Ranking the Cubs' Contract Option Decisions, from Easiest to Toughest

Image courtesy of Geoff Burke-Imagn Images

Cubs Video

The most important decision that will be made about a Cubs player's contract option for 2027 won't be made by the Cubs. Clay Holmes, whom the team acquired on August 3 from the Mets, can elect to receive a $12-million salary next season, or to hit free agency for the second time. The Cubs have no say in the matter, and Holmes is overwhelmingly likely to decline his option. In fact, if he accepts it, that will feel like a red flag about his health or his hopes for next year.

The team also holds three club options, though, and there are four more deals that include mutual options for next year. Mutual options are as much financial tricks as real contract years, because both sides must exercise them in order for the option to be activated. That hardly ever happens, and (spoiler) it won't happen with any of these deals, either. To run through them in an organized way, let's rank these options in terms of the difficulty of the Cubs' decision about them, from easiest to most difficult.

1. Matthew Boyd

Boyd's contract paid him $10 million in 2025 and $17 million in 2026, including his signing bonus. The 2027 option attached to the end of it is worth $15 million, but it's only a $13-million decision for the team. If either side declines the option, Boyd receives a $2-million buyout. Even at $15 million, a one-year commitment to Boyd is a no-brainer. At $13 million, he'd be a steal. All of that means that he'll turn down his half of the option and become a free agent, but from the Cubs' side, exercising it should take almost no thought at all.

2. Carson Kelly

This is the same thing, at the other end of the battery. Kelly's contract paid him $5 million each of the last two years, but he'd make $7.5 million in 2027 if the mutual option were exercised. There's a $1.5-million buyout in this one, so the difference for the Cubs is only $6 million. As with Boyd, this is an easy call. Kelly is an aging catcher, but he's worth at least $6 million per year on a two-year deal. For one season, that price would be a colossal bargain. The Cubs won't be so lucky; Kelly will become a free agent.

3. Caleb Thielbar

These aren't all clear-cut in the same direction. Unfortunately, Thielbar looks to have reached the end of his improbably great career. He's nearly 40 years old, and there were too many days this season when it looked like it. His stuff isn't entirely gone, but it's become inconsistent and unreliable. A mutual option in the deal the Cubs and Thielbar signed last winter would pay him $6 million for 2027; he's not worth that money. The Cubs will turn down their half of the option and pay Thielbar $500,000 as a buyout. Then, they'll have to find other relief options.

4. Javier Assad

Declining Assad's option is also relatively easy, but the reason is purely logistical. When the team and the player avoided arbitration last offseason, the Cubs negotiated a $3.3-million club option for 2027. They'll turn that down, but Assad won't become a free agent, as a result; he'll just be dumped back into the arbitration system. He's not in position to garner a big raise from the $1.8 million he made in 2026, because (thanks to repeatedly being optioned to the minors) he didn't get to a new service-time threshold. He earned too little service time to go from a 3+ to a 4+ guy, so he's still three years from free agency. The system is being deeply unfair to Assad. He'll turn 30 next July, and he's pitched 425 innings in the majors over parts of five seasons. Yet, he won't be a free agent until at least the end of the 2029 season, unless the Cubs non-tender him between now and then. That's unlikely to happen this winter. For one more year, he's an optionable swingman. He'll probably make about $2.3 million along the way, instead of the $3.3 million he'd receive if the Cubs exercised their option.

5. Jacob Webb

We're still in the realm of the relatively easy. Webb's one-year contract for 2026 contains a club option for 2027, worth $2.5 million. Even after Webb had a brutal finish to the year, he's clearly worth that much. Assuming the Cubs are more successful in reinforcing their bullpen next season, Webb should slide back into a middle-relief role. As that kind of guy, rather than a de facto relief ace, he's well worth keeping around. He was a positive presence in the clubhouse, too, which makes the decision easier on roster spots like this one.

6. Hunter Harvey

Yes, believe it or not, there's something to think about here. Harvey barely pitched in 2026, with trouble in both his triceps and his shoulder. He's due $8 million if both sides exercise the mutual option for 2027, with a $1-million buyout if either side declines it. Presumably, Harvey will trigger his side of the option. He's not in a position to make more than that on the open market. Before the Cubs decline their half, though, they have to consider upside. Harvey does have the kind of arm the team has needed more of for several years. When healthy, he throws harder and strikes out more batters than almost anyone else in the Cubs organization. His health is so unreliable that the team should still turn down the option, unless they intend to spend huge money this winter to address their pitching shortfalls. If they do plan to get as ambitious as they should, though, they might be right to roll the dice on Harvey for $7 million in net spending.

7. Colin Rea

There's no question that this is the toughest call. It's a club option, so if the Cubs want Rea back in 2027, he'll be back. For that to happen, they have to be willing to pay him $7.5 million. That's the salary on his option. Even if they turn that option down, they'll owe Rea $1 million, so it's a $6.5-million decision. At that number, he's pretty fairly priced. He's a great organizational soldier, willing and able to pitch in multiple roles. He's been durable and resilient, and his career (like Thielbar's) has stretched longer and been more fruitful than anyone would have expected half a decade ago. He's not clearly worth $6.5 million, but nor would he clearly impede the team's roster-building at that salary. Keeping him around makes sense. However, the team might decide that they need the roster spot and the extra scratch more than what Rea brings to the table.