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Does "buying UFA years" drive up cap hits?

One common phrase that's popped up during the interminable wait for the contract extensions for Calgary Flames wünderkinds Johnny Gaudreau and Sean Monahan is "buying UFA years." The concept is this: in a player's first contract after their entry-level deal there are two kinds of deals, short-term "bridges" and long-term deals. The theory is that as a contract goes longer and stretches into the years in which that player would otherwise be an unrestricted free agent (UFA), the deal's cap hit will go up.

But is that what actually happens? And more precisely, does the number of UFA years covered in a post entry-level deal make much of a difference?