Lester only one topic of note at winter meetings

As teams await Jon Lester's decision, trade talks could heat up at the winter meetings. Thearon W. Henderson/Getty Images

SAN DIEGO -- As the saga of free-agent pitcher Jon Lester presumably winds down to a final decision soon, the baseball offseason kicks into high gear at the winter meetings this week in southern California.

This is where both free-agent and trade talk will pick up, and industry sources continue to indicate the latter could provide the most interest outside of Lester’s decision.

Ironically, what makes the trade market so interesting is next year’s free-agent class. Widely accepted as one of the better classes in years, teams will have to make a call on whether to move a 2015-16 free agent now. If he’s going to leave next winter anyway, getting something for him now -- or at the July 31 trade deadline -- might be the best route to go.

“A reasonable observer would see there’s a lot of 5-plus (service time) pitchers available... because it becomes decision time,” Cubs President Theo Epstein said on Friday. “It’s one of the reasons we moved Jeff (Samardzija) when we did, to get ahead of that marketplace when we did. Offer a player with more than one year remaining and get a little better return.”

This is where the Cubs -- and other clubs -- might have some tough decisions. If Jordan Zimmerman, Johnny Cueto, Samardzija, David Price and many others can be had now via trade, should they pull the trigger? Just like the Cubs got ahead of the marketplace by trading Samardzija last July, they could get ahead of next year’s marketplace by trading for someone now. It potentially means giving up a prospect or more for a one-year rental. The St. Louis Cardinals just did that in trading pitcher Shelby Miller for free agent-to-be Jason Heyward. But the Cardinals are in a win-now mode trying to capitalize on the open windows of production that veteran players like Matt Holliday and Adam Wainwright possess. The Cubs aren’t quite there yet.

“There’s a time to trade for a 5-plus and there’s a time to wait,” Epstein said. “A lot of it depends on what the rest of your roster looks like, if you can retain that player and most importantly what the acquisition cost is.”

A trade and immediate contract extension would be the best-case scenario, but one of the most coveted moments in a player’s career is that time where he can shop his skills to every team in the league. How many (good) free agents have come away underpaid? Take Samardzija for example. It’s a near certainty he will be traded from the Oakland Athletics this winter as they have no chance of re-signing him. It’s also a near certainty that he’s a one-year rental for a team. He’s come too far -- and has too much self-confidence -- not to test free agency. Don’t rule out the possibility of the Cubs trading for a 5-plus player now, but it would have to be on their terms and their terms only.

Of course, things could change if they sign Lester. In a little bit of a surprise comment, Epstein indicated the offseason plan might change some if a stud player like the lefty pitcher comes to Chicago.

“When there is a potential impact player involved it does shape a little bit the course of your short-term thinking,” he said. “If you get a player that makes a significant difference for you in the standings then you prioritize creating a winning roster immediately around that player, whereas if the offseason goes in a slightly different direction you just continue to build more organically and continue to think more longer-term. It’s not an extreme, it’s not two absolutes but obviously you look at things a little bit different.”

Epstein is basically answering the “are things accelerated” question if they acquire an impact player like Lester. His statement may have been for Lester’s or other free agents' benefit as much as anything else. Nothing wrong with reminding the baseball world the Cubs want to compete as soon as possible. But in reality, it probably does not change the Cubs' plan all that much. As stated in this blog previously, the ironic part of the Cubs is that even though they don’t have a complete starting pitching staff right now, it’s their offense that remains a question mark.

“There’s never been pitching as good in the major leagues as there is right now,” Epstein said. “It is a very rare hitter that can step right in from the minor leagues and perform against modern pitching. There’s probably only three dozen hitters on the planet that can hit big league pitching consistently right now and make an impact. It’s that good, so it’s probably unreasonable to expect young players to step right in and dominate and fulfill any lofty projections.”

In other words, the Cubs will find the pitching but their hitting remains a development process from within. There is no downside to hoping the talented group of prospects the Cubs possess will progress quicker than the norm but hoping and expecting are two different things. And it’s not like they can realistically address their hitting via the marketplace either -- not without tearing down everything they just spent three years building. That would put them back to where they were when Epstein took over the Cubs.

“We were never under any illusions it was a great market for position players and the ones that were weren’t necessarily a great fit for us,” Epstein stated of this year’s class. “There’s a lot of volume in the pitching market. A lot of work remains to be done in that front.”

So we (somewhat) know the plan regarding pitching and with veteran hitters mostly off the market -- especially the one they wanted in Russell Martin -- where do the Cubs turn to help that offense? Their needs are fairly obvious.

“Bringing in position players who complement our expected position player group over the next few years,” Epstein said. “We’re pretty right-handed, that means left handed hitters are more attractive to us. We have more power than on-base skills so getting someone who has the chance to hit at the top of the order and gets on base will be a little more attractive to us. We have plenty of ‘swinging and miss,’ we don’t need more of that.”

The acquisition of infielder Tommy La Stella this offseason addressed that notion in a small way and it gave them insurance in case they want to make a bigger trade, perhaps with Luis Valbuena.

“There’s been a lot of interest in him,” Epstein said. “They’re realizing how good a player he’s been. It’s nice to see him getting his due. As other third baseman go off the board teams are realizing how valuable he is. Because we claimed him off waivers sometimes that creates a stigma for a player that he’s just a stop-gap so to speak. He will not be traded for a stop-gap price tag that’s for sure. He’s an important player to us. We value him highly.”

That brings us to the stickiest question of them all: Will the Cubs entertain trade proposals for All-Star shortstop Starlin Castro? If so, you would have to expect they would be done under a cloak of secrecy as this isn’t one of these “must-do” deals. There is a void of good shortstops in baseball and the Cubs have several middle infielders at different levels of their careers, including a top prospect in Addison Russell.

A Sunday CBS report says the Cubs are telling teams Castro isn't available but that doesn't mean they shouldn't explore all possibilities -- for now or the near future. The team would be foolish not to explore what they could get for either Castro or Russell. That just makes sense. Whether they actually pull the trigger on a deal is unknown but it should be looked into.

And that, in a nutshell, is what the winter meetings are all about: exploration.

“The actual talk to action will probably be 50/1,” Epstein said smiling.

But that one move could be the difference-maker for the Cubs. Maybe Lester signs with them this week and, if so, anything else they get done becomes gravy.

“We’re working on a lot of fronts,” Epstein said.

Backup plans if they miss out on Lester and looking for veteran help in the catching and outfield departments are probably on that list. Free agency still isn’t the No. 1 priority for the Cubs despite their pursuit of the former Red Sox lefty.

“I think there will be a time when we’re the feared team in free agency,” Epstein said. “We’re probably not at that time yet.

“We’re not the Dodgers or the Yankees but there are plenty of things we can do.”

This is the week to do some of them.