The Cubs are in a great spot.

They entered the four-day All-Star break in first place in the NL Central with the best run differential (+119) in baseball and on pace for 96 wins.

If fans were presented that scenario before the season, they would have been ecstatic.

The other side of the coin does exist, however. The surging Milwaukee Brewers — winners of seven straight entering the break — are just a lone game behind the Cubs in the division race.

Those pesky neighbors to the north just refuse to go away and the Cubs know they will have to hold off the Brewers. They’ll get their chance early in the season’s second half, with a three-game set in Milwaukee July 28-30 and then a five-game series at Wrigley Field from Aug. 18-21.

As we shift gears into the final 66 games of the season, we attempt to answer the five more important questions surrounding this Cubs team:

1. Who will the Cubs trade for?

It’s difficult to nail down the exact names at this point, especially with two weeks remaining until the July 31 trade deadline. Several teams are hovering on the bubble that could change the landscape at the deadline.

For example, the Arizona Diamondbacks are currently five-and-a-half games out of the final playoff spot in the NL. If they falter out of the break, do they become sellers and make pitchers like Zac Gallen and Merrill Kelly available?

As for the specific positions: Plan on at least one starting pitcher and maybe two. The Cubs are almost certainly going to be in the market for bullpen help — potentially even high-leverage or closing options. And then third base has emerged as a clear area to upgrade by the end of the month with rookie Matt Shaw’s continued struggles at the plate.

Let’s start with the rotation.

The Cubs are without Justin Steele for the rest of the year, veteran Jameson Taillon is expected to miss several more weeks with a calf strain and Javier Assad has yet to pitch this season due to an oblique strain.

That leaves Shota Imanaga, Matthew Boyd, Cade Horton and Colin Rea in the current rotation. But even within that group, there are question marks.

Imanaga and Boyd form a dynamic one-two punch when healthy. But Boyd has already thrown more innings this season than he did in 2023-24 combined, so will he hold up all the way through the end of the regular season and into October?

A similar question exists with Horton, who sits at 85.2 innings this season after tossing just 34.1 frames in 2024 due to injury. Realistically, he may only have another 40 or 50 more innings as the Cubs place an emphasis on the big picture with the 23-year-old rookie.

And then there’s Rea, who has been solid overall this season (3.91 ERA) but has also had periods of struggle — he had a 5.92 ERA in a nine-start stretch from May 6 through June 22.

The rotation is a pressing need and the Cubs will have to address it in a big way before the deadline. “Big” meaning either with multiple arms to build out depth or with a quality arm that would slot in toward the front of the rotation and line up for a postseason start.

Jed Hoyer’s front office could also follow the formula we’ve seen from them in recent years (Jose Quintana, Cole Hamels) where they trade for pitchers who are more than just rentals and under contract for multiple seasons. The Marlins have several arms (Sandy Alcantara, Edward Cabrera, Eury Perez) that are under team control beyond 2025 but it remains to be seen who will be made available and what the asking price will be.

With the bullpen, it’s starting to feel like 2016 all over again. That year, the Cubs had a closer on the team already performing well (Hector Rondon), but wound up trading for a game-changing x-factor in the bullpen (Aroldis Chapman). Could they do the same thing again even with Daniel Palencia enjoying a breakout season?

When it comes to third base, it’s hard to gauge who may be available. A couple weeks ago, there was speculation that Alex Bregman may be on the market, but the Red Sox have been one of the hottest teams in baseball since then and currently hold a playoff spot in the AL. Eugenio Suarez could wind up being moved, but that goes back to whether or not the Diamondbacks end up as sellers.

At the very least, expect the Cubs to be in the market for a player who can factor in at third base part of the time.

2. How do the Cubs address roster questions in the short-term?

Given the nature of the trade market and the lack of surefire sellers right now, the expectation is most moves will come closer to the July 31 deadline. Which means the Cubs still have two weeks’ worth of games to solve for current roster issues.

The rotation is the most pressing need, and the Cubs have utilized an opener or veteran swingman Chris Flexen in Taillon’s spot. They may continue to roll with that plan, as they have off-days on July 24 and 31 to help alleviate some of the load on the bullpen.

Flexen, 31, has been one of the team’s biggest surprises this season as a minor-league signing who has flourished in the bullpen — 5-1, 1.47 ERA in 18 games (one start). He has rotation experience, including 30 starts with the White Sox last year, so he could handle a starting assignment in the interim.

As for third base, the Cubs seem to already be moving on from Shaw. The rookie started just one of the team’s final five games before the All-Star break.

Shaw has played strong defense at the hot corner, but is hitting just .198/276/.280 (.556 OPS) on the season. He’s still only 23, so hope remains for the future. But this year, the Cubs need more production out of third base and they’ve turned to veterans Jon Berti and Vidal Bruján.

Whether that continues or not coming out of the break remains to be seen, but either way, the Cubs see a clear weakness on the roster that can be improved at the deadline.

3. Will the bullpen hold up?

The most surprising area of the team this season has undoubtedly been the bullpen. The Cubs have endured struggles and injuries to some key members, piecing together a unit full of under-the-radar arms.

Daniel Palencia, Flexen and Drew Pomeranz were not even part of the Opening Day bullpen, yet they’ve been essential to the group’s success. Palencia has emerged as the closer with Ryan Pressly’s struggles and Porter Hodge’s injuries. Caleb Thielbar and Brad Keller were unheralded signings in the offseason and they’ve emerged as valued high-leverage relievers.

Put it all together and the Cubs have compiled the sixth-best bullpen ERA in baseball (3.54).

But here is the potential issue: Cubs relievers have the fourth-lowest strikeout rate in the league (20%). That could be a problem in the postseason, when the ability to miss bats is amplified.

Ben Brown might be a solution there. The 25-year-old struggled in the rotation and the Cubs sent him down to Triple-A Iowa to manage his innings. He does have experience as a reliever and has racked up the whiffs, with 35 strikeouts in 25 innings (12.6 K/9).

Bullpens are also volatile and the Cubs have one of the oldest groups in the league. They’ve been fantastic this year, but will they hold up down the stretch? Palencia and Ethan Roberts are the only relievers in the current group younger than 30 and the Cubs have four bullpen arms (Pressly, Pomeranz, Thielbar, Ryan Brasier) who are all 36 or older.

As we discussed already, the Cubs will be focused on augmenting the pitching staff — and possibly the bullpen — at the trade deadline. That will be one help. Other internal options could help if Brown and Hodge (currently on the IL with a shoulder issue) can get back on track in the big leagues.

4. What happens in the leadoff spot?

Ian Happ was the unquestioned leadoff hitter in this lineup all season — up until the week before the All-Star break, that is.

Manager Craig Counsell opted to bump Happ down in the order and go with a platoon atop the lineup — Nico Hoerner against left-handers and Michael Busch against righties.

Will that continue?

It very well might.

Busch never led off in his career until Sunday in New York and promptly homered in his first plate appearance. It would make sense to lead him off, as he is hitting .308 with a .394 on-base percentage against righties this season.

Hoerner has plenty of experience leading off (144 games) and he is raking against southpaws this season — .353 average, .378 on-base percentage.

Meanwhile, Happ has been in a funk at the plate. In the 14 games leading up to the All-Star break, the veteran left fielder hit just .111 with a .368 OPS.

If the Cubs want to maximize their lineup and get the best hitters the most at-bats, expect them to continue with the Busch-Hoerner platoon atop the batting order.

5. Will they hold off the Brewers and win the division?

This is the biggest — and most important — question surrounding Counsell’s group heading into the post-All-Star-Break schedule.

It’s what it all boils down to. Every question above this is ultimately about whether the Cubs can get where they want to go — the postseason. And the best path to the playoffs remains a division title.

Despite the close race in the NL Central at the moment, there is plenty of reason for optimism on the Cubs’ end. They have already shown a willingness to add key pieces at the trade deadline recently and they have an even stronger case to do so this year with the team’s strong start.

This is the Cubs’ window. Nobody knows whether Kyle Tucker will re-sign in the offseason or how the roster will look next year. But right now — this year — the Cubs are a legitimate World Series contender and Hoyer’s front office will be aggressive in that pursuit.

They have the means to acquire talent at the deadline as well, with a strong farm system that includes prospects like Owen Caissie and Jaxon Wiggins.

Plus, the Cubs have the third-easiest remaining schedule in MLB, while the Brewers have the fifth-hardest.

It is all lining up to what should be a fun fall around Wrigleyville.