But even with a trade appearing to be the most viable option for Minnesota, exactly who the Twins would be willing to give up to get Jennings is questionable. Many pundits have pointed to the club's abundance of talented young arms as quality trade bait, but Ryan was quick to squash the notion that he may give up some of his pitching prospects.
"We don't have that much depth there," Ryan said. "If [Francisco] Liriano (out for the season) and [Brad] Radke (expected to retire) were still here, I'd say, 'Yeah, we have depth, but without them, we're not in a great position to get rid of young arms."
Team officials within other organizations also question Minnesota's willingness to part with its Minor League pitching depth. Without dealing young arms, it would then seem the club could possibly use its wealth of Major League bullpen talent as trade bait -- relievers Jesse Crain and Juan Rincon have also surfaced in trade rumors. Yet Ryan was quick to dismiss that idea, too.
"There is a reason that we have won a lot of games the last five or six years, and most of it goes back to the stability and consistency of the bullpen," Ryan said. "I think it would be wise that if you're going to go with some youth in the rotation, that you make sure you've got ample arms that you can count on in the bullpen."
That leaves the Twins pondering how to acquire the starter that they need. Without much money to spend, the top tier of this year's high-priced free-agent market doesn't seem a likely option for the club.
Instead, it appears that the Twins could be left trying to evaluate potential bargains in the lower rungs of this free-agent market. The type of pitcher that the Twins now could be seeking through a trade or free agency might be similar to the one they dealt away just this past season -- Kyle Lohse. At the time, it seemed best to move Lohse, but now the Twins are left without any sort of depth in the rotation.
Nevertheless, Ryan said he doesn't regret the move.
"I think it was time, and I think he'd agree," Ryan said. "We tried to make it work. In the end, I think both sides benefited from a change of scenery. He moved on, we moved on."
Pitching may be the club's top priority, but with an open slot in the lineup at designated hitter, the Twins have other items on their radar during these Winter Meetings. One name that could come into play is free agent Mike Piazza. The Twins appeared to have interest in Piazza last year when they were seeking a DH, and he's on the market once again, though reports have him linked to serious discussions with the Athletics.
Rondell White, who struggled with injuries and a subpar first half before helping the Twins down the stretch in 2006, could be brought back in the role. But Ryan says the Twins haven't had conversations with White, and the Twins appear set to to weigh all their options on the open market.
"There are players out there we have interest in and [White's] one of them," Ryan said. "We are keeping our options open."
So adding pieces to the club that won the American League Central title this past year is a goal, but it seems that not depleting the Twins' wealth of young talent is just as big a priority. The Twins would like to sign arbitration-eligible guys like Joe Mauer, Justin Morneau and Michael Cuddyer to long-term deals this offseason, and that work also begins this week at the event where many agents gather.
"We'll make inroads here regarding that," Ryan said. "It's something in-house that we've certainly looked at and considered already. We've tried to figure out what makes sense for us. But what makes sense for us often times doesn't make sense for the player."
The work might start for those contracts here at the Winter Meetings, but like everything that the club is currently seeking to do, it won't be something that the team believes will happen overnight.
"It's going to be a long process," Ryan said of the contracts. "It's not something that is going to come together in three or four days."