NEW YORK -- The members of the Yankees' brain trust have sought many of their answers from the state of Florida during the winter months, so the upcoming Winter Meetings should serve as familiar ground.
When the wheels of general manager Brian Cashman's plane touch down in the Orlando, Fla., area -- just a short drive from the brass headquarters in Tampa, Fla., -- the preparations for what could be a crazy week will already be in order.
The Yankees will hit the Winter Meetings in Lake Buena Vista, Fla., with business to be done, having yet been unable to resolve many of the items that appeared on the to-do list when Alex Rodriguez looked at the final strike of the season.
Cliff Lee is the top priority outside the organization, and the Yankees are willing to pay top dollar to make sure that the left-hander puts on pinstripes, making him no longer available to damage their annual goal of winning the World Series.
"We certainly can play in the big sandbox more than anybody because we're the Yankees, but we certainly aren't successful every time we enter the process," Cashman said on the YES Network last week. "We're trying. I can tell you that."
And Lee's services figure to be on parade during the Winter Meetings, with agent Darek Braunecker feeling no need to drum up interest in his client, not during a winter when Lee is far and away the top starting pitcher on the market.
Cashman has already made preemptive moves to remind Lee that the Yankees would be pleased to have him. In November, at Braunecker's invitation, Cashman flew to Lee's Arkansas home for a getting-to-know-you session that transpired over lunch.
While no financial terms were swapped at that time, Cashman made sure to relax any concerns Lee might have about playing in New York -- especially after Lee's wife, Kristen, complained about fans who spit on the players' wives at Yankee Stadium during the American League Championship Series.
Braunecker has said that the ugly incident will not have any bearing on Lee's final choice, and while the Rangers are hopeful they can persuade the 32-year-old to stay, team president Nolan Ryan has already acknowledged that he doesn't believe Texas can outbid the Yankees.
The Yankees are believed to be preparing to at least make Lee the second-highest pitcher in the game, behind their own CC Sabathia, who signed a seven-year, $161 million contract before the 2009 season.
But adding Lee wouldn't be all for the Yankees, who continue to stand apart from free agent Derek Jeter in negotiations that -- to borrow a phrase from managing general partner Hal Steinbrenner -- have progressed in "messy" fashion.
While both sides seem to agree that the best possible outcome (and perhaps the only realistic one) is to have Jeter as the Yankees' Opening Day shortstop, actually getting that into writing has proven more difficult than some anticipated.
Jeter was not inclined to accept a three-year, $45 million proposal from the Yankees, which is the team's highest offer to date. Reports indicated that Jeter's agent, Casey Close, would prefer to get his client a five-year deal worth about $22 million to $24 million per year.
"I certainly don't envision, and never want to envision, Derek Jeter being anything but the New York Yankees' shortstop," Cashman said.
The Jeter negotiations have taken on a life of their own in New York, where callers have flooded to the airwaves in support of one side or the other. But the Jeter talks have also hovered over the rest of the Yankees' offseason work to be done.
That includes signing Mariano Rivera to a new deal -- the idea of a two-year contract worth about $18 million per year has been floated, with agent Fernando Cuza continuing to talk to the Yankees -- and also pursuing an answer from Andy Pettitte, who continues to dance with retirement.
It was during the Winter Meetings in December 2008 that Cashman stole the show, jetting out of Las Vegas secretly so he could personally deliver a record-setting deal to Sabathia's California doorstep.
Last year's Winter Meetings also had their busy moments, as the Yankees went in looking to retool a World Series-winning roster.
They left Indianapolis having pulled off a three-team trade to bring in center fielder Curtis Granderson and having re-signed Pettitte at the same time. It seems a safe bet that the Yankees will make their fair share of news at this gathering, too.
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.