct medical expenses for someone who would qualify as your dependent, except for the fact that they have more than $4200 of reportable income.
Even then, medical expenses are only an itemized deduction, subject to the 7.5% of AGI threshold. Also, to be deductible, medical insurance premiums must be paid on an "after tax" basis. So, it would further depend on what "his check" is.