NEW YORK -- When the clock strikes midnight late Saturday night, Derek Jeter will turn into a free agent.
Barring a last minute agreement, the 36-year-old Jeter will enter free agency for the first time in his career and will be able to negotiate with any of the major league teams. If Jeter can find a team that will give him close to what the New York Yankees will offer, he could create some leverage.
However, it is basically impossible to find anyone in baseball who thinks that there is another team that will outbid the Yankees or even come close to what New York will offer. Ultimately, after what could be some tense moments, Jeter is expected to return as the captain of the Yankees.
The issue is for how long and how much. While the Yankees gave Alex Rodriguez a contract that will take him until he is 42, they are expected to try to restrict Jeter's deal to three years at most. Jeter would be 39 at the end of such a contract.
"I could see him getting three-plus a club option for a fourth from the Yankees," an AL executive said.
At midnight, the Yankees can also start to execute the romancing of their top target, Cliff Lee.
The Yankees are expected to be one of about seven or eight teams that will go after Lee. The Yankees and the Texas Rangers are considered the favorites. Lee Sweepstakes likely will last until December Winter Meetings.
Jeter is coming off a 10-year, $189 million deal so even though he won't find a market that will pay him $20 million per year, the Yankees may give him that much because of what he has meant to the team and the city. The Yankees could ultimately be thinking to end at about three years and $60 million.
If the Yankees give Jeter his money, they may also have a conversation with him in which they explain to him that over the life of this deal if he doesn't perform they will move him off short and down in the lineup. After signing his own new contract last week, Yankees manager Joe Girardi declined to rule out demoting Jeter out of the top spot in the lineup.
In 2010, Jeter led off for most of this season, but hit a career-low .270. In the ALCS, he failed to reach base to open up the Yankees' half of the first in any of the six games.
Both sides likely hope for a quick resolution to the Jeter situation. If
negotiations go as long as the Lee courtship, then Yankees owner Hal Steinbrenner will likely prove prophetic when he recently said that talks could become "messy."
Andrew Marchand covers the Yankees for ESPNNewYork.com.