Alex Cobb

The 3 biggest Cubs questions as MLB Winter Meetings kick off

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USA TODAY

The 3 biggest Cubs questions as MLB Winter Meetings kick off

LAKE BUENA VISTA, Fla. — As the baseball world descended upon Disney World, the Cubs are sitting pretty.

Theo Epstein's front office is poised to make "The Happiest Place on Earth" a reality as they already appear to have some of their major offseason issues resolved.

The Cubs reportedly have an agreement in place with late-inning reliever Brandon Morrow, a move that should be announced Monday once a physical is passed, the "I" are dotted and the "T"s are crossed. 

Couple that with last Thursday's signing of starting pitcher Tyler Chatwood and the Cubs' search for pitching has gone well even if they missed out on 23-year-old Japanese sensation Shohei Ohtani.

However, while the Cubs are in an enviable position of filling most of the pressing holes on their roster entering the MLB Winter Meetings, there are still questions to be answered.

Here are the top three questions facing Theo and Co. in Florida this week:

1. Who will fill the final rotation spot?

The Cubs are said to be pushing hard for Alex Cobb to fill out their starting staff, but as of the official tipoff of the Winter Meetings, no deal had been reached.

Cobb and the Cubs have been linked since before the right-hander even reached free agency. There was a clear need for another starter on Chicago's North Side heading into the winter and Cobb had the connection with Joe Maddon from their days together in Tampa Bay.

Cobb's connection to the Cubs was strengthened when Maddon hired former Rays pitching coach Jim Hickey to serve in the same role in Chicago.

If the Cubs are able to secure Cobb's services, they will have their starting rotation set for 2018:

Jon Lester
Kyle Hendricks
Jose Quintana
Alex Cobb
Tyler Chatwood

Depending on the length of the deal for Cobb, the Cubs could have some rotation consistency for the next several seasons as all four current starters (Lester, Hendricks, Quintana, Chatwood) are signed through the 2020 season.

However, if the Cubs and Cobb can't come to an agreement — they are hardly the only team bidding on the 30-year-old's services — who will be the fifth and final starter? The free agent market is rather slim after Cobb, Jake Arrieta and Yu Darvish, though the trade market is clearly an option with the Cubs currently possessing a surplus of young position players.

2. Will the Cubs pull off any major trades?

There's no doubt the Cubs will be linked to plenty of trade rumors throughout the week at Disney World, but will anything actually come to fruition?

Kyle Schwarber has been linked to a pair of American League East teams — the New York Yankees and Boston Red Sox — over the last few days, but it'd be tough to see the Cubs sell low on a guy they absolutely love.

Forget the fact that he's lost a bunch of weight and in the best shape of his life (which does matter if he's to improve his range in the outfield), here's how Epstein explained why the Cubs feel such a personal attachment to America's Now-Not-So-Large Adult Son:

"I will say that it's really an organization-wide evaluation of this player," Epstein said the day after the Los Angeles Dodgers eliminated the Cubs from the NLCS in October. "But I'm not skirting responsbility. I'll happily endorse him. He's the type of the player that we want to win here with the Cubs and have won with. 

"The fact that he hit 30 bombs in a bad year is a good start. But power is not everything. I think he fell into this year becoming a little bit more of a slugger and less of a hitter than he really is. That's important for him to get his identity back as a hitter, as a dangerous hitter that honestly, we feel he has the potential to be an all-around hitter on the level of Anthony Rizzo, per se. 

"When he reaches his prime, I think we feel like that's what he could be. He's got certain toughness and certain leadership qualities that are hard to find that we don't necessarily have in surplus in abundance running around in this clubhouse and organization. Certain energy and grit and ability to bring people together. That's important. We rely on it. But the biggest thing is his bat. We think he's the type of offensive player that you build around along with a couple other guys like him."

You'll be hard-pressed to find a better public endorsement of any player from Epstein.

But even if Schwarber isn't dealt, the Cubs can still trade any number of guys from a pool that includes Ian Happ, Albert Almora Jr., Javy Baez or Addison Russell.

3. Will Morrow have any other new bullpen mates?

Assuming Morrow's deal doesn't hit any snags, will the Cubs add any other relief reinforcements this week?

It's a pretty good bet to take. Never in the history of baseball have relievers had such an impact on important games — particularly in October — and the Cubs clearly understand that as well as anybody.

After Maddon's mix-and-match approach with the bullpen the last two postseasons, the Cubs clearly cannot go into 2018 with World Series expectations when they boast essentially the same relief corps, with Morrow replacing Wade Davis.

Speaking of Davis, the presence of Morrow doesn't necessarily mean the 2017 Cubs closer with "huge balls" won't be returning. Morrow's reported $10+ million per year makes a Davis return less likely, but the Cubs certainly need another impact reliever and Morrow can slot in as a seventh/eighth inning setup guy.

Here's how the Cubs bullpen depth chart looks right now (with Morrow inserted):

Brandon Morrow
Carl Edwards Jr.
Pedro Strop
Mike Montgomery
Justin Wilson
Justin Grimm
Dario Alvarez

Plenty of high-leverage relief options remain available on the open market, including Brandon Kintzler (whom the Cubs were linked to this week), Addison Reed, Anthony Swarzak, Jake McGee and Bryan Shaw.

New report suggests Cubs likely to pursue Rays All-Star pitchers Chris Archer and Alex Colome

New report suggests Cubs likely to pursue Rays All-Star pitchers Chris Archer and Alex Colome

The Cubs might be looking to bring a little bit of Florida sunshine to the North Side this winter.

Already rumored to be interested in signing free-agent pitcher Alex Cobb — something that might be a tad less likely after signing starting pitcher Tyler Chatwood a few days ago — a new report Saturday indicated the Cubs are likely to pursue a trade with Cobb's old team, the Tampa Bay Rays, in an attempt to secure the pitching services of Chris Archer and Alex Colome.

There's always been plenty of "what if" surrounding Archer and the Cubs, who dealt the right-hander away back in 2011 as part of the deal that brought Matt Garza to Chicago. Archer has been on plenty of fan wish lists over the years, too, as he's had a great run in his six big league seasons with the Rays, making a pair of All-Star appearances, posting a career 3.63 ERA and making at least 32 starts in each of the last four seasons.

Archer's numbers have been slightly less appealing in the past two years, a combined 4.05 ERA in 2016 and 2017 after turning in a combined 3.28 ERA in 2014 and 2015. But he's still just 29 years old and considered one of the game's better arms.

Colome, meanwhile, led baseball with 47 saves last season and has saved a combined 84 games over the past two campaigns. He was an All Star in 2016, and he finished that season with a pencil-thin 1.91 ERA.

Archer is under team control through 2021, while Colome is under team control through 2020.

Certainly the Cubs are in the market for another starting pitcher and a closer thanks to the free-agent departures of Jake Arrieta, John Lackey and Wade Davis. Losing Arrieta and Lackey put a significant hole in the starting rotation, though the signing of Chatwood filled one of those two open spots. The Cubs are shorter on options when it comes to a ninth-inning man. They've been connected to free-agent relievers Brandon Morrow and Brandon Kintzler this offseason, and there's the potential option of bringing Davis back on a new contract, one that figures to be expensive after he converted 32 of 33 save opportunities in 2017.

Archer and Colome would knock two huge items off Theo Epstein's offseason to-do list. But as Rogers mentioned, it will likely take a big-time return package to net a couple of All-Star pitchers. The Cubs' minor league system has been seriously depleted in recent years as many of the organization's biggest names have either reached the big leagues — helping the team to that curse-smashing World Series win in 2016 — or been traded away in midseason deals for Aroldis Chapman and Jose Quintana in the last two years. That means it'd likely take multiple guys on the major league roster to acquire Archer and/or Colome. The same names that have been speculated about this offseason would once more figure to come into play in this discussion: Kyle Schwarber and Ian Happ. But perhaps Javier Baez and others would be needed to swing a deal like this, too.

Of course, the Cubs would figure to have tremendous scouting reports on Archer and Colome — and Cobb, for that matter — with not only Joe Maddon's history in St. Petersburg, but also with Jim Hickey now on Maddon's staff as the Cubs' new pitching coach. Hickey came to Chicago this offseason after 11 seasons with Tampa Bay.

It remains to be seen if anything comes of this at the Winter Meetings, which begin Monday in Florida, or later on this offseason. Certainly starting pitcher and closer are two areas of need for the Cubs, but they might not have the assets to pull off a trade of such magnitude.

Cubs Talk Podcast: Cubs aiming for Alex Cobb while remaining in the Ohtani sweepstakes

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USA TODAY

Cubs Talk Podcast: Cubs aiming for Alex Cobb while remaining in the Ohtani sweepstakes

David Kaplan and Eric Strobel are joined by Tampa Bay Times beat writer Marc Topkin to discuss potential Cubs pitching targets Alex Cobb and Chris Archer, and Topkin reveals why new Cubs pitching coach Jim Hickey is known as a sorcerer within baseball circles.

In addition, Kelly Crull is joined by John Harper of the New York Daily News who has proposed a potential trade sending Kyle Schwarber to the Bronx.

Plus, we break down the field as the Shohei Ohtani sweepstakes begins to wind down.

Listen to the full Cubs Talk Podcast right here: