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What it will take to close the Epstein deal

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What it will take to close the Epstein deal

Sometime within the next 48 hours, Theo Epstein is expected to smile for the cameras.

With flashbulbs popping all around the stadium club, Epstein will pose for the before picture at the news conference where the Cubs will introduce him as their next head of baseball operations.

The after picture whether Epsteins hair turns gray or the stress of the job starts to show on his youthful face could be telling. This city demands nothing less than another World Series title from the 37-year-old executive.

What it will take for the Cubs and Red Sox to close this deal is gradually coming into focus. High-ranking officials from both sides remained underground over the weekend. On both days there were SUVs parked in the reserved spots for employees near the entrance to Wrigley Fields administrative offices.

As much as Cubs chairman Tom Ricketts and team president Crane Kenney would no doubt like to take a victory lap, there remains the matter of compensation, what it will take to pry Epstein from the final year of his contract.

Its also unclear if Epstein will be able to bring any Red Sox staffers along with him to Chicago. Sources continue to insist that Brett Jackson is untouchable and not part of the discussions.

Jackson generated 20 homers, 58 RBI, 21 stolen bases and a .379 on-base percentage in 115 games split between Double-A Tennessee and Triple-A Iowa last season. The Cubs believe that their 2009 first-round pick out of Cal-Berkeley could make the big-league club out of spring training.

The Red Sox are believed to be focused on Trey McNutt, a 22-year-old right-hander who is arguably the organizations best pitching prospect. The 32nd-round pick seemingly came out of nowhere (Haleyville, Ala.) in 2010 and went 10-1 with a 2.48 ERA and 132 strikeouts in 116.1 innings.

McNutt dealt with injuries in 2011 and didnt really build off that breakout season, finishing at 5-6 with a 4.55 ERA at Tennessee. But theres still enough upside where the Cubs could think hed eventually be part of their 2012 staff and refuse to give in to Bostons demands.

Either way, it will likely take two prospects. The Marlins set that baseline when they lured Ozzie Guillen from the South Side to South Beach.

A source familiar with the negotiations said that the Cubs are reluctant to give up anyone wholl be on their 40-man roster this winter. In that sense, Josh Vitters and Matt Szczur are viewed as unlikely to be included in the deal.

Vitters, the third overall pick in the 2007 draft, has been slower to develop. But hes still only 22 and team officials believe hes maturing.

Vitters is currently playing in the Arizona Fall League after hitting .283 with 14 homers and 81 RBI at Tennessee. He could probably use a full season on the Triple-A level in 2012. The Cubs will risk losing him if they dont sign him to the 40-man roster.

Szczur, a two-sport star at Villanova, has a unique contract that requires him to be moved to the 40-man roster this offseason. That was part of the recruiting pitch to give up his NFL ambitions and focus only on baseball. The 22-year-old outfielder finished last season at Class-A Daytona.

While the Red Sox examine the system, they will find intriguing players from the 2011 draft. Ricketts told his scouting department to take chances last summer and find more impact players. The chairman authorized close to 12 million in bonuses.

Those players cannot be traded until a year after the day they signed their contracts. In theory, a player could be labeled to be announced in the final Epstein settlement. But the Red Sox wouldnt want to take on the injury risk or stash him at a Cubs affiliate for almost the entire 2012 season.

A source predicted that the Red Sox will play this exactly like the agents at the signing deadline, waiting until the last minute to get the best possible deal for their clients.

There was no rush to hold a press conference on Sunday, with the Bears playing in primetime and the New England Patriots and Dallas Cowboys featured in another marquee game. Why compete with the NFL for attention?

A harder deadline will come before Wednesday, when the World Series begins and Major League Baseball forbids teams from making formal announcements. There are no games scheduled for Tuesday, and then commissioner Bud Selig imposes his news blackout.

While the tone of these negotiations made headlines, the big picture is that the Cubs and Red Sox have already found so much common ground. There is a motivated buyer and a determined seller. Everyone agrees that Epstein now belongs in Chicago.

Cubs Talk Podcast: MLB Insider Jeff Passan talks about Cubs offseason plan

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USA TODAY

Cubs Talk Podcast: MLB Insider Jeff Passan talks about Cubs offseason plan

02:00 Jeff Passan predicts a significant trade or two for the Cubs this winter

03:00 Passan says the Cubs will be retooling, not rebuilding, because they still have good players

04:00 Kris Bryant and Willson Contreras are the most likley to be traded

05:00 Passan explains the perception of Contreras around the league

07:00 How active will the Cubs be in free agency?

08:00 Any chance the DH will come to the NL soon?

09:00 What would a Cubs team with Anthony Rendon look like (even though it's very unlikely)

12:00 What are you more disappointed in? The haul the Cubs gave up to the White Sox or the results they have gotten from Jose Quintana?

19:00 Is Willson Contreras the most likely Cubs player to be traded this winter?

21:00 If the DH is eventually coming to the National League, is it worth hanging on to Kyle Schwarber even longer?

Listen to the full podcast here or via the embedded player below:

Cubs Talk Podcast

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Be ready for anything: Cubs open to all trade avenues this winter

Be ready for anything: Cubs open to all trade avenues this winter

While Cubs fans sit on the edge of their seats waiting to see if Theo Epstein's front office trades away a core player — and which guy that might be — the question has really become more of a when

Both because it seems likely Epstein shakes up this Cubs roster this winter and because there's natural curiosity about the timing of such a move. 

If the Cubs don't get the type of return they're seeking for players like Willson Contreras and Kris Bryant, they are not going to trade just for trade's sake. But it's clear the roster needs a change and the front office has also shifted a good amount of focus on the long-term future of the organization — beyond 2021, when most of the core players are set to hit free agency.

As for when a major trade may come down, there's really no indication on that front. The MLB Hot Stove season has taken longer and longer to get going in recent winters and that very much appears to be the case again this 2019-20 offseason as many teams — including the Cubs — have just recently finalized their coaching staff and key front office hires.

At the GM Meetings last week, the Cubs said they were in the early stages of any offseason moves and had just started to exchange names with other teams about who is and isn't available.

They're not pigeonholing themselves into any one avenue for how the winter will play out.

"Sometimes you get a feel for the marketplace or kernels of ideas and they end up coming true and you look back and you're like, 'ah, that feel we had really matched the whole tenor of the offseason with certain teams,'" Epstein said. "Other times, you can go through a whole Russian novel's worth of twists and turns in an offseason depending on one or two player moves or clubs changing course or being able to execute things or not execute things. 

"We'll see. I think the important thing is to keep a really open mind and be prepared for all different permutations of how things can work out."

As for what shape the trades may come in, be ready for anything. 

The Cubs have said they still have no issues trading within the division, so even in a year where they're planning on competing in the wide-open NL Central, they're more concerned with improving their organization in the long run than worrying about potentially making a rival better.

Epstein also said they're not afraid of acquiring a player with only one year of team control left, as long as it makes sense. But there's no reason right now for the Cubs to mortgage the future to go all-in on 2020.

"It just depends on the player and the fit and the acquisition cost, and everything else," Epstein said. "I think we're like every team — to one extent or another, we're trying to balance an immediate future vs. a longer-term future. We knew that as we got closer to the end of the period of club control with some of our best players, we had to be increasingly mindful of if you put the longer-term future rather than just the short-term. 

"It's a bit of a transition for us, but it doesn't mean you rule anything out, even if it's something short-term. But you try to strike that right balance."

The Cubs also insist they're not locked into adding any one specific position or type of player. For example, they're not only looking to trade for centerfielders or leadoff guys — even if both are clear areas of need in the short-term.

Anything is on the table, which makes sense considering trading a core guy would also open up a hole elsewhere on the roster. If Contreras is dealt, the Cubs could feel pretty confident about Victor Caratini sliding into a larger role, but they would obviously need more catching depth both in the short- and long-term.

"I still think we have a lot of pieces that can move around the board a bit," Jed Hoyer said. "As we think about what we're gonna do [and] have conversations the whole winter, there's a big picture element to it where I think we're not gonna be entirely married to this position or that position — making moves that make sense both long-term and short-term. 

"We do have pieces that you can move around that makes us able to do that. We don't have particular holes that we feel like we have to spend the whole winter trying to fill, but rather we can make some moves maybe a little bit more strategically."

So the Cubs are saying all the right things, but what does that mean? 

For starters, it doesn't appear any major move is approaching on the horizon and regardless of what the first trade or free agent signing is, it will be just one piece to a larger puzzle. This is shaping up to be a crucial offseason in every aspect of the organization, so the final judgement of the winter will be the most important one.

But as the Cubs try to put that puzzle together and make their big-picture plans a reality, they're not going to get sidetracked by the incessant rumors and aim to continue trying to shield their players from a similar fate.

"We can't chase down every rumor," Hoyer said. "People are gonna put stuff out there about our guys and there's definitely some clickbait opportunity about our guys. We have a lot of guys who have been All-Stars and you can put a story out pretty easily that gets clicks. 

"One of the things about our players in general is we're in a big market, they're used to having their name in trade rumors, they're used to having their names out there. I think they have a sense of what's real and what's not real. But we can't chase down every rumor. We can't deny every rumor because we know that's going to happen. We have to live with that. We're not gonna add fuel to that fire, that's for sure." 

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