It's important to start with this context before diving into the industrywide reviews of the Boston Red Sox signing Masataka Yoshida, a free agent outfielder from Japan who received a five-year, $90 million contract from the Red Sox:
Baseball is hard.
The act of playing baseball is notoriously difficult, as is predicting the future of it. Projecting players in Triple-A simply going up one level to the big leagues is much harder than you might think. Projecting players who have starred in a professional league across the globe? Well, that is even harder.
Yoshida didn't appear in my free agency rankings going into the winter as most execs I spoke with didn't think any foreign players other than Kodai Senga were likely to hit the market and be good enough to make the top 50. It became clear in the following weeks that Yoshida would be posted, and expectations were that he would get a multiyear deal with the winning bid at a low-eight-figure AAV, call it $35-50 million total as a contract, plus a posting fee.
That figure comes from teams projecting what the highest bid would be in an admittedly frothy free agent market. What that means is each team is marking up from what they actually think he's worth or would offer, imagining what the hypothetical team that likes him the most would do.
So you can then imagine the surprise across the industry when news broke that Yoshida signed with the Red Sox for five years, $90 million, plus a $15.4 million posting fee to his NPB club.