The Cubs decided to position themselves as late sellers at the MLB trade deadline. Still, these players are coming up on their final days.

The Chicago Cubs at one point looked like one of the most obvious sellers in regards to the MLB trade deadline. After all, Chicago had players on contracts set to expire that were performing well while the rest of the team around those disparate pieces failed to click.

Then, almost suddenly, it all started to work. Chicago won as many as eight straight leading up to the trade deadline and convinced management they should be buyers, not sellers.

As such, the strategy changed dramatically, and pieces that were almost sure things to be on the move ended up staying in Chicago for the postseason push. Some of them won't be long for the North Side, though.

Expect to see these Cubs, who weren't traded, gone from the team before next season starts.

Cubs need to cut losses on Jameson Taillon

Jameson Taillon, one of the marquee signings of free agency for the Cubs, has not panned out how Chicago had hoped at all. Following a triumphant few years where Taillon revitalized his career reputation and trajectory, he cashed in with a multi-year contract worth $68 million. The Cubs look like they got a lemon so far this season with Taillon currently holding a 5.36 ERA (85 ERA+) and 1.394 WHIP. And this is just year one.

The good news is that Taillon is improving as the year goes on with two earned runs or fewer in four of his last five starts. His ERA, which peaked at 8.2 on May 20, has fallen to 5.36 as of Saturday.

I'm skeptical of the results, though, with him giving up exactly seven hits in three of those five instances. He's proven the ability to work out of trouble, but his FIP (field independent pitching) is still above 4.5, the third-worst among Cubs qualifying pitchers. But if his progress continues, Chicago should leverage that by stoking some trade interest in the struggling player ready to come around.

Simply put, I think Taillon is improving enough to get some bites in the offseason trade market, and though the return may not be what Chicago wants for a pitcher once thought to be a game-changer, they should go ahead and sell to get themselves out of the contract (both in length and financially) to earn themselves the flexibility to spend elsewhere.

Taillon's contract goes through 2026 and increases in value up to $18 million for the final three years. Getting out of this one would be a big help to the flexibility the front office has in its decision making.

Cody Bellinger might want to stay at Wrigley, but has earned himself a big new contract

Cody Bellinger has hinted that he would be open to staying with the Cubs on a new contract. The star outfielder and former MVP who looked completely broken before 2023 has completely revitalized his reputation this season with Chicago. After signing a one-year contract, he will command a hefty price tag in free agency on his next deal.

I suspect Bellinger probably won't want to take much of a discount on what could be his last multi-year lucrative deal of his career. The Cubs will get outbid for Bellinger.

There were certainly opportunities to try to sell high on Bellinger as a trade deadline rental. Plenty of teams — the Yankees perhaps most notable — were looking for an outfielder with a bat, and Bellinger's versatility as a DH, outfielder, and first-baseman made him plenty attractive.

The Cubs were winning, though, and decided to be buyers rather than sellers. Nothing wrong with that, as fans at Wrigley would rather see the team get serious about winning than sell off smart contracts at the first chance they get.

Bellinger will want to stay in Chicago, and Chicago will want to keep him. The team just won't have the money to match the sizable offers he'll get in free agency.

Marcus Stroman will leave Cubs for a fair deal elsewhere

This narrative, all season long, has been complicated.

On one hand, Marcus Stroman has been a Cy Young candidate and outwardly appears deserving of a contract extension, especially when he clearly wants to be in Chicago and might take a below-market deal to stay for the next few seasons.

On the other hand, Stroman is 32 years old and potentially pitching the last elite season of his career. Chicago, already with some questionable contracts on its books, including the aforementioned Taillon in the starting rotation, may not be wise to hitch its cart to an aging pitcher on a lucrative multi-year deal.

There's plenty of nuance here, but one thing is clear: Stroman will get paid. He technically has one more year on his deal but has a player opt-out after this season that he would be wise to exercise. With a league-leading 0.6 hits per nine innings and a second-best-in-majors ground ball rate, there's lots to love about Stroman who has put forth a 3.85 ERA and 15 quality starts (tied for third in MLB).

Stroman, similar to Bellinger, will get offers elsewhere that the Cubs just can't reasonably match.

While Stroman appears more likely to give Chicago a discount than Bellinger, I think he may sour on the organization after they failed to engage with him on a midseason contract extension despite his very public pleas to get something worked out.

One wrinkle, here, though… If the Cubs can get out of some money (such as by trading Taillon, for instance) I could see them committing it to Bellinger or Stroman.