Chasing October, Not Hollywood

Chasing October, Not Hollywood

Tatsuya Imai said he wanted to beat the Los Angeles Dodgers after being posted at the start of the offseason, and now he’s got his chance — but there’s a pretty significant asterisk attached to that whole plan, at least for now. The 27-year-old Japanese ace just inked a three-year, $54 million deal with the Houston Astros, making a bold statement about where his priorities lie in his hunt for MLB success. The problem? At least for the next two years during, he’s going to have an awfully hard time actually fulfilling that goal during the regular season, assuming no lockout disrupts the 2027 season or beyond.

Imai was crystal clear about his ambitions when he was first posted by the Saitama Seibu Lions back in November. While plenty of guys might dream about joining the loaded Los Angeles Dodgers roster — where Shohei Ohtani, Yoshinobu Yamamoto, and Roki Sasaki are all holding down the fort as Japanese superstars living the California dream — Imai went a different direction entirely. According to CHOSUNBIZ in an interview with Japanese media, he explained exactly what he was thinking: I want to take them down. While I think it would be fun to play with them, winning against a team like that and becoming a world champion would be the most valuable thing in my life. If anything, I’d rather take them down.

That’s a hell of a statement. That’s the kind of thing that gets baseball fans talking, and it immediately set Imai apart from the typical wave of Japanese pitchers coming over to MLB. He wasn’t chasing the biggest contract or the most glamorous city. He wanted the smoke.

So what did he do? He signed with the Astros, which might just be the most poetic possible outcome given the history between Houston and Los Angeles. These teams don’t just have a rivalry — they have legitimate, unresolved beef. The Astros won the 2017 World Series, but that championship came with an asterisk that’ll probably never be erased thanks to the sign-stealing scandal. The Dodgers were furious. The animosity never really died down, it just got passed down and occasionally resurfaces whenever these teams face off.

Now here’s the thing about Imai’s dream to beat the Dodgers: It’s not happening in 2026, and it probably won’t happen the year after either. The Astros and Dodgers don’t meet in the playoffs every season, and depending on how the next two seasons shake out, Imai might end up looking at an opt-out opportunity after each of those years. If he decides to stick around through his entire contract, he may not get a real crack at taking down the Dodgers in a meaningful playoff situation until 2028 at the earliest. That’s assuming no labor stoppage after the 2026 season. The player opt-outs in his deal suggest that Imai is already thinking ahead, planning his next move after these first couple of seasons, which means this whole I’m going to beat the Dodgers narrative might get sidetracked pretty quickly.

But here’s what’s really interesting about this whole situation: The Cubs couldn’t be bothered to try. Not seriously, anyway.

The Cubs were indeed in the mix for Imai, just like they were supposedly in the hunt for Dylan Cease at the end of November before the Winter Meetings. But when it came time to actually write the check, the Cubs organization did what they’ve been doing a lot lately — they backed away. They weren’t willing to meet Imai’s terms, which, by the way, ended up being a relatively modest $54 million over three years. The deal included significant opt-outs and incentives, making it even more practical for teams willing to take a calculated risk on a young ace trying to prove himself in a new league.

The Cubs didn’t budge. And that’s where the real story of cheapskating emerges.

This team was already on thin ice with their fanbase after they refused to match what Toronto was willing to offer Dylan Cease. The Blue Jays went all-in with a seven-year, $210 million deal  that demonstrated real commitment to building a contender. The Cubs? They exited the Cease negotiations once things climbed toward the $200 million range. More frustratingly, the Cubs continued their stubborn refusal to use deferred money in contract negotiations, a practice that could have made a massive difference in their ability to acquire top talent without exploding their luxury tax payroll.

So when you string these two failures together — Cease getting away to Toronto, and now Imai heading to Houston — it paints a picture of a franchise that’s more interested in maintaining fiscal discipline than actually trying to win. The Ricketts family owns the Cubs, and their ownership group has shown for years now that they’re not willing to deploy the kind of financial firepower that championship contenders require.

Here’s the thing, folks: Imai will get his chance to test himself against the Dodgers eventually, assuming he stays healthy and continues dominating in MLB. But for the next two years, he’ll be doing it in Astros colors, chasing a World Series ring while the Cubs sit on the sidelines, unable or unwilling to make the moves necessary to stay relevant in a competitive division. It’s a fitting representation of where this franchise stands heading into 2026 — plenty of young talent, some interesting pieces, but a front office that seems more committed to penny-pinching than payoff.

With that… Imai’s quest to bring down the Dodgers is just beginning. The Cubs’ window to be part of that story? That ship sailed before talks actually began.

If you cannot play with them, then root for them!

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