When the Chicago Cubs signed Shota Imanaga, the top line of the deal was four years and $53 million. But the deal is about as creative as one could imagine.

No, it’s not Shohei Ohtani creative. But this offseason does represent a real fork in the road for Imanaga and the Cubs, a franchise the former Japanese star wanted to play for so much that he stealthily slipped into Chicago before Cubs Con in 2023 to get a feel for the city before he signed the deal.

Now? He could end up being a rich man or a free agent. It isn’t just about the money. It’s about Imanaga’s future and whether he’s a fit for the Cubs for what could be the next three years. Chicago won’t have much time to make that decision after the World Series, either.

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As presented by Jordan Bastian at MLB.com, the easiest thing the Cubs could do would be to trigger a club option to keep the left-hander. But it isn’t an ordinary option. Most contract options are year-to-year. This option, as written into the deal, is a three-year option. If Chicago triggers it, then it’s tied to Imanaga for three more seasons at a cost of $57.75 million.

That means the Cubs are comfortable with tying themselves to the 32-year-old for three more years. On paper, that works. He is 24-11 with a 3.28 ERA in 54 starts since he joined Chicago in 2023. But he’s spent time on the injured list both seasons, and he’ll be 35 at the end of the deal. The Cubs may not be comfortable with the money and his age.

If the Cubs aren’t comfortable, perhaps Imanaga is? By declining the option, the Cubs then put the lefty’s future in his hands. He would then have a one-year option that is worth $15.25 million. If Imanaga wants to stay at that cost, he can do so.

But it also triggers a different option for the Cubs. After the 2026 season, the three-year option would become a two-year option for Chicago, and the process would repeat.

That might be a good middle ground for the Cubs. But Imanaga may feel he’s worth more on the open market. Plus, by entering the market he would compete with San Diego’s Michael King, Houston’s Framber Valdez and San Diego’s Dylan Cease for the top free agent starting pitcher on the market.

The final option is both sides declining the option. In that case, the Cubs do have one final arrow in the quiver — the qualifying offer. Teams are allowed to make a qualifying offer to impending free agents. This year the QO is an estimated $22 million. Imanaga can take the money or turn it down. But, if another team signs Imanaga, then Chicago gets draft pick compensation.

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Right now, Chicago has Matthew Boyd, Jameson Taillon, Cade Horton and Javier Assad under contract. That is four-fifths of a starting rotation. Imanaga would complete it before the Cubs even hit free agency.

But that’s the question. Do the Cubs want Imanaga? Does Imanaga want the Cubs if they don’t trigger the option? Soon, the Cubs will have to figure that out.

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