Red Sox: Past free agency mistakes make Dave Dombrowski cautious

Despite these risks, Dombrowski remains interested in Martinez’ bat, so long as he can be signed to a reasonable contract. The term “reasonable” should be used lightly for a player who could earn north of $25 million per season. It’s the length of the contract that matters most, with the Red Sox only looking to go as far as five years.

That offer is already on the table. This is typically the part where Boras would pit suitors against each other to drive up the price, yet a slow free agent market has left him short on teams to play his game. Any team would be thrilled to have a hitter of his caliber in their lineup but few teams have both the financial resources to afford him and a place to put him on the field.

Dombrowski knows what he’s willing to offer for Martinez and Boras believes he can get more for his client. The two sides remain at a stalemate waiting to see if another team will join in. Unless another serious suitor tops their current offer, Dombrowski would only be bidding against himself if he continued to push for a deal to get done. That’s essentially what happened to him in 2012, when desperation to fill a gaping hole in the lineup led him to overpay Fielder when no other team was offering a contract in the same ballpark.

Next: Swing, Misses, Foul Tips

He learned his lesson and Dombrowski isn’t going to be duped by Boras again. There’s no need to raise his bid when nobody else at the table has shown a willingness to call and most seem ready to fold.