The Cubs are eyeing a second chance to sign Shohei Ohtani

“It was very clear that 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 general managers meetings. “As far as the meeting went with him, we always knew it was going to be an uphill climb.”

The Cubs were one of seven finalists for Ohtani’s services at the time — and one of two not on the West Coast. At the time, Chicago was in the midst of a winning streak, having reeled off three straight seasons in the NLCS, and captured the World Series in 2016.

“Things were going well at that point,” Hoyer said. “I think he was intrigued.”

So were the Cubs.

Ohtani, now the oldest free agent in the history of the sport, is the one to decide where he wants to play next, and the Cubs are once 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 the winners are announced Thursday night. Everyone knew he could pitch, but what he did at the plate over the past six seasons was intriguing — to fans and executives alike.

“There were no questions about his ability on the mound,” Hoyer recalls. “The offensive part of his game has been underrated.”

There will be plenty of competition for Ohtani this winter, but at least Chicago has a DH to offer this time. 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 got payroll off the books in the form of Jason Heyward ($21 million) and Cody Bellinger ($17.5 million). dollars). million), leaving the money for a huge deal. The Cubs were under the luxury tax threshold in 2023, ranking 11th^y in the payroll, making it undesirable to override it, if necessary.

The timing may finally be right for the Cubs-Ohtani union.

“Ohtani will own Wrigley Field, literally,” one NL scout joked about his potential salary. “He’ll own Chicago for sure.”

What Otani’s pursuit of Bellinger means

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

“There is widespread 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 appear committed to spending money this offseason, especially after signing Counsell to a five-year, $40 million contract, a manager’s record.

“I quickly saw that the organization was in good 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 believe the Cubs are more likely to sign Ohtani rather than bring Bellinger back to his mega deal.

“I think Bellinger is in good shape as he left,” a source familiar with the situation said at the beginning of the season.

Circumstances and history are two reasons why the Cubs and Bellinger will not return to the Union. First, there are likely to be teams not in Ohtani’s lineup that would desperately want the best left-handed bat available. The New York Yankees were interested in Bellinger at the trade deadline and would do so again, according to sources familiar with their dealings. The Toronto Blue Jays are also missing a dangerous left-handed hitter. The San Francisco Giants are also among Bellinger’s suitors.

Under Hoyer and owner Tom Ricketts, the Cubs have been measured in their dealings of free agents. Ohtani aside, the organization is not the type to get into bidding wars. That won’t be the case for Bellinger, according to sources familiar with the situation.

The other side of the narrative concerns Boras and Ricketts personally. They don’t have the kind of relationship where an agent can pick up the phone and negotiate with the landlord like Boras has done in other situations.

To wit: The Cubs haven’t signed a Boras client to a multi-year deal in a very long time. This includes players on the free agent market, players they drafted who won an MVP Award (Kris Bryant) or those they traded for who won a Cy Young Award (Jake Arrieta). They have all moved on. Bellinger likely will, too.

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

“Bellinger is a position player, and Shohei is a DH, so those calling pads are completely different,” Boras said. “The teams that approach Cody are the teams that want him to play every day in the outfield. They might go for a DH.” And Cody, but their [paths] Do not cross for this reason.”

Ohtani isn’t the only piece missing

Whether Ohtani becomes a Cub or not, the team has other holes to fill, including potential at first and third base, as well as a starting spot. They can dip into their farm system to trade, if necessary, because he is as strong as he has ever been, ranked No. 2 in ESPN’s Kelly McDaniel’s latest analysis.

The team also has shortstop/outfielder Christopher Morrell playing first base during winter ball trying to find his home around the diamond. If the New York Mets were to make Pete Alonso available for trade, the Cubs could be a fit, with Morell as a starter in return, according to sources familiar with their thinking.

But Alonso recently switched his agents to Boras — who is also the agent of San Diego Padres outfielder Juan Soto. Both players will be free agents after 2024, and while a trade and sign deal for either player seems plausible, it is unlikely.

“I don’t think any player wants to play in an organization they don’t know,” Boras said. “This is the normal course.”

In other words, it is very likely that Alonso and Soto will continue to see out the year and then test the waters on the loose, unless they re-sign with their current teams. New Mets president David Stearns also said he expects Alonso to be his first baseman on Opening Day — although a lot can change between now and then.

At third base, the Cubs do not appear likely to reunite with veteran Jimmer Candelario, according to a source familiar with the situation. Interest in Candelario should be high after a career-high year, with Toronto and his old team, Washington, already showing some interest. Former second baseman Nick Madrigal played admirably at third for the Cubs when healthy last season, but he may not be an everyday option there moving forward.

The Cubs also field Japanese pitchers Yoshinobu Yamamoto and Shota Imanaga — the latter of whom has spent time in Chicago already — according to sources familiar with the situation. They also have an eye on Milwaukee’s Corbin Burns, should the Brewers start pitching — and Milwaukee is willing to trade to the team that just stole its manager. The Cubs want a starter after Marcus Stroman recently opted out of his deal — although young pitching is a surprising strength for the organization. Minor league outfielder Cade Horton could become the best prospect in baseball next year, according to McDaniel.

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

“It didn’t surprise me that in the end he picked the AL team,” Hoyer said of the 2017 lottery, but I wish we could turn back the clock and try again.

Sometimes second chances never happen, but six years after they tried to lure him the first time, the Cubs are getting another chance.