Chicago Cubs: Three free agents the team should go after this winter

(Photo by Jonathan Daniel/Getty Images)
(Photo by Jonathan Daniel/Getty Images)
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(Photo by Jonathan Daniel/Getty Images)
(Photo by Jonathan Daniel/Getty Images) /

Looking to balance out a lineup that’s become too one-dimensional, the Chicago Cubs have an opportunity to make big changes via free agency this year.

On the surface, the Chicago Cubs were a pretty solid ball club in 2019. They ranked fifth in the league in runs scored, fourth in on-base percentage and second in home runs, setting a new franchise record by blasting 256 long-balls on the year.

But all that resulted in a disappointing 84-win season and missing the postseason for the first time in nearly half a decade. The front office moved on from Joe Maddon and kicked off a search that remains ongoing here in late October.

As I’ve said before – the theme of this offseason will undoubtedly be change. The scope of said change remains to be seen. But it seems safe to assume the team that takes the field on Opening Day next March will look quite different from the one we’ve grown used to in recent years. 

With the World Series underway, obviously, the true hot stove season hasn’t even kicked off yet. Still, it’s never too early to kick around some names – especially given the Cubs’ needs at second base, in the outfield and in the bullpen.

(Photo by Todd Kirkland/Getty Images)
(Photo by Todd Kirkland/Getty Images) /

Chicago Cubs: Will the team bring some rain to the hot corner?

This is a tough sell, I know. Josh Donaldson reestablished his value in a big way this year with Atlanta, appearing in 155 games and putting up a .901 OPS. He represented the perfect mix of power and patience, drawing 100 walks for the second time in his career while hitting 37 home runs.

Coming off this one-year deal with the Braves, Donaldson will undoubtedly have plenty of suitors this winter. If the cards fall right, the Chicago Cubs could be among those clubs. But, again, a lot would have to happen and major changes would have to take place to get it done.

Right now, the Cubs have franchise cornerstone Kris Bryant holding down the hot corner. After an injury plagued 2018 season, the former NL MVP returned to form this year – until an ankle injury ended his year prematurely. He didn’t drive in as many runs as you’d like to see, but given he hit second most of the year and the leadoff spot was a proverbial black hole, I don’t really blame him for that.

So the Cubs have some decisions here. If they were serious about Donaldson, they’d need to do one of two things with Bryant: trade him or have him move to the outfield full-time.

But there’s a potential problem with this plan. He’s a corner outfielder. So you’re either sliding Jason Heyward over to center and sticking Bryant in right or you’re seriously considering trading Schwarber, who is coming off one of the best offensive seasons of his young career.

Schwarber has made strides defensively, as well – he’s clearly more than a designated hitter at this point – despite what many fans may think. A Donaldson move definitely adds an on-base presence to the mix, but it might raise more questions than provide answers.

(Photo by Christian Petersen/Getty Images)
(Photo by Christian Petersen/Getty Images) /

Chicago Cubs: Flores turned in a solid campaign in Arizona last year

Contrary to the belief of new-age baseball fans, it’s not realistic to field a superstar at every position in Major League Baseball. You can come close, but it’s just not something you should expect from your team – even a large-market presence like the Cubs.

I wouldn’t be shocked at all if the team brought back Ben Zobrist as a key bench piece in 2020 – perhaps a one-year swan song to let him go out his way, rather than in a drama-riddled season that saw him battle personal matters off the field. If that’s the case, he can obviously play all over the diamond, including second base.

My top target is Howie Kendrick, despite his age. But given how well he’s performed in the postseason for the Washington Nationals, his asking price may be significantly higher than it was mere weeks ago. Knowing that, could Epstein pivot to a guy who will command less, such as Wilmer Flores?

Trust me, I know. This is the last name I ever thought I’d be writing about. To me, he’s still that young kid on the Mets who was an alright ballplayer, but nothing crazy special. But, to my surprise, he was pretty special as a member of the Arizona Diamondbacks in 2019.

Flores set career-highs in pretty much every offensive category. In 89 games, he slashed .317/.361/.487 – good for a 118 OPS+. In fact, this marked his fourth consecutive year of grading out as an above-average offensive player in terms of OPS+ and wRC+. So while this year was something of a break-out, he’s been solid for longer than I’d known.

I’m not saying he’s going to suddenly be an All-Star presence, but if the Cubs are going to make a big splash elsewhere, they may have to play it savvy at second base – and Flores fits the bill.

(Photo by Jonathan Daniel/Getty Images)
(Photo by Jonathan Daniel/Getty Images) /

Chicago Cubs: Castellanos makes a ton of sense for this team

In my lifetime, I don’t know if I’ve ever seen a midseason acquisition perform as well as Nicholas Castellanos did this summer. Without him, honestly, I don’t know if Chicago even breaks .500.

He brought a palpable energy and presence to the yard with him every day and the numbers speak for themselves. Post-trade, Castellanos turned in a 1.002 OPS with the Cubs, smacking 21 doubles and hitting 16 home runs in just 51 games. On the year, he narrowly missed becoming the first player with 60+ doubles since 1936.

But knowing all that, we also know one incredibly important fact: he’s going to get paid.

Castellanos represents one of the highest upside talents on the market this winter and given the show he put on in the middle of a playoff race for Chicago, it’s hard to find a team that won’t be intrigued by the possibility of adding him to their lineup for years to come.

The outfield is particularly intriguing for the Cubs. Heyward can play center or right, but is notably stronger defensively in right field. Adding Castellanos back means Heyward moves to center (assuming Schwarber returns, as well). That’s a clear upgrade over the likes of Albert Almora, but it’s still worth mulling over.

Next. These three players won't be on the 2020 roster. dark

Really, what it all comes down to – whether we’re talking outfield, bullpen or up the middle, is the Chicago Cubs are poised to have a ton of moving parts this winter. Where they all wind up will be the story of the offseason at the offices of Gallagher Way.

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