The Chicago Cubs are one of the most fascinating teams to watch this offseason.

After a frustrating finish in the NL Wild Card, expectations remain high for this win-now group heading into 2027. At the same time, there is no ignoring some of the glaring roster holes that need to be filled. What they decided to do on the mound will be the biggest storyline to follow, which is why it feels like the perfect place to start today's round of offseason notes!

Let's get into a few Cubs notes you may have missed over the last couple of days.

Javier Assad's Option

According to Jordan Bastian of MLB.com, the Chicago Cubs have declined Javier Assad's option for the 2027 season. The versatile righty had a $3.3 million team option for next season but will now play under a new deal.

While this kind of news normally makes it sound as if a player is headed for free agency, that fortunately isn't the case for Assad. He will remain under team control due to arbitration and is projected to be a member of the Cubs' 40-man roster again next season.

So, why did they even decline the player option? The deal Assad signs through arbitration will be less than the $3.3 million he would have been owed. It might not be a major difference, but it's clearly enough for the Cubs to make the cost-saving move worth it.

Not to mention, all money matters in an offseason like this. The Cubs may be flush with cash, but all signs point toward them making several major roster moves. They have to add plenty of upgrades to both the bullpen and starting rotation – let alone figure out who will be their future starting options in the corners.

With that said, Assad should be an option for Craig Counsell in 2027. He may not have put together a true breakout yet, but he was rock solid in whatever role the Cubs asked him to play. He threw a 3.63 ERA in 28 games played, which included 11 starts. A solid innings-eater, Assad could be a good back-of-rotation arm if the Cubs end up going after one of the biggest star starters on the market. If they decide to share the wealth among a couple of new starters, then having him in the bullpen would be a fine compromise.

Speaking of which ...

Wanting Multiple Pitchers

Ken Rosenthal joined Foul Territory to talk about the MLB offseason, and he clarified some of the Chicago Cubs' pitching plans.

“I’m not sure the internal options are sufficient," Rosenthal said regarding Chicago's starting pitching options. "So, yes, they will be active in the market. I think they will sign or acquire two starting pitchers. One good thing in their favor is that the market is fairly deep, not in great starters, but starters.”

Of course, the Cubs have a wide-open rotation heading into the 2027 campaign. They have seen Shota Imanaga, Kevin Gausman, Clay Holmes, and David Peterson hit free agency. Matthew Boyd also chose to turn down his team option, while Jed Hoyer chose not to pick up Colin Rea's option.

The good news is that this gives the Cubs a ton of flexibility and money to spend. The bad news is that it also puts a lot of pressure on them to spend wisely. For what it's worth, Rosenthal does not think that spending will include throwing a franchise-record contract at Tarik Skubal, who was connected to the Cubs again earlier this week.

It's also worth noting that Rosenthal used the term "acquired." Is it more likely than not that Chicago uses their cash to sign a pair of starters off the free agent market? Yes, as there are plenty of options. But we all know the trade market can be just as busy during the winter, and this is a Cubs team that has not hesitated to strike deals for pitching over the last year-plus. Could the Seattle Mariners be on Jed Hoyer's radar, especially now that they have a former front office face as their manager?

No matter how they go about things, Rosenthal's words are just another reminder that it will be a very active offseason for Chicago in the pitching department. There will likely be a couple of guys re-signed, but expect to see several new veteran faces on the Opening Day roster.

Tyler Austin's Uncertain Future

The Chicago Cubs decided to outright Tyler Austin to Triple-A Iowa this week, officially putting his future in question.

A handful of North Siders are likely unaware of Austin's name. He didn't appear in a single Cubs game this season due to having right knee surgery. The expectation, however, was that he would compete for real playing time after initially agreeing to return to the Majors in December.

Austin was a former New York Yankees high-ranking prospect who spent two seasons seeing limited action in the Bronx before playing for the Twins, Giants, and Brewers. He never quite found his groove in the Bigs, which led him to head overseas to join the Yokohama DeNA BayStars of the Nippon Professional Baseball league.

Austin would go on to have quite the strong career, playing for the BayStars from 2020 to 2025. He would become a true power threat, crushing 85 homers and tallying 236 RBIs. Overall, during his six seasons of play, Austin slashed .293/.569/.377.

Obviously, there was no guarantee that he'd find similar success at the MLB level, especially at 35 years old, but it was a fascinating depth gamble for the Cubs. All things considered, that's why it will be interesting to see what happens from here. Do they stick with Austin and see if he can finally carve out a bench role in 2027, or do they simply part ways after the failed experiment?