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In case you missed it, Roki Sasaki is headed to the Los Angeles Dodgers. This news came out just a few days after it was reported that the Cubs were not on the final list of contenders for the Japanese ace. As a Cubs fan, or even just as a baseball fan, this stings. And it should. The rich get richer, and this time, the Dodgers didn’t even have to hand out a historic contract in order to get there. Consider that an insult, added to our injury.
For those unfamiliar, because Sasaki was posted to MLB prior to his 25th birthday, he was considered an international amateur free agent, meaning he will make the rookie salary for 2025 and be under team control for six seasons. He will receive a $6.5 million signing bonus. However, just about any other team could have, and probably would have, matched that signing bonus.
Basically, his decision had nothing to do with money, and everything to do with, well, everything else. Sasaki going to the Dodgers felt like a fait accompli as soon as it was reported that he would be posted.
Episode 2272 of the fantastic podcast Effectively Wild did a good job stating some of the reasons why. In the episode, hosts Ben Lindbergh and Meg Rowley were discussing Sasaki going to the Dodgers, and Rowley articulated something that I had been pondering, so I’ll quote her here:
“It goes to show that money can help to secure talent, but it doesn’t just end with the individual player that it helps you sign. It creates an understanding of your want as an organization. What do [the Dodgers] want? They want to go win a World Series. Again. They are not satisfied with one.”
In addition to the fantastic players (like Freddie Freeman, Yoshinobu Yamamoto, and Shohei Ohtani) whom you typically get to roster by spending big in free agency, you also signal to everyone else that you’re serious about contending for the World Series every single season. The fact of the matter is that the Cubs have not been signaling this of late.
Following a 2020 season in which they won the NL Central, the Cubs trimmed payroll by non-tendering fan favorite Kyle Schwarber and trading Yu Darvish. They went from third in payroll, to 14th, according to Spotrac. Team performance, unsurprisingly, also suffered. The team has not been back in the playoffs since. The payroll didn’t bounce back up into the top 10 until this past season, but currently, the Cubs sit 12th in projected 2025 payroll.
The Dodgers, on the other hand, have consistently invested resources to maintain a very good baseball team. Following a World Series in 2020, they signed Cy Young winner Trevor Bauer to try and fortify their rotation. That, of course, didn’t work out, but that was no sweat for them (at least from a baseball perspective). They traded for Max Scherzer and Trea Turner at the 2021 trade deadline, then (following a disappointing showing in the playoffs) signed Freeman that offseason.
Last offseason, of course, they brought in Ohtani, Yamamoto, Tyle Glasnow, and others, and they have maintained a similar level of aggressiveness this offseason, despite now coming off of two World Series championships in the past five seasons. They signed Blake Snell and Michael Conforto. They brought back Teoscar Hernández. They were serious players for Juan Soto.
The Cubs, meanwhile, did not even engage the superstar right fielder, and seem continually content to play in the middle tier of free agents. They’ve opted for guys like Marcus Stroman instead of Kevin Gausman. Dansby Swanson instead of Trea Turner. Jameson Taillon instead of Kodai Senga. Shota Imanaga instead of Yoshinobu Yamamoto. Some of those have worked out for the Cubs, but I’d argue the other options still offer a higher ceiling. Also consider for one second what the consistent, year-in and year-out yearning for value contracts from a big-market team communicates to players and agents: that you’re willing to win, but not at the expense of giving a player what you deem to be too expensive of a contract.
This doesn’t even touch on the developmental gap between the Dodgers and the Cubs. Our own Matthew Trueblood recently touched on the necessity for the Cubs to get everything possible out of their players at the major league level. Recall Ryan Brasier, Anthony Banda, and Evan Phillips. None were drafted by the Dodgers, and all were acquired for basically nothing. They combined to pitch 23 ⅔ innings in the playoffs this past season (over 16 percent of the total innings that the Dodgers played in), and did so to the tune of a 2.28 ERA.
Last offseason, the Cubs landed Michael Busch from the Dodgers in exchange for Jackson Ferris and Zyhir Hope. Both Ferris and Hope have seen their prospect status explode since entering the Dodgers organization. I am not here to relitigate that trade. The Cubs acquired someone to fill a position of need, and Busch had a very good rookie season for them. With that said, Ferris had some terrifying quotes about the difference in coaching between the two organizations.
“I just feel like coaching is a big thing. You wouldn’t expect coaching to be too different in the minor leagues or big leagues with teams, but it is a big difference," Ferris said. "When I first got traded over to the Dodgers, just kind of critique and fine-tuning little things with my mechanics even when I was younger. Which the Cubs didn’t want to mess with, since I was young. Now that we got to fine-tune some of those things, it really let me take off throughout the year.”
While he stops short of completely calling out the Cubs, I don’t think it takes much to read between the lines there: a former Cubs prospect feels he is getting much better coaching in his new organization. That is concerning.
On paper, it feels like the Cubs were a decent fit for Sasaki. They play in a big market. They currently employ Imanaga and Seiya Suzuki, two notable Japanese players. They would have employed him for very cheap, which is right up their alley. You know they were all-in.
Unfortunately, with contract offers all being equal, why wouldn’t a player want to play for an organization that has shown that it takes winning seriously, and is willing to continually invest resources to ensure a winning product is on the field? An organization that always seems to get the most out of all of their players?
I’d certainly pick the Dodgers. Wouldn’t you?







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