As hard as it may be to watch, the Chicago Cubs should be locked in on the World Series. Not only should it serve as a learning opportunity as they look to return to the championship round themselves, but you never know what opportunities may arise in free agency.

With plenty of money to spend, the Cubs are expected to be a serious player on the free-agent market in a matter of months. The Brewers and Rays may not be overflowing with available talent, but they each have at least one name who could be worth pursuing for the Cubs.

Let's go over a free-agent-to-be from each team that the Cubs should have their eye on this winter.

Freddy Peralta

Let's be honest, you already knew his name was coming!

Freddy Peralta has been connected to the Chicago Cubs for essentially the last year. Falling out of favor with the Milwaukee Brewers, the former ace was sent to the New York Mets in January as one of the winter's biggest transactions. What happened next, however, was something few could have predicted.

A star-studded New York team crumbled from the jump, and Peralta plummeted along with them. His production was down significantly, as he struggled to keep his ERA below 5.00 in 22 starts. His swing-and-miss stuff was non-existent, and his hard-hit rate continued to trend in the wrong direction. It instantly became clear that Peralta needed another change of scenery, which is why he was heavily tied to the Cubs as the trade deadline loomed.

Indeed, the safest bet a few months back was that Peralta would finish the year on the North Side. Not only did the Cubs have a clear need, but Craig Counsell had a strong relationship with the former All-Star from their time in Milwaukee. Nevertheless, it was the Tampa Bay Rays that swooped in to grab Peralta, and it didn't take long for them to fix him.

In his ten starts with the Rays, Peralta held a far more recognizable 3.25 ERA. His allowed slugging percentage dropped from .448 to a much more manageable .330, while his walk numbers also improved significantly. Peralta has now been nails for the Rays in the postseason, appearing in four games total and throwing a 1.08 ERA in 16.2 innings. He's allowed just 2 earned runs and has struck out 12.

There is no question that this will catch the eye of rotation-needy teams, and we all know the Cubs fall into the "rotation-needy" category. To be sure, Peralta would be a departure from the kind of pitcher the Cubs typically pursue, as he is built around generating whiffs as opposed to ground balls. Not to mention, he does have a tendency to walk his fair share of batters. But the upside and experience are blatantly clear!

Chicago has needed a shake-up on the mound for a while. Peralta would offer them something different with his fastball-heavy approach, as well as give them the kind of proven postseason production they desperately need.

Brandon Woodruff

Would the Chicago Cubs consider stealing a fan-favorite from their long-time rival?

Brandon Woodruff has been a thorn in the Cubs' side for many years. He has been one of the Brewers' top arms ever since the late 2010s, putting together two All-Star campaigns and recording a career ERA of 3.10.

Woodruff was on a familiar pace this season, starting nine games with a 2.98 ERA. His K rate sat at an impressive 27.0 percent, while his command remained elite with just a 5.7 walk percentage.

What is arguably most impressive about Woodruff is that he was able to completely reinvent his game following a serious injury. He missed all of 2024 due to shoulder surgery, eventually returning with less velocity on his fastball but more devastation on his off-speed stuff.

Still, like Peralta, Woodruff would offer the Cubs the kind of strikeout stuff they have lacked for a long time. The playoff production also can't be ignored, as he has appeared in the postseason four different times, with this year potentially serving as his fifth.

The big question with Woodruff is whether the Cubs want to risk injury trouble. He has had countless setbacks with his shoulder over the years, which will make investing in him a major risk for most organizations. The Cubs, in particular, have already had plenty of bad injury luck with their rotation, which could make Woodruff even less appealing.

At the same time, whenever Woodruff has taken the mound, he has been pretty darn great. There is also a chance that adding him doesn't come at too steep a price, making it a lower-risk, higher-reward opportunity.

For what it's worth, I would envision the Cubs signing Peralta well before they add Woodruff into the mix. But the Cubs' pitching issues also run deep, and you never quite know how the market will turn out. At this point, we just can't rule anything out.