Despite his status as the most famous baseball player on earth, Shohei Ohtani remains a man of mystery.

Since his 2018 MLB debut, the two-way Japanese dynamo has catapulted himself into global superstardom. Ohtani has become a household name on both sides of the Pacific, captivating sports fans with a blend of awe-inspiring athleticism and easy-going charm. In 2023, the most valuable free agent in the game’s history made approximately $40 million on endorsements alone, a number that’s sure to grow in the coming years as he (probably) enters a new market.

But despite all the attention, Ohtani has maintained his privacy. We know precious little about the two-time MVP’s life beyond the ballpark. That’s by design. There have never been any dating rumors. His parents are never shown on TV broadcasts. A GQ video from January 2022 titled “10 Things Shohei Ohtani Can’t Live Without” includes seven baseball-related items (bat, glove, cleats, compression pants, ice machine, heart rate monitor, iPad), two sleep-related items (fancy pillow, sleep mask) and his cell phone.

That’s not to say Ohtani’s quiet, humble nature is a bad thing. It’s undeniably genuine, and he’s more than spectacular enough on the diamond that he doesn’t need to be overtly fame-seeking in his free time. Just because he’s not dating a Jenner or rolling up to the Met Gala in a onesie doesn’t mean he’s not a star.

But his reserved persona does help to contribute — alongside the language barrier — to a haze of uncertainty regarding his current free agency. That’s also by design.

Ohtani and agent Nez Balelo, his main representative at CAA, don’t want a drama-filled circus and have treated the entire process like a state secret. That strategy has turned the Ohtani sweepstakes into a rumor desert; teams were reportedly told that if news of a meeting leaked, that would be held against them come decision time.

But there is one extremely telling data point worth investigating: Ohtani’s initial free agency.

Remember 2017? When Ohtani shocked the world and chose the Angels? Before he thrilled the sporting world with his two-way prowess? That process, and the messaging around it, is extremely helpful. Yes, much about Ohtani (and MLB) has changed since then, but if we want to know how Ohtani might approach free agency, his previous trip to the somewhat open market feels like a good place to start.

Let’s review the context.

After the 2017 season, Ohtani’s NPB club, the Nippon Ham Fighters, posted their superstar by his request. Ohtani was only 23 at the time, which meant he was subject to MLB bonus-pool restrictions regarding international amateur free agents. If he had waited two more seasons, he would have been considered a “normal” free agent. By leaving Japan when he did, Ohtani left around $200 million on the table. He received a $2.315 million signing bonus, the highest figure the Angels could offer, and was subjected to MLB’s typical pay scale for his first six seasons.

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Ohtani’s decision to forgo such a massive payday solely because he felt he was ready for the biggest stage is incredibly abnormal. It’s overly simplistic to claim that he “doesn’t care about money” because of what happened six years ago, but not many pro athletes would make the same choice.

This time around, Ohtani is likely to receive a record-breaking amount of money. The average annual value could tickle the $50 million dollar mark. Unless he wants a slew of opt-outs, the contract will likely stretch well into the next decade. He’s not signing a team-friendly, two-year deal with the Pirates because he likes the view. But there’s a belief around the industry that the difference between a few million dollars is not going to be the deciding factor here. CAA will try to squeeze every dollar out of whomever Ohtani chooses (as they should), but the highest bidder is not a lock to win the auction.

So, then, what matters to Ohtani? Let’s toss it to the statement Balelo released when his then-unproven client picked the Angels.

 “While there has been much speculation about what would drive Shohei’s decision, what mattered to him most wasn’t market size, time zone or league but that he felt a true bond with the Angels. He sees this as the best environment to develop and reach the next level and attain his career goals.”

There’s a good chance that Ohtani’s “career goals” have shifted since then. At the time, he was primarily focused on a comfortable transition to the big leagues as a two-way player, a process only Amercian League teams could offer with the old DH rules and the Angels ultimately succeeded in facilitating. Now that there are two MVPs in his trophy case, perhaps Shohei wants to join a more competitive outfit that can increase his playoff chances. Either way, the chatter about location and market size this time around feels similarly unimportant. He’s going to go with his gut again.

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The process six years ago was much swifter than you might remember. Ohtani was officially posted on Dec. 1st, narrowed it down to seven finalists on Dec. 4th and reportedly agreed to join the Angels on Dec. 8th. In retrospect, the speculation about those seven finalists — the Padres, Dodgers, Angels, Cubs, Rangers, Giants and Mariners — felt like it lasted for a month.

At the time, there was a notable omission from that group: The New York Yankees.

Yankees fans were peeved that the most sought-after Japanese talent in history wouldn’t even agree to a sit-down with the club’s front office. Knowing what we know now about Ohtani’s preference for privacy, it makes sense that he would avoid playing for the sport’s most meticulously covered team.

It’s unlikely the Yankees have done anything in the past six seasons to change Ohtani’s mind. Admittedly, that’s conjecture, but there are many around the league who would consider it an absolute shock if Ohtani ended up in pinᵴtriƥes.

It’s nearly impossible to determine what Ohtani is looking for this winter. Trying to pin down his preferences and motivations is like a game of hallucinogenic darts. We, the baseball prognosticating community, really don’t know jack. Neither do many inside the game. Ohtani is an enigma, wrapped in a conundrum. Only time will reveal the truth. All we can really do is wait and speculate.