[COPY] - Chicago Cubs Trade Deadline Scenarios: Welcome to the Darkest Timeline

Welcome to the Darkest Timeline. We pessimists live in fear of the Darkest Timeline. This year, we may be seeing it play out in real time. The Cubs haven't won a series in a month. The infield is struggling at the plate, concerning for players over or near 30. Cade Horton is hurt. Justin Steele is (still) hurt.

If the Darkest Timeline persists, the Cubs may have to sell off some assets and do a reset. No, it's not a likely scenario. The Cubs project to be much better than this, and this is Jed Hoyer's Ode to the IVY Model. If there's any chance of a Wild Card berth, the Cubs will explore every avenue to achieve it. They were built to win this year. A selloff was not even supposed to be a passing thought.

What would spawn the Darkest Timeline into existence? As of this writing, the Cubs are 5-18 since their last 10-game win streak. If they repeat this and are 10-36 over a quarter of the season, the division is out of reach and they likely will be out of the Wild Card hunt. Given the 12 potential free agents on the roster, losing out on any prospect capital to lose them for nothing is an unlikely scenario. It probably won't—can't—get that bad, but what if they go 15-30 over the next six weeks? That would put them completely into sell mode by the end of July.

TRADE OPTION 1: MATTHEW BOYD
If he can return from his meniscus injury (as the team currently hopes will happen late next week) and pitch effectively, Boyd would be an attractive commodity for, well, every team. Last season, the veteran averaged six innings per start and pitched beyond that point seven times, reaching 180 innings for the season. Any team that looks to contend into October can use a reliable arm.

Boyd's trade value hinges on his health. He's only made five starts this year with a 6.00 ERA, has a current knee injury, and is not exactly a glowing beacon of durability. But teams will value an innings eater with playoff experience, especially on a contract they won't have to pay for next year. 

Boyd's contract ends this season and the team acquiring him would only be on the hook for part of his $14.5-million salary. Boyd would probably welcome a chance to pitch in meaningful games (remember, this is the Dark Timeline for the Cubs, not for everyone) to enhance his earning potential next offseason. Boyd would be the first domino to fall in a series of events.

TRADE OPTION 2: IAN HAPP/SEIYA SUZUKI
Yes, they have no-trade clauses, so the Dark Timeline has to account for that. This is the scenario that could lead either of these free agents-to-be to be dealt this summer:

The Cubs, seeing their foundation crumble and not wanting to extend older outfielders, inform Happ and Suzuki that Matt Shaw and Kevin Alcántara will be prioritized, and they will not get consistent playing time the rest of this season. The team also tells them that they have zero intention to bring them back for 2027. The two outfielders then decide to move on, play meaningful games, and hopefully increase the value of their free agency for 2027.

The Cubs, at this point, are short on arms in the minor leagues, as well as potential impact youngsters. Dealing Happ and Suzuki is almost akin to dealing Yu Darvish. They would need to get at least one legitimate prospect, much like the team received when they dealt Javier Báez to the Mets for Pete Crow-Armstrong. The idea would be to jump-start their flagging farm system.

Both players would have appeal to contenders seeking middle-of-the-order bats without long-term commitments. Teams who miss out on bigger deadline names could view either outfielder as an important addition for a playoff push.

TRADE OPTION 3: CALEB THIELBAR/JACOB WEBB/HOBY MILNER/ANY RELIEVER NOT NAMED PHIL MATON
Bullpen arms are always in high demand at the deadline, especially expiring contracts. All of these players listed can be free agents next season, lessening risk to the acquiring team. For the Cubs, dealing relievers can result in high-upside arms. (Where would the team be without Ben Brown, whom they got for David Robertson in 2022?) None of these relievers would cost much in salary, either, and they've all been quite successful in Chicago.

It would hurt to lose them for Jed Hoyer, but remember, this is the Dark Timeline, and they stink. So why keep aging relief pitchers on one-year contracts? The Dark Timeline dictates the Cubs disperse these valuable players to other teams, where their talents can be on a bigger October stage.

Would all of these be painful, especially for the architect, Hoyer? Absolutely. But if the Cubs eventually want another true contender, they can't skip steps. They have to extract maximum value from their current assets if the season goes sideways. 

For better or for worse, the Cubs are married to their core of Alex Bregman, Dansby Swanson, Nico Hoerner, and Pete Crow-Armstrong for at least four more seasons, and how they build around their strengths and weaknesses will dictate the team's success. If the Dark Timeline becomes the actual timeline, the Chicago Cubs would look much different in September, and fans will be looking down the barrel of another retool, if not a full rebuild. Even here, in a timeline the darkness of which we don't yet know, it's starting to feel like the pies are burning.