CHICAGO -- If only the designated hitter rule had come to the National League prior to 2022. It could have changed the course of Japanese two-way star Shohei Ohtani's career -- as well as the trajectory of the Chicago Cubs. At least that's what the Cubs were thinking when they pursued him back in 2017, before he signed with the Los Angeles Angels.

"It was pretty clear he wanted to do both [hitting and pitching], and DHing was the best option for that," Cubs president of baseball operations Jed Hoyer said last week at the general managers meetings. "As good as the meeting with him went, we always knew it was going to be an uphill climb."

The Cubs were one of seven finalists for Ohtani's services back then -- and one of two not located on the West Coast. At the time, Chicago was in the middle of a winning window, having made the NLCS three straight seasons, taking home a World Series championship in 2016.

"We had things rolling pretty well at that point," Hoyer said. "I think he was intrigued."

So were the Cubs.

Ohtani, now the biggest free agent in the history of the sport, is deciding where he wants to play next, and the Cubs are again interested in courting him, according to sources familiar with the situation.

Ohtani is expected to win his second American League Most Valuable Player Award when winners are announced Thursday evening. Everyone knew he could pitch, but what he's done at the plate over the past six seasons has been eye-opening -- for fans and executives alike.

"There were zero questions about his ability on the mound," Hoyer recalled. "The offensive part of his game was underestimated."

There will be plenty of competition for Ohtani this winter, but at least Chicago has the DH to offer this time around. It also just hired widely respected manager Craig Counsell to take over an 83-win team that just missed the postseason in 2023. Additionally, the team has payroll coming off the books in the form of Jason Heyward ($21 million) and Cody Bellinger ($17.5 million), leaving money for a massive deal. The Cubs were under the luxury tax threshold in 2023, ranking 11^th in payroll, making it a little less undesirable to exceed it, if necessary.

The timing could finally be right for a Cubs-Ohtani union.

"Ohtani would own Wrigley Field, literally," one NL scout joked about his potential salary. "He'd own Chicago, for sure."

What Ohtani pursuit means for Bellinger

Bellinger was a 2023 success story. Signed to a one-year deal by Chicago before the season, he won a Silver Slugger Award, along with Comeback Player of the Year honors after compiling a 133 OPS+. And he played great defense, both in center field and at first base. He accomplished what he set out to do in coming to Chicago: Rebuild his value and head back to free agency.

"There's broad interest in Cody Bellinger," his agent, Scott Boras, said recently. "Cody had a great experience in Chicago. He can play well anywhere. A lot of this has to do with ownership. It has to do with their commitment."

The Cubs seem committed to spending money this offseason, especially after signing Counsell to a five-year, $40 million contract, a record for a manager.

"I saw quickly that the organization is in great health," Counsell said. "There is momentum happening here."

But while a pairing of Ohtani and Bellinger would be a dream scenario for fans, it's unlikely. Multiple sources think the Cubs are more likely to sign Ohtani than bring Bellinger back on his own massive deal.

"I think Bellinger is as good as gone," one source familiar with the situation said at the beginning of the offseason.

Circumstances and history are two reasons the Cubs and Bellinger may not reunite. First, there likely will be teams not in the mix for Ohtani that are desperate for the next-best left-handed bat available. The New York Yankees were interested in Bellinger at the trade deadline and will be again, according to sources familiar with their dealings. The Toronto Blue Jays have been missing a dangerous left-handed hitter as well. The San Francisco Giants also are among Bellinger's suitors.

Under Hoyer and owner Tom Ricketts, the Cubs have been measured in their dealings with free agents. Setting Ohtani aside, the organization isn't the type that gets into bidding wars. And it won't for Bellinger, according to sources familiar with the situation.

Another side to the narrative involves Boras and Ricketts personally. They don't have the type of relationship where the agent can pick up the phone and negotiate with the owner like Boras has done in other situations.

To wit: The Cubs have not signed a Boras client to a multiyear deal in a very long time. That includes players on the free agent market, ones they've drafted who have won an MVP (Kris Bryant) or those they've traded for who have won a Cy Young Award (Jake Arrieta). They've all moved on. Bellinger is likely to as well.

Boras was asked if the timing of a Bellinger deal is related to Ohtani, who is represented by a different agency.

"Bellinger is a position player, Shohei is a DH, so those platforms of demand are very different," Boras said. "Teams that are approaching Cody are teams that want him to play every day in the field. They may go for a DH and Cody, but their [paths] don't cross because of that reason."

Ohtani isn't the only missing piece

Whether Ohtani becomes a Cub or not, the team has other holes to fill, including potentially at first and third base, as well as its starting pitching. They can dip down into their farm system for a trade, if necessary, as it's as strong as it's ever been, ranking second in ESPN's Kiley McDaniel's latest analysis.

The team also has power-hitting infielder/outfielder Christopher Morel playing first base during winter ball in an attempt to find a home for him around the diamond. If the New York Mets were to make Pete Alonso available for a trade, the Cubs could be a fit, with Morel as a centerpiece player in return, according to sources familiar with their thinking.

But Alonso recently switched agents to Boras -- who is also San Diego Padres outfielder Juan Soto's agent. Both players will be free agents after 2024, and while a trade-and-sign deal for either player sounds sensible, it's unlikely.

"I don't think any player wants to play in an organization that he does not know," Boras said. "That's the normal course."

In other words, playing out the year, then testing the free agent waters is more than likely for Alonso and Soto -- unless they sign back with their current teams. New Mets president David Stearns also said he expects Alonso to be his starting first baseman on Opening Day -- though, a lot can change between now and then.

At third base, a Cubs reunion with veteran Jeimer Candelario doesn't seem likely, according to a source familiar with the situation. Interest in Candelario should be high coming off a career-type year, with Toronto and his old team, Washington, already showing some. Former second baseman Nick Madrigal played admirably at third for the Cubs when he was healthy last season, but he probably isn't the everyday option there moving forward.

The Cubs are also in on Japanese pitchers Yoshinobu Yamamoto and Shota Imanaga -- the latter has already spent time in Chicago -- according to sources familiar with the situation. They also have an eye on Milwaukee starter Corbin Burnes, in case the Brewers begin to subtract -- and Milwaukee is willing to trade with the team that just pilfered its manager. The Cubs would like to acquire a starter after Marcus Stroman opted out of his deal recently -- though young pitching is a sudden strength for the organization. Minor league righty Cade Horton could end up being the top pitching prospect in baseball next year, according to McDaniel.

But the big fish is still Ohtani. Like all his suitors so far, the Cubs are keeping their strategy close to the vest.

"It didn't surprise me in the end, he picked an AL team," Hoyer said about the 2017 sweepstakes, "but wish we could roll back the clock and take a shot at it again."

Sometimes second chances never materialize, but six years after attempting to woo him the first time, the Cubs are getting another shot.