By Wednesday night, Lilly had agreed to a four-year, $40 million deal with the Cubs, leaving Andy Pettitte as the Yankees' top pitching target.
"He just decided, at this point in his career, he would like the challenge of pitching in the National League," said Lilly's agent, Larry O'Brien. "He came up with Montreal and pitched a short time, but now he has a great opportunity. He thinks the National League will be suited to the way he pitches."
O'Brien informed the Blue Jays early Wednesday that the pitcher had narrowed his choices down to the Yankees and Cubs, eliminating Toronto from the sweepstakes.
The Cubs had made a "firm offer" to O'Brien, who was waiting to speak with Cashman again on Wednesday before presenting the final options to Lilly. O'Brien and Cashman spoke shortly before the agent's self-imposed 6 p.m. deadline, but no official offer was made. It was clear at that time that Lilly's future was on the North Side of Chicago.
"Brian just wasn't in a position to commit," O'Brien said. "Even if Brian would have committed and the numbers had been identical, Ted is probably still a Cub. At the end of the day, Ted really thinks they have a great opportunity to go from last to first. Detroit did it, why not Chicago?"
Pettitte's agent, Randy Hendricks, said in an e-mail Wednesday that Pettitte is planning to play next season, putting him in play for the Yankees to pursue. Pettitte would be an attractive option, as he would only be seeking a one- or two-year deal, though Hendricks said there was no timetable for Pettitte to sign.
"He has decided to play," Hendricks said in an e-mail, confirming an Associated Press report.
Lilly pitched for the Yankees from 2000-02, going 8-12 in 42 games, 32 of which were starts. The left-hander, who turns 31 next month, is 59-58 with a 4.60 ERA over parts of eight seasons with the Expos, Yankees, A's and Blue Jays.
Had the Yankees committed $40 million to Lilly, it would have actually cost them $56 million when the luxury tax is figured in. Cashman said that while he has approached this year's free-agent market "with caution," he won't be scared off by the luxury-tax issues if he believes the move makes sense for his team.
"I'd prefer to not pay that tax, but there's nothing I can do to prevent it," Cashman said. "If we have an interest in a player, whether it's on the free-agent market or acquiring a contract, we're going to pay it. Will it preclude me from doing things? Not necessarily; but it does factor into evaluations and decision-making."
"We had our first discussion," Cashman said. "There will be a few more before we get to, hopefully, what we both want."
As players continue to be plucked from the free-agent market, Cashman said that there is more urgency throughout the league to get deals consummated. For Cashman, the urgency isn't whether to sign a player, but whether to make a multimillion-dollar offer to any of the players on the market.
"People have to make their decisions," the general manager said. "Players want to know where they're going to play. They have offers they're weighing and they have to make a decision. The urgency from my end would be, 'Do I want to participate and put forth a solid offer for these guys to consider or not?'"
In Lilly's case, the answer was no.
Cashman said he was "pessimistic" that he would get anything done before he flew home to New York on Thursday.
"Things can change," Cashman said. "We'll see. I guess it's possible."
The Yankees, who signed Raul Chavez to a Minor League contract to compete for the backup catcher job, are still in need of a utility infielder and possibly a first baseman, but Cashman stressed that his current focus is solely on pitching.
"The rest of it will take care of itself over time," Cashman said.
With Chien-Ming Wang, Mike Mussina, Randy Johnson, Carl Pavano and potentially Igawa in the rotation, as well as in-house possibilities such as Scott Proctor, Darrell Rasner, Jeff Karstens, Phil Hughes and Humberto Sanchez, Cashman is in a position to sit back and wait for the right move to come along -- or to stand pat with what he currently has on his roster.
"I don't necessarily have to sign another pitcher," Cashman said. "We have inventory here. If we get a guy, that's fine, but I'm not going to worry about whether we can sign two. I'm focused on [whether] there's one that makes sense right now."
Mark Feinsand is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.