If anyone was hoping for a quick resolution to Derek Jeter’s contract situation, think again. As the eighteenth day of the off-season begins, the Yankees and their captain remain ‘miles apart’ in terms of a new contract. As Joel Sherman reported yesterday, the Yankees are approaching negotiations with Jeter in a civil, business-type manner. The team is willing to pay Jeter more money per season for this contract, but will not go beyond three-years. Reportedly, Jeter is asking for a five or six year deal at his past rate (roughly $19 per season).

Outside of Jeter’s massive fan support, World Series rings, and unquestionable desire to win, sits the 800 pound gorilla in the room. Jeter’s 2010 season was arguably his worst season to date. Specifically, his batting average fell by 64 points and at times, he looked painfully slow playing shortstop. Jeter did take home another Gold Glove, but the Yankees know The Captain’s days are numbered.

Jeter’s glaringly poor 2010 season does hinder him a bit with negotiations, but a few unquestionable points stand out. Jeter is only 74 hits away from becoming the first Yankee ever to collect 3,000 hits. His popularity and fan appeal is unmatched in New York City. Jeter embodies everything that a Yankee should be:

A true gentleman who has the selfless desire and passion to help his team win.

Regardless of the parties involved, baseball contracts need to be smart decisions for both the player and team. The Yankees know they have to be smart with Jeter. Upsetting the captain could be a devastating PR move, but they also don’t want to get locked into an ugly five or six year contract with a declining shortstop who will need to move over to third base in the near future.

In the end, the Yankees and Jeter will agree to a new contract. However, we may end up ringing in 2011 before the Yankees ink up Mr. November.