Cashman traveled to Arkansas to meet with the free-agent left-hander and his representative, Darek Braunecker, getting acquainted as the Yankees enter the early stages of a courtship that they hope will end with Lee trying on Yankees pinstripes.
The Yankees reached out to Lee almost immediately on Sunday, minutes after they were permitted to speak with him, as a way of demonstrating that the 32-year-old will be a top target this winter.
Cashman's trip to the city of Benton, Ark., represents another avenue for the Yankees to make their intentions clear. While the Yankees did not immediately slide a financial offer across the table to Lee, the discussions of dollars historically have quickly followed Cashman's in-person visits.
In December 2008, Cashman ducked out of the Winter Meetings in Las Vegas after two meetings with CC Sabathia and flew to the hurler's California home, with a seven-year, $161 million pact that he quickly signed with the Yankees.
Cashman also met with first baseman Mark Teixeira that winter as a courtesy, even though at the time, the Yankees were not thought to be leading the chase for the switch-hitting first baseman. But Teixeira impressed the Yankees in that meeting and he soon inked an eight-year, $180 million pact with New York, spurning his other suitors.
Several reports have indicated that Lee could be seeking a five- or six-year agreement, with an annual value approaching or exceeding the $23 million per season the Yankees are paying Sabathia.
The Rangers have also vowed that they will attempt to keep Lee, with CEO Chuck Greenberg and team president Nolan Ryan adamant that they will not allow the Yankees to swoop in for the hurler. Lee was a perfect 7-0 in the postseason before suffering two losses in the World Series against the Giants.
One topic Cashman may have addressed was an incident involving Lee's wife, Kristen, during the American League Championship Series at Yankee Stadium. She said that Yankees fans taunted, swore and spit at the players' wives seated in the visiting section, but Braunecker recently said that the incident is "not an issue to us."
Braunecker was quoted this week as saying that Lee will not be in any rush to make a decision. With no comparable choices on the free-agent pitching market, Lee may have the luxury to weigh offers until at least the Winter Meetings in December.
Lee was a combined 12-9 with a 3.18 ERA in 28 starts for the Mariners and Rangers, including seven complete games.
The Yankees attempted a power play for Lee in July, when the Mariners put him on the trade block, dangling a package anchored by power-hitting catching prospect Jesus Montero, only to see him traded to the Rangers instead.
New York's starting pitching could have used the upgrade, as the season turned out. Sabathia and Andy Pettitte pitched through injuries down the stretch, Phil Hughes stumbled in the playoffs and A.J. Burnett and Javier Vazquez were unreliable.
The Yankees' other offseason priorities include re-signing free agents Derek Jeter, Mariano Rivera and Pettitte. No contracts have been offered at this time, but Jeter and agent Casey Close met with managing general partner Hal Steinbrenner, team president Randy Levine and Cashman recently in Tampa, Fla., to discuss the situation.
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.