Towers also indicated that a third team would be needed to facilitate a deal and possibly even a fourth team and that a deal, if it's agreed upon, wouldn't be announced until after Thursday's Rule 5 Draft.
The Phillies are believed to be the third team involved in the deal and have the pitching that the Padres would want in return. The Cubs have been rumored to be amenable to sending second baseman Mark DeRosa to the Phillies, who would then send pitching the Padres' way.
The Padres could also recoup pitching from a fourth team, like the Orioles, as they've been linked to left-hander Garrett Olson for the last month.
Towers said the package of players he's looking at lean more toward pitchers than position players and toward Major League-ready players who could land on the 25-man roster for Opening Day instead of prospects.
Towers had the sense that Hendry needed to move "money first" in order to get the deal off the ground. That could mean moving pitcher Jason Marquis and his $9.875 million contract for 2009 and possibly another player.
As was the case Monday, Towers is waiting to hear from Hendry that the deal is a go before they can proceed any further.
"We've pretty much settled on the players coming back," Towers said. "Jim has a feel for what we need to move Peavy. It's 'Is he able to make things happen financially to take on Jake's contract.'"
Peavy will make $11 million in 2009 and is owed $63 million over the next four seasons.
Still, Towers is moving ahead cautiously, knowing that moving Peavy in a deal will leave the Padres without their No. 1 starter and would net a return of players fans might not get excited about.
"If we make this decision to trade with the Cubs, we all better be damn happy with it," he said.
The Padres have been reluctant to move on any other fronts until the Peavy issue is resolved, which is why Towers has said he and Hendry have an agreement that there will be some resolution by Thursday.
While Towers has essentially figured out what he would be getting from a third team as well as a fourth team if needed, there's still some question as to what the Cubs would give in return. The prospect of pulling off a multi-team deal is daunting, Hendry said.
Since he became the Cubs' general manager, Hendry has been involved in one deal involving more than one team and that was when he acquired Nomar Garciaparra at the Trade Deadline in July 2004.
"We've only made one [multiteam deal] in my GM career, and that was a four-way and to this day, I'm not quite sure how it happened," Hendry said. "It was a two-way all week and all of a sudden, it became a four. I'm much better served one-on-one. I'm not quite as efficient as Theo [Epstein] or Billy Beane in multi-tasking, so I keep it as simple as I can."
Of course, some of the proposed compensation for Peavy could help fill the needs of a team that lost 99 games last season. In addition to looking for pitching, the Padres covet middle infield depth after trading Khalil Greene last week as well as a backup catcher.
The Padres are plotting their potential moves in Thursday's Rule 5 Draft, as they could take in upwards of three players, all likely pitchers to help aid a bullpen that went from the best in the Major Leagues in 2007 to among the most inconsistent last season.
San Diego will pick third in the Rule 5 Draft behind Washington and Seattle. The Padres currently have 37 players on their 40-man roster.