Cubs ‘Viable Contender’ for Rōki Sasaki, May Have Uphill Climb Based on Pitcher’s Preferences

The Cubs have already submitted an introductory presentation to Rōki Sasaki and Joel Wolfe, the high-profile agent at Wasserman who also reps Seiya Suzuki. That connection could work in their favor, as they were able to recruit Suzuki in the dead of winter after he’d just met with the Padres in San Diego. It could also work against them, and not just because Wolfe recently lamented the possibility of the (former) outfielder being moved to DH as trade rumors swirl.

I’m not talking about sour grapes, nor is this similar to how a college coach will recruit a new class with promises of being there for them even though he knows he’s about to take a bigger job next week. Even though Sahadev Sharma and Patrick Mooney reported that the Cubs are “viewed as a viable contender for the Japanese pitcher at this preliminary stage,” Wolfe’s description of his client’s personality and his possible preferences seems to put the Cubs and Chicago at a disadvantage.

“I think that there’s an argument to be made that a smaller, mid-market team might be more beneficial for him as a soft landing,” Wolfe told the media at the Winter Meetings earlier in the week. “Rōki is somewhat quiet. He has a dry sense of humor. He’s very witty. He’s not verbose. He doesn’t necessarily love people that are verbose.”

To add a little more context to this, Wolfe added that the Japanese media has been “very tough on (Sasaki)” and that “It’s affected him mentally, a little bit.” My first thought when I read this is of Randy Johnson being traded to the Yankees ahead of the 2005 season. It felt like a bad fit at the time for a quiet homebody type and Johnson had two mediocre-to-disappointing seasons in the Bronx before being traded back to Arizona to be closer to his family. A herniated disc certainly didn’t help his performance in 2006, but he seemed miserable from a distance.

Under normal circumstances, I’d be inclined to say Wolfe was simply engaging in a little gamesmanship to get the big-market clubs to essentially buy his client a little more peace of mind. But with Sasaki limited to a minor-league deal with a minimum salary and an international amateur bonus that can only get to around $12 million, this isn’t a situation in which money is paramount. Regardless of market size, I would imagine teams are going to have to, uh, pitch the pitcher on their ability to provide or foster a relatively insular community around him.

To that end, the Cubs have a wealth of experience recruiting Japanese players through the posting process and free agency. What’s more, this concept is just an extension of what Jed Hoyer said during his end-of-season press conference about creating an environment that puts players in better position to outperform their expectations. Rather than altering anything with their organizational culture just to fit one coveted player, the Cubs were already set on making changes and can now sell Sasaki on how that will help him.

Now they might just want to find a way to scrub social media so Wolfe can’t see the way Cubs fans treat guys like Suzuki and Ian Happ who don’t put up god-tier numbers. Even Kris Bryant, the best player the organization has seen in decades, was vilified following a dubious report about turning down an extension offer and his inability to rack up multiple MVP awards. Being limited to a league-minimum salary will take some of the heat off of Sasaki, but fans can be merciless.

That isn’t going to be any different in New York or Boston, and LA can be tough for the five innings a game that fans are actually at the ballpark. But when I think about what Wolfe has said during this process, I keep going back to clubs like the Rays or even the Twins. The Padres look like a serious contender as well because they can offer Sasaki gorgeous weather, a strong culture, and the ability to fade into the background more easily when he’s not pitching.

It feels like Sasaki wants the benefit of anonymity, which could actually be why he jumped to MLB early. Think about it: Landing a deal for $300+ million comes with huge expectations. A $10 million bonus and $800K per year? Not so much.

A lot of folks believe this is all a foregone conclusion and that the righty, like Shohei Ohtani last year, is simply going through the obligatory courtship process before ultimately signing with the Dodgers. That’s hard to dismiss given all the speculation from various outlets, but I maintain hope that the rich won’t get this much richer. Still, the Dodgers may have an advantage in that they boast so many stars that Sasaki can easily keep his head down and walk in their shadows to avoid the bright lights of Hollywood.

As much as I’d love for the Cubs to sign this guy, they strike me as being somewhere in the middle when it comes to appealing to Sasaki’s wants and needs. They aren’t a small market with a forgiving fanbase and docile media presence, nor do they have enough star power to draw attention away from him. What they do have is a front office that prizes value above nearly everything else and that will doggedly pursue good deals, so I’d imagine their presentations will be absolute no-skip bangers.

Sasaki will have to wait until after January 15 to get a maximum bonus as part of the 2025 international signing class, but he only has until January 23 to decide based on his 45-day posting window. That gives him plenty of time to research his options, provided he needs it. Now watch him sign with the Dodgers this weekend right at the close of the 2024 international free agency for whatever they’ve got left in their pool. That might be my Joker origin story.

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