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.

Cubs and Jake Arrieta reportedly have differing opinions on length of potential deal

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USA TODAY

Cubs and Jake Arrieta reportedly have differing opinions on length of potential deal

It seems the Cubs want to keep Jake Arrieta on the North Side — but maybe not for as long as the free-agent pitcher is hoping.

According to a report from FanRag's Jon Heyman, the Cubs met with Arrieta at the general manager meetings earlier this offseason. But, per Heyman, the two parties have differing ideas on how long a potential contract should be: Arrieta is said to want a lengthy six- or seven-year deal, while the Cubs would prefer to lock Arrieta up for a shorter period of time. Heyman added that the two sides probably haven't talked since.

None of that information comes as much of surprise, of course. Arrieta has been one of the National League's top pitcher over the past three seasons and is arguably the top arm on this winter's free-agent market. Guys fitting that description usually look to sign a long-term deal.

But one can certainly understand why the Cubs might be hesitating to give Arrieta that kind of contract. Arrieta, after all, will be 32 on Opening Day of the 2018 season and would be 38 in the final year of a hypothetical seven-year contract. Pitchers who retain elite status into their late 30s are few and far between.

And, as good as Arrieta's been over the past three seasons — helping the Cubs win the 2016 World Series and reach three consecutive NL Championship Series — his numbers took a bit of a downturn last season. He posted a 3.53 ERA with 163 strikeouts in 30 starts in 2017 after turning in a 3.10 ERA and 190 strikeouts in 31 starts in 2016 and a 1.77 ERA and 236 strikeouts in 33 starts during the 2015 season, when he won the NL Cy Young Award.

Still, all of those numbers are very good. The Cubs know what Arrieta can do and how important he's been to three straight playoff teams, and they have obvious needs in their starting rotation, with only Jon Lester, Kyle Hendricks and Jose Quintana locked into Joe Maddon's starting five for 2018.

These are things that Theo Epstein's front office will be weighing throughout the offseason, whether revolving around talks with Arrieta, any other free-agent pitcher or in trade talks with other clubs.

For now, it appears the Cubs would like to have Arrieta back. But will the two sides resolve their differences and get a deal done? Or is there another team out there more willing to give Arrieta the kind of deal he wants? That obviously remains to be seen.

Shohei Ohtani: Theo Epstein's White Whale

Shohei Ohtani: Theo Epstein's White Whale

In July of 2016, with his Chicago Cubs in the midst of an epic season, team president Theo Epstein had two simple words written on a board in the baseball operations offices at Wrigley Field: 

FIND PITCHING.

His team had the game’s best rotation at that time with stars like Jake Arrieta and Jon Lester headlining a group of arms that Epstein, GM Jed Hoyer and their staff had acquired since they arrived in Chicago in 2011. But Epstein knew that sooner, rather than later, the Cubs would need to add significant starting pitching to their organization if the Cubs were going to go on a run of contending for multiple World Series titles.

As the glow of the 2016 World Series title faded and the 2017 season kicked into gear, Epstein and Hoyer again turned their attention to finding high level starting pitching, which is the hardest commodity to stockpile in baseball. As the 2017 season turned towards the All-Star break, the Cubs stunned the baseball world by trading two of their best prospects to the crosstown White Sox in exchange for highly dependable lefty Jose Quintana who was a solid addition to the Cubs rotation and under contract through the 2020 season, giving the Cubs 3/5 of their rotation (plus Lester and Kyle Hendricks) under team control for three more seasons.

Now, as the baseball winter meetings get ready to commence in Orlando, Fla. on Dec. 9, the Cubs are looking to add two high-level arms to fill out their rotation. While there are a few attractive options in free agency such as Alex Cobb (Tampa Bay), Lance Lynn (St. Louis) and Yu Darvish (LA Dodgers), there is no one at the level of Japanese sensation Shohei Ohtani who is not only the best available pitcher in the world, but is also considered a high-level offensive player with 30+ HR potential. 

Multiple MLB scouts — including one rival front office executive — spoke with me regarding Ohtani with all of them concurring that Ohtani is indeed the real deal: 

“Remember the time you first watched a superstar player and you just knew he was going to be great? That’s what this kid is," the front office executive told me. "There is no way he isn’t going to be a superstar. He has all of the qualities that a player needs to be a success."

Ohtani is a true No. 1 starter with elite velocity that has reached 102 mph in the latter stages of his starts. He has a five-pitch mix at various speeds that make him very tough to game plan for. 

“Shohei can blow you away at 100 mph and he can make you look ridiculous with a breaking ball at 88," said an MLB scout who has watched Ohtani play over 50 times. "He can also sit somewhere in between and throw ANY of his pitches for a strike at varying speeds. Whoever gets him has a true ace who is only 23 years old and should be an instant star."

MLB sources have confirmed to me that the Cubs have spent significant time and money in their pursuit of Ohtani. The club has sent multiple scouts to Japan for weeks at a time and they have watched him pitch and play the outfield and they believe he can indeed do both on the north side of Chicago. 

A rival NL executive who has scouted Ohtani believes the Cubs will be on the short list of teams that have a realistic chance of signing him:

“Theo has been fascinated by this kid for a long time," the executive said. "He and Jed have been strategizing on how to land him in Chicago. They have the support system needed to make this work. They landed Daisuke Matsuzaka when he was in Boston and they have a good relationship with Ohtani’s agent (Nez Balelo) at CAA. 

"They are definitely one of the teams on his short list. But will he end up in the National League? That’s the big challenge.” 

The buzz in the baseball world has only a handful of teams with a real chance to land the franchise-changing star with the Yankees, Dodgers, Cubs, Red Sox, Mariners, Rangers and Blue Jays all considered possible landing spots. However, with Ohtani insistent on spending some time playing a position (either OF or DH) some in the game believe that favors an AL team.

So is this kid that good that NL teams are willing to allow him to pitch and play the OF for them? 

"The dude throws 100 mph consistently," former MLB outfielder Jonny Gomes — who played in Japan and saw Ohtani firsthand — told MLB Network Radio. "That plays. If you have the arm speed to throw 100 mph, guess what your slider's gonna do — yikes. And he also has a split, which is yikes with that arm speed. And he also has a changeup, and he also has a curveball. You're talking about five plus-plus-plus pitches.

"If he was in the draft, I think it would be a no-brainer right now that he'd be No. 1 overall."

What about Ohtani’s offensive potential and how it could translate to Major League Baseball? 

In 2017, Ohtani hit .332 with eight home runs in 65 games. The OF/DH sports a .286/.358/.500 career slash line with 48 home runs. 

"Now hitting-wise, is it gonna transfer, or is it not?," Gomes said. "I've seen the dude hit a fly ball that hit the roof of the Tokyo Dome. So, what does that tell you? That bat speed's there, that power’s there, that he's generating a lot out front.

"To be able to hit the roof of the Tokyo Dome is way more impressive than hitting any other roof in the states. It would be like hitting the roof in Seattle when it was closed, it's way up there."

Ohtani will have a major cultural adjustment coming from Japan to the United States, but he will also have a major adjustment transitioning into a veteran-laden major league locker room. Gomes believe that will be no problem for the 23 year old superstar. 

"I'm a big fan of the dude," Gomes told MLB Network. "I saw his work ethic, I saw how players treated him, I saw how respectful he was. Over there, it's all about seniority. Granted, he was the biggest star on the field at any given moment, but he still gave the utmost respect to seniority guys on his ball club."

Ohtani is also not about landing the highest contract at this point in his career. The Cubs and Dodgers are handicapped by having only $300,000 available to spend on an international signing while the Texas Rangers have $3.5 million dollars they can offer. 

“Shohei will probably make $20-30 million dollars in endorsements once he signs with an MLB team so whatever a team can offer him to sign right now is really irrelevant," an MLB executive said. "The kid is not about getting the last dollar. He doesn’t run the streets, he doesn’t party, all he is in love with is baseball. He is a phenomenal young man in every way which makes him a perfect fit wherever he signs.”