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Chicago Cubs Winter Meetings preview

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The Cubs might not have a lot of needs this winter, but the current front office isn’t content with what they have.

Photo by Jonathan Daniel/Getty Images

The giant swap meet that is the MLB Winter Meetings start on Monday in Las Vegas at the Mandalay Bay Resort and the Cubs will be looking to kick start their offseason that has been pretty sleepy up to this point.

Fans tend to look at the Winter Meetings as something akin to Black Friday for baseball. It’s the time when their favorite team needs to get a head start on their Opening Day roster for the next year. This feeling is reinforced by things like the wall-to-wall coverage of the Winter Meetings on the MLB Network and honestly, articles like this one. In reality, the importance of the Winter Meetings has been decreasing in recent years. Decades ago, when teams could only communicate with each other through a bulky telephone attached to a cord that they had to rotate a dial to operate, the Winter Meetings provided the opportunity for general managers to talk to each other and with agents face-to-face. That’s less important these days as front offices are in constant communications with each other through email and texts, as well as the occasional cell phone call.

Still, teams start to feel pressure to make a move in early December, least they get shut out of the best players. The Cubs will feel some extra pressure to make a move to counter the Cardinals trade for Paul Goldschmidt. And while it seems like fewer deals get made at the Winter Meetings every year, there are still always a few big deals that get done at the winter. Maybe the Cubs will be involved in on of them.

It has been said that team president Theo Epstein does not like to stand still. He’s always looking at a way to make a big splash that he thinks will improve the team. That’s why there are some possibilities mentioned here that may be unlikely, but Epstein’s desire to be bold means no one should rule them out.

With that said, here are some things to look for out of the Cubs front office next week.

Looking to land a big fish

There have been a lot of reports that the Cubs don’t have enough money in the budget to sign either of the two big free agents, Manny Machado or Bryce Harper. There have also been a lot of people speculating that those reports are simply the Cubs playing possum.

No matter what the reports say on the Cubs payroll, everyone agrees that the Cubs have at least spoken with Harper’s agent Scott Boras this winter. How serious they’ve been is unclear, but the Cubs’ front office would be committing malpractice to at least not talk with Harper and Machado.

I don’t expect for either Harper or Machado to sign with a team next week. But we should get a better sense of whether the Cubs are really interested in signing Harper or Machado or whether they’re just going through the motions.

Backup backstop

I’m not quite sure what it means that the Cubs biggest need this winter is a backup catcher. Manager Joe Maddon doesn’t seem to trust Victor Caratini to handle the job and it doesn’t sound like the front office disagrees. There also seems to be a general feeling that Willson Contreras had a down year because he didn’t get enough days off.

The top free agent catcher on the market is Yasmani Grandal, who checks off all the boxes on what the Cubs’ front office is looking for. He can get on base, hit for power and despite his postseason meltdown, he’s usually a terrific defensive catcher. On top of that, he ranked as the best pitch-framing catcher in the majors last season whereas Contreras ranked as the worst.

The problem is that Grandal probably isn’t going to sign with a team where he’d be sharing time behind the plate. That would likely mean a trade of Contreras and then the Cubs would still need a backup catcher. Grandal also received a qualifying offer, so if the Cubs signed him, they’d lose a draft pick.

Still, if Epstein wants to make a bold move without signing Harper or Machado, this is a possibility.

A more likely target for a backup catcher is Martin Maldonado, who is a very good defensive catcher and a solid pitch framer. His bat is below average, but it sounds like the Cubs are more interested in a strong defensive catcher to pair with Contreras. But with the new emphasis on defense behind the plate, there will be a lot of teams interested in the services of Maldonado.

Jonathan Lucroy is another possibility as a free agent, although his defense has declined in recent years. He’s still a better pitch framer than Contreras, however, and he’d likely sign a one-year deal.

There’s always the possibility of a trade, but other than J.T. Realmuto, there don’t seem to be many catchers available on the trade market. The Marlins almost certainly want more for Realmuto in trade than the Cubs likely have or are willing to part with.

That’s a relief

The Cubs bullpen last season was pretty decent until a series of injuries left it bare by season’s end. Closer Brandon Morrow was very good in the first half of the season and didn’t pitch at all in the second half. Pedro Strop and Carl Edwards Jr. also missed time. Additionally, left-handers Jesse Chavez and Justin Wilson became free agents and Chavez has already signed with the Rangers. If Mike Montgomery stays in the rotation, then the only left-handers in the bullpen are Brian Duensing and Randy Rosario.

Left-hander Andrew Miller is a free agent who Cubs fans are very familiar with from the 2016 World Series. Unfortunately (or maybe fortunately), Miller didn’t have a very good 2018. The good news is that he won’t command a big deal like he would have had he been a free agent after 2016 or 2017. The downside of this is that it’s very possible that years of a heavy workload out of the bullpen could mean that his best days are behind him.

Tony Sipp is another free agent left-handed reliever who had a very good 2018, but that’s coming after poor efforts the two previous seasons. Lefty Zach Britton was perhaps the best reliever in the majors from 2014 until he suffered a torn Achilles in 2017. He hasn’t been the same since, although he’s still solid. But the recent trends and injuries mean a multi-year deal would be risky.

Of course, the Cubs could always trade for reliever. And speaking of that. . .

Make a big splash

As mentioned earlier, Theo Epstein hates to stand still and he never wants his team’s lineup to grow stale. That’s why I think he will at least try to make a huge splash and deal either Ian Happ or Kyle Schwarber next week. The Cubs have a lot of outfielders and it only makes sense that they try to deal one.

Both players are coming off mildly disappointing seasons, which is why the Cubs might want to hang on to both of them until they rebuild some value. But the two of them are the Cubs biggest trade chips and if Epstein wants to acquire an impact veteran, he’s going to have to part with one of them. Royals second baseman Whit Merrifield is the obvious target here. Although Merrifield didn’t reach the majors until he turned 27, he’s put up 11 bWAR over the past two and a half seasons. The Royals are rebuilding and might be interested in the younger Happ or Schwarber to build around. Acquiring Merrifield would mean the Cubs could move on from Addison Russell. Speaking of which . . .

Addison Russell

There’s been a lot written about Russell on these digital pages over the past few months. All I will add here is that if Epstein gets even a half-serious offer for Russell, he’ll likely take it. Especially if he can get someone to play second base and move Javier Baez permanently to shortstop.

The Cubs would likely accept any reasonable offer for Tyler Chatwood as well, but for totally different reasons. I don’t expect that they’ll get one.

Shopping at the outlet mall

There are some interesting free agents out there that aren’t named Machado or Harper. These guys aren’t cheap, but they won’t command deals of over five years and $100 million either.

Marwin Gonzalez is a former Cubs farmhand who has actually been almost as good as Machado over the past two years. He’s also got a defensive versatility that Machado lacks as Gonzalez has played every position in the majors except pitcher and catcher. However, a lot of teams are going to want Gonzalez and he won’t come cheap. He also turns 30 before Opening Day and free agent players over 30 are always risky. On the other hand, Gonzalez has been compared to Ben Zobrist in the past and the Cubs signing Zobrist past 30 turned out just fine.

If the Cubs do trade Happ or Schwarber, I wouldn’t be surprised if they tried to sign Andrew McCutchen for outfield depth. McCutchen isn’t anywhere near the player he once was, but he’s still solid and he probably won’t get more than a three-year deal in free agency, if that. Plus, he’s a terrific clubhouse presence and the Cubs would love to add someone with his leadership skills to the mix. The fact that signing McCutchen would drive Pirates fans nuts is just an added bonus.

We’ll have an overall league-wide preview of the Winter Meetings here on Sunday.