Several points here.
First, did you check to see if the player is willing to play with you? Send a coach call and see if you're listed as a "backup" option- if he tells you something like "I'd move on..." or "you have no shot" then you CANNOT get the player no matter what you do.
Second, if you can get him, check WOTS and see if the player is listed as "tight" with the sim team or something similar. If he is, then it will be a lot more difficult to get the guy. If it says he's "Open to other offers" or "not sold" or anything like that, then it will be much easier.
Third, if the guy is "open or "not sold", check your budget and try to anticipate how much you will need to spend elsewhere (like other battles, players you still want, etc). If you've got the budget, then you may be able to get the guy.
It usually takes multiple scouting trips to pull the guy down, and depending upon the sim's budget, a few HVs or CVs to take the lead.