With Derek Jeter and Mariano Rivera immediately becoming free agents and Cliff Lee spraying bubbly down the hall at Rangers Ballpark in Arlington, Cashman knew he'd have his hands full -- and there were no promises anything would move quickly.
"I think it's usually pretty obvious every year for the most part what our priorities are," Cashman said. "It's real simple, because you've got the closer and the shortstop that are a layup in terms of knowing, well -- they have to get done. And then after that, it's things you'd like to get done, but can you? Will you? We'll see."
Starting pitcher: The Yankees wasted no time in hammering home their interest to Lee, who is far and away regarded as the best free-agent starter this year. Cashman reached out to Lee's agent, Darek Braunecker, within minutes after he was permitted to, and also flew to Arkansas in November for a meet-and-greet. Lee is going to be the star of the Winter Meetings in Lake Buena Vista, Fla., and the Yankees will be in hot pursuit, battling the Rangers for his attention and prepared to flex their financial muscle. It is possible New York could approach the $23 million average it gave CC Sabathia in making him the game's highest-paid pitcher, offering Lee five or six years. It's a necessary expense after the Bombers' starting pitching flopped down the stretch and in the playoffs, damaging their bid to repeat as champions. They'd also love to get an answer from Andy Pettitte, who decided on a one-year contract during the Winter Meetings last year.
Shortstop: Everyone agrees that Jeter is probably going to be manning shortstop on Opening Day for the Yankees, but how do they get there? The Yankees' initial offer was three years and $45 million, and Jeter's camp is said to have been looking for five or six years at an average of $23 million per. Insert a few days of silence, some sharp words in the media and then a clearing-the-air session in Tampa, Fla. With some movement on each side, there's optimism they'll get it done, but it looks like Lee might actually make his decision before Jeter does -- something you would have bet against in October.
Closer: If you're going to sign a closer, it might as well be the best postseason performer of all-time. Like Jeter, there seems to be no danger of Rivera going elsewhere -- he couldn't keep a straight face during his last negotiations after the 2007 season, acknowledging he had no plans to leave. But the game goes on anyway, as Rivera seeks a modest raise over the $15 million he earned in '10, as well as perhaps a multiyear deal. Normally, you'd be wary of offering two seasons to a 41-year-old closer -- but Rivera's not a normal case.
Lefty reliever and setup man: Don't forget about the bullpen, which has been overshadowed while they work on bigger-ticket items. Boone Logan did a nice job as the Yankees' lone lefty for most of the year, but with Damaso Marte possibly out for all of 2011, the Yankees are in the market for another reliable southpaw. Kerry Wood slotted in to bridge the eighth inning after coming over from the Indians in a July 31 trade, but New York wasn't prepared to pick up an $11 million option for a setup man. The club still has interest in Wood at the right price, but after his performance down the stretch, Wood might be able to get good money to close elsewhere.
Backup catcher: This isn't a priority at the moment and probably won't happen during the Winter Meetings. But Cashman said he'd be willing to look into the free-agent market for a catcher, even though the Yankees are planning to have a trio of young prospects -- Jesus Montero, Francisco Cervelli and Austin Romine -- battle to catch during Spring Training. The idea is to have those three figure it out and allow Jorge Posada to see more time at designated hitter, but that's subject to change.
Who could be dangled on the trade market
Joba Chamberlain: As of now, the Yankees see the right-hander coming into camp looking to reclaim his role as the eighth-inning setup man -- a job he lost due to inconsistency. He's had his troubles bouncing between the rotation and the bullpen, but teams haven't forgotten Chamberlain's high-octane entrance into the big leagues in 2007. He could still provide an appealing trade chip if the right package comes along. Maybe another team would even try him in the rotation again.
Brett Gardner: The 27-year-old is slotted in as the Yankees' Opening Day left fielder, but if they're unable to sign Lee, it is possible they could reverse position and need to trade for a starting pitcher. If that's the case, Gardner seems more likely to be included than Curtis Granderson or Nick Swisher, positioning New York to join the free-agent chase for Carl Crawford -- something it hasn't shown serious interest in right now.
Montero: There's no reason to think the Yankees are going to start shopping Montero now, not after deflecting trade attention on him for years. But they were prepared to move him to the Mariners in July for Lee, so he's not exactly untouchable. New York figures Montero is big league ready as a catcher right now, and it sees him slugging in pinstripes. But until April rolls around, anything's possible.
Ivan Nova: Appearing in 10 games (seven starts) for the Yankees in 2010, he showed signs of promise and could figure into their rotation plans -- or he could serve as a useful trade chip if needed. The hard-throwing right-hander was 12-3 with a 2.86 ERA in 23 starts at Triple-A, winning 10 of his last 11 decisions there, but they also have other talented arms coming through the chain.
Montero, Romine, C Gary Sanchez, RHP Dellin Betances, LHP Manny Banuelos, RHP Andrew Brackman, RHP Hector Noesi, IF Eduardo Nunez, OF Slade Heathcott and IF Brandon Laird.
The Yankees are stacked at the catching position. Sanchez is further down the chain than Montero and Romine, but he's been praised as a promising offensive talent. Romine gets overshadowed because he doesn't have Montero's bat, but he's got the skills to make it as well. At some point, one of these backstops may be used as a trade chip to fill a need. Brackman was up in September and could make his big league debut at some point this year.
Big contracts they might unload
Chamberlain, RHP Phil Hughes, Logan, RHP Dustin Moseley.
Hal Steinbrenner has said the Yankees will "stay within the same level" from 2010, when they posted a Major League-high $206.3 million payroll. It's true the Bombers have the ability to play in the biggest sandbox, and they do take advantage of that. But even they have limits. Chunks of money came off the payroll in players like Javier Vazquez ($11.5 million) and Nick Johnson ($5.75 million), but New York is also theoretically putting money back into re-signing players like Jeter, Rivera and perhaps Pettitte. Several players (Granderson, Teixeira, Swisher and Robinson Cano among them) are also seeing pay bumps under their current contracts, so it would be a challenge to stay at or under their 2010 figure, especially if the Yanks are able to sign Lee.