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?
MLB
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.