The Cubs are actually good! So what should they do at the trade deadline?

The Chicago Cubs have exceeded preseason expectations so far in 2021. Entering Monday’s series opener against the San Diego Padres (10 p.m. ET on ESPN), the Cubs are now seven games over .500 at 33-26 and in a tight battle with the Milwaukee Brewers and St. Louis Cardinals for the National League Central lead.

Chicago also has several upcoming free agents on their current 26-man roster with stars including Kris Bryant, Javier Baez, Anthony Rizzo and Craig Kimbrel set to hit the market after the season. This is the same team that traded Yu Darvish in the offseason of what general manager Jed Hoyer labeled a transition phase for the franchise.

So what should the Cubs do as the trade market starts to take shape before next month’s deadline? Is this a team that can win enough to make a championship push? Or would it be better off looking to retool? And are the Cubs good enough to keep winning if they stand pat? We asked ESPN MLB experts Jeff Passan, Jesse Rogers and David Schoenfield to weigh in on the crucial next few months on the North Side of Chicago.

The Cubs are seven games over .500 and in first place, so what should they do at the trade deadline if they keep this up?

Rogers: There won’t be any choice but to add. Wrigley Field is about to be packed for the next 3½ months, and you don’t trade away talent when you’re in first place. In reality, being near the top of the standings is no shock, only how they’ve gotten there, because even after trading Yu Darvish, the Cubs had plenty of talent. It helps to reside in a mediocre division. So yes, augmenting the roster would be in order. The only question is how far will Jed Hoyer go? Will he empty the farm for a couple of rentals? Doubtful. So it could be additions around the edges. And the bigger question is what if the Cubs are three to five games out of first place come late July? Then the decision becomes much tougher. Focusing on the future would be more likely.

Passan: Be judicious. Because here’s the reality: As well as the Cubs have played, as much as they’ve exceeded expectations, they also are run by pragmatists. And anyone who is looking at this roster and comparing it to the Los Angeles Dodgers’ and the San Diego Padres’ — and to a lesser extent, the San Francisco Giants’, the New York Mets’, the Atlanta Braves’ and even the Milwaukee Brewers’ — understands that a World Series run remains a long shot regardless of how well the Cubs have played.

That’s the calculus this time of year. The Cubs were willing to give up a prospect of Gleyber Torres’ caliber to acquire Aroldis Chapman because they were the best team in baseball in 2016 and had one glaring weakness. Not only does this Cubs team have far more weaknesses — its outfield hasn’t hit (aside from Ian Happ in May), and its starters’ ERA of 4.62 is 21st in baseball — perhaps its greatest strength thus far this season, its bullpen, is due for regression.

So, yes, if they’re in contention to win the NL Central, they should add talent. But it might be smarter to hunt for bargains.

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Schoenfield: I think back to when Jed Hoyer took over from Theo Epstein as president of baseball operations in late November and in Hoyer’s initial Zoom call with reporters said, “In this job, you always have one eye on the present and one eye on the future. I think that eye might be a little bit more focused towards the future than usual, but that doesn’t take away from the goal. The goal is always to make the playoffs and give this organization a chance to go deep in October.”

A month later, the Cubs traded Yu Darvish, and while the Cubs did eventually make some late signings on the free-agent market, the Darvish trade was a clear signal: The Cubs are not all-in on 2021. Of course, that dynamic can’t help but change if the Cubs remain in first place in late July, but that mostly means not trading Kris Bryant, who might be the second most desirable player on the trade market after Max Scherzer if he were available, given his great start. Now, what they should do is go after Scherzer to bolster the team’s biggest hole, but even if the Cubs wanted to do that, it seems unlikely they would be able to put together the best prospect package anyway. So, the likely scenario is a couple of fringe moves around the edges — a second-tier starter, maybe an outfielder depending on how the Cubs feel about Ian Happ and Jason Heyward.

Is it possible to compete this year and retool for the future at the same time?

Rogers: Absolutely. The best way to do that would be to trade closer Craig Kimbrel. That’s one guy out of 26 who impacts games every few days. It would be a loss, but righty Ryan Tepera was just named reliever of the month in May; perhaps he could step up for a two-month run as closer. Either way, Kimbrel could bring back a few good prospects while the Cubs continue on their winning ways. Competing doesn’t necessarily mean winning it all. The Cubs could definitely do both — even if they trade more than just Kimbrel.

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Passan: Of course. That’s exactly what they’ve done, in fact. It’s easy for Cubs fans right now to lament the deal that sent Yu Darvish to the Padres, but the team’s farm system was an absolute mess, and adding four prospects under 21 years old — including Reggie Preciado and Owen Caissie, two very talented bats — was the sort of deal that teams balancing today with tomorrow make. Tampa Bay and Oakland are two teams that have mastered the look-at-the-future-but-still-win-now needle-threading, and while it’s difficult, it’s certainly possible.

Schoenfield: I like Jesse’s idea of trading Kimbrel, who suddenly looks like vintage Kimbrel from a few years after two miserable seasons during his first two years with the Cubs. His $16 million option for 2022 doesn’t even look that bad right now, and it comes with a $1 million buyout, so he’s attractive to any team in need of a closer; the Braves, Phillies, A’s and Astros are possible destinations. Is there a scenario where the Cubs trade Bryant for a couple of cost-controlled major leaguers? I suppose it’s possible, but how many teams are willing to trade young, major league talent for a two-month rental? Seems unlikely, although — just thinking out loud here — maybe a team like the Mets would be willing to trade Dominic Smith, who could replace Anthony Rizzo at first base next season (and play left field the rest of 2021, with Joc Pederson sliding over to right).

Will the Cubs make the playoffs this year?

Rogers: It’s going to be close, but I’ll say no. Milwaukee hasn’t found its stride yet even though it is neck and neck with the Cubs right now. The Brewers are likely to pass them in the standings in June — a hectic and tough month for Chicago. And here’s a factor no one is considering: Some of the Cubs’ best pitchers are young and hardly played in 2020. They’re either going to hit a wall or the team is going to back off them — something the Cubs already stated is a possibility. Standout starter Adbert Alzolay is at the top of that list. The Brewers aren’t backing off Brandon Woodruff or Corbin Burnes or Freddy Peralta or Josh Hader. If the Cubs had last year’s pitching staff with this year’s offense, they’d be set, but there are too many variables in 2021. The wild card does remain a possibility, though it’s looking more and more like three teams from the NL West could make the postseason. It’s still way early to really know though.

Passan: I went with the Brewers to win the division before the season. I want to stick with them. I also look at their .211/.297/.371 team triple-slash and wonder in what universe a team that cannot hit wins a division. And the answer, I believe, is one where sportwide the line is .236/.312/.396. As long as they can keep Brandon Woodruff, Corbin Burnes and Freddy Peralta healthy, the Central is the Brewers’ to lose, though the Cubs are good enough to remain competitive and have a healthy shot at stealing the division. As for the wild card: Atlanta has surged to the point where seeing the East potentially steal a slot isn’t entirely far-fetched, but the two are the West’s to lose.

Schoenfield: The Brewers were my preseason pick, as well, and certainly the performance of that trio at the top of the rotation is only further reason to lean in there. But they can’t hit, especially if Christian Yelich continues to have issues powering the ball over the fence. I do believe Kyle Hendricks and Zach Davies will be better moving forward, although tempered by some bullpen regression, and if the Giants fade in the NL West, the second wild card could come from the NL Central. Bottom line: I’ll stick with the Brewers to win the division, and since the Giants’ pitching looks pretty legit, they win a wild card alongside the Dodgers or Padres.

If the Cubs do make the playoffs, can they compete with teams like the Dodgers and Padres or is their success a product of a weak NL Central?

Rogers: Despite dominating those teams so far in the regular season — all at home — the Cubs don’t have the rotation to compete for a World Series run. The fact that this is even a question is a testament to manager David Ross and the job the whole organization has done to this point. This was supposed to be a transition year. Jed Hoyer said those exact words in spring training. So, there’s no shame in saying they are maxing out right now, but it’s hard to see them navigating through the top teams in the NL in October. They would need two top starters to change my mind. Again, this discussion wasn’t even on the table in March, so kudos to them for making us talk about it!

A new name has emerged as a possible No. 1 overall pick. Whom else could your favorite team be targeting when draft day arrives?

Kiley McDaniel

Passan: Yes. Yes, they can compete. Yes, their success is a product of a weak NL Central. The biggest advantages teams like the Dodgers and Padres hold over the Cubs is with starting pitching. But remember: The postseason has evolved into a bullpen-centric month, and here are the Cubs relievers’ ranks in baseball: ERA (2nd, 2.72); K/9 (first, 11.18); HR/9 (fourth, 0.75); strand rate (third, 80.5%); groundball rate (2nd, 49.4%). Get a starter through the lineup twice — or perhaps even fewer times — and let David Ross maneuver with the pen. It’s been a winning formula thus far, and with the stuff some of the Cubs’ relievers have, they certainly could replicate it in October.

Schoenfield: It’s not like the Dodgers or Padres look unbeatable right now, and I’d almost rather face them in a best-of-five series than Jacob deGrom and the Mets. Any chance for the Cubs would have to rely on some heavy bullpen work, but that’s a tough way to get through an entire postseason. Scherzer would help their odds, but I’m not sure there’s another difference-making starting pitcher out there who would lead one to think the Cubs could beat the Dodgers or Padres.

If they decide to go for it in acquiring talent, what should the Cubs target at the deadline?

Rogers: Starting pitching. Max Scherzer would fit nicely. Or Dylan Bundy. Or maybe the Cubs determine one of the Rockies’ starters would flourish outside of Coors Field. The Cubs don’t have to be too picky if they’re going for it. Top and/or middle-of-the-rotation guys are essential for an October run. Standing pat would be a disaster, so it’s either unload in some capacity or go for it. But it’s hard to see the Cubs giving up a top prospect in any deal since going down that road in recent years helped deplete their farm system in the first place.

Passan: Jesse’s got that Prada taste, and while the Cubs do have the money to go out and get a Scherzer, doing so would cost Brennen Davis and more, and for an organization that understands the folly in going all-in today at the expense of tomorrow, the likelihood of that happening is slim. They would be better served to look at Kyle Gibson (back from the injured list and sporting a 2.06 ERA), Dylan Bundy, Andrew Heaney and perhaps Michael Pineda. No, those names aren’t sexy. Neither is the Central, and the goal right now is simply to win it. One bat worth keeping an eye on: Trey Mancini, who isn’t a free agent until after the 2022 season, wouldn’t cost a significant amount in prospect capital and can play right field and leave in the late innings with Jason Heyward taking over.

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Schoenfield: Scherzer is the big guy. It doesn’t hurt to ask the Rockies about German Marquez, but he would be expensive, since he is signed through 2024 and the Cubs aren’t emptying an already thin system. Marquez’s teammate Jon Gray is an option. Other free-agent pitchers on likely noncontenders include Alex Cobb, Andrew Heaney, Mike Minor, Danny Duffy, maybe J.A. Happ and Michael Pineda if the Twins don’t bounce back and Robbie Ray and Steven Matz on the Blue Jays.

How many of these players will still be Cubs on Aug. 1: Kris Bryant, Anthony Rizzo, Javier Baez and Craig Kimbrel?

Rogers: Three. Kimbrel will be gone, but the three position players will still be here. This scenario would keep them competitive in 2021 but still net them a good prospect or two.

Passan: Four. The Central is weak enough — and the Cubs just good enough — to warrant making a run. Though let’s not forget, Jed Hoyer was part of the Boston front office that dealt Nomar Garciaparra in 2004, so it’s not like he is above dealing a core player — especially one who’s about to hit free agency — with an eye on winning in the present and winning more in the future.

Schoenfield: I’ll say the Cubs are close enough that all four remain on the team with them ultimately deciding to keep Kimbrel and see if they can ride the bullpen into the postseason.