This much we should know: when it comes to getting David Ortiz [stats]'s name on a Red Sox [team stats] contract, nothing is easy.

With the team's window of exclusivity expiring at midnight tonight, it appears increasingly likely Ortiz will hit the open market.

Ortiz seeks a two-year contract believed to be worth between $25 million and $30 million. The Red Sox have shown a willingness to go multiple years with Ortiz, according to a source with knowledge of the negotiations, which leaves money as the sticking point.

Appearing last night on WEEI's Hot Stove show, general manager Ben Cherington said both sides want to reach a deal that keeps Ortiz in Boston, but hurdles remain.

"We've been talking to David since the end of the season, good conversations," Cherington said. "Everyone knows we'd like to keep him. I think there's mutual interest. We've had a lot of talks and we've made up some ground in some areas, but we still have some work to do. We'll keep working on it. If we get past (tonight), we'll continue to work on it. We remain hopeful we'll see him in a Red Sox uniform next year."

The Red Sox will almost certainly tender Ortiz a one-year qualifying offer of $13.3 million, which is the average of the top 125 salaries in the game. That guarantees they'll receive draft-pick compensation for Ortiz if he signs elsewhere, though the cost of another team signing such a player is steep.