Key Storylines For Cubs As Winter Meetings Open

The Cubs are in dire need of a leadoff man.

Bruce Levine
December 05, 2019 - 3:12 pm

(670 The Score) The Cubs have many question marks as they head to San Diego for the Winter Meetings next week. 

Will they trade one of their core players as they look to revamp their roster? Just how active will they be in free agency given their budget constraints? Will they compete at the highest level in 2020 or will it be a season of transition?

The Cubs currently have just north of $180 million committed to 17 players for their 2020 roster, and they're looking to fill out the rest.

Let's look at a few key storylines for the Cubs with the Winter Meetings around the corner and a key stretch of the offseason upon them.

Find a leadoff man

The Cubs need to fortify their leadoff spot and in center field, and the best way to do that would be to trade for an experienced player who fills both needs.

Pirates outfielder Starling Marte would be an ideal fit. He's under contract control through 2021 at a total of $24 million and is coming off a season in which he hit .295 with 23 homers, 25 steals, a .342 on-base percentage and an .845 OPS. Marte is also a quality defender who has a career .341 on-base percentage.

The two teams are division rivals, but the Pirates are in a different phase of competitiveness than the Cubs, leaving open the possibility of a trade.

Braves outfielder Ender Inciarte could be another option. He's owed $16.4 million over the next two years, with a team option for 2022. He has a career .338 on-base percentage. He's also a quality defender who stole a combined 50 bases in 2017-'18 before he was slowed by injury in 2019. 

Royals second baseman/outfielder Whit Merrifield would be a quality fit as well. It's unclear if the Royals have him on the trade market, but they have new ownership that may be looking to make changes. Merrifield is on a team-friendly deal through 2023 and has a .344 career on-base percentage. He's also coming off an All-Star campaign in 2019.

Free agency offers few good options for the Cubs to address their needs at leadoff and in center field. Kevin Pillar was non-tendered by the Giants on Monday. He's a fine defender but has only a career .296 on-base percentage with a .701 OPS. He wouldn't fit as a leadoff man for the Cubs. 

Many of the other free-agent options -- such as Billy Hamilton, Jarrod Dyson, Keon Broxton and Juan Lagares -- are also weak offensively.

The Cubs have previously shown interest in Japanese outfielder Shogo Akiyama, a five-time All-Star in Nippon Professional Baseball. Akiyama has a career .376 on-base percentage in nine seasons for the Seibu Lions.

Who's at the back end of the rotation, bullpen?

The Cubs have a void at the No. 5 spot in their rotation after left-hander Cole Hamels left for the Braves in free agency, and they also need to add bullpen depth in the form of some swing-and-miss relievers who have good velocity. 

Either veteran right-hander Tyler Chatwood or 24-year-old right-hander Adbert Alzolay could be the answer at the back end of the rotation. Chatwood had a bounce-back 2019 season after a disastrous 2018, and he has the swing-and-miss stuff the Cubs want if he can find a way to more consistently harness it. Alzolay also has good stuff, though his inexperience and durability is a concern. 

The Cubs could also look to add a young starting pitcher in a trade.

Work on extensions with current players

The Cubs will discuss a long-term extension with star shortstop Javier Baez and his representation at the Winter Meetings, according to multiple reports. Baez is a crucial player for reasons beyond his elite talent and production. 

Having just turned 27, Baez is just entering his prime and hasn't hit his peak yet. He affects the game with his defense, baserunning and baseball savvy even when he goes through hitting slumps. Baez has two years of contract control left. If the Cubs could sign him to a long-term deal, it would be a statement to the rest of their core players of their importance as the heartbeat of the team and to the organization's commitment to competing at the highest level for years to come.

Third baseman Kris Bryant, first baseman Anthony Rizzo and outfielder Kyle Schwarber all can test free agency after 2021 as well, while catcher Willson Contreras is under team control through 2022.

How many $30-million-a-year players the Cubs can afford is a question they'll have to answer soon enough, and we could get a peek at the answer this offseason.

Quick dump and retool?

It's possible president of baseball operations Theo Epstein and the Cubs front office will look to accomplish what the Yankees did in 2016 and the ensuing offseason with a dump-and-retool approach in the span of a year.

If the Cubs were to trade a star like Bryant or Rizzo, that would bring back a supply of MLB-ready (or nearly ready) young talent. The thought process behind that would be to take a step backward for 2020 with an eye on strengthening the team's long-term prospects -- while also carrying the knowledge that the Cubs would be losing the said player in free agency soon enough.

Parting ways with Bryant or Rizzo would be painful for the Cubs, as both were central figures on their iconic World Series-winning team in 2016. That said, it may be time for big change from the Cubs with payroll tight and their minor league solutions sparse.

Bruce Levine covers the Cubs and White Sox for 670 The Score. Follow him on Twitter @MLBBruceLevine​.