NEW YORK -- GM Brian Cashman will meet with New York Yankees co-owners Hal and Hank Steinbrenner on Monday in Tampa as the Yankees try to figure out how to win World Series No. 28 next season.
The meetings are expected to take two days, but could go longer. Later in the week, in New York, Cashman will also gather with his scouts to determine the best course of action in terms of which players the Yankees should keep and which they should go after.
Atop the agenda will be how to proceed with Derek Jeter. Jeter, who just ended his 10-year, $189 million contract, can become a free agent for the first time in his career five days after the World Series ends.
Cashman has already said publicly that he is only interested in paying players for how much they are worth in the win column. Cashman views Jeter as the Yankees best option at shortstop for next year, but the question is how many seasons after that?
Cashman said he doesn't put any monetary value on milestones. Jeter is likely going to become the first Yankee with 3,000 hits.
The negotiations are interesting because there is the shadow of Alex Rodriguez's contract hanging over the festivities. A-Rod's contract goes through 2017 and has bonuses if A-Rod breaks certain home run marks. Jeter has meant so much more to the organization, but it is hard to imagine him coming close to Rodriguez's current 10-year deal that could be worth up to $300 million.
The Yankees will also have to figure out how much they should offer Mariano Rivera. Rivera, 40, seems ageless. He is likely going to top the largest salary for a closer, $15 million, which is what he made last year. The question here is also the amount of years that Rivera will want and what the Yankees are willing to give him.
The next big piece that the Yankees will need to consider is how much to spend for Cliff Lee? Lee is undoubtedly their No. 1 offseason free agent target, but the Yankees must be careful that if they give Lee too many years their return on investment might not be as high as it would seem.
Lee, paired with a healthy CC Sabathia, seems like an unstoppable playoff force, but the Yankees must figure out how many years to offer Lee. Lee turns 33 in August of next season, so they have to consider how they think he will age. The Yankees and the Texas Rangers are the two favorites for Lee, but they could be joined by five or six other teams in the bidding.
This week, Cashman will gain a clearer view from ownership of what they are willing to pay in salaries. Last season, the team had a payroll of $210 million. The Yankees will also figure out which lefty reliever they would like to pursue to pair with Boone Logan.
Andrew Marchand covers the Yankees for ESPNNewYork.com.