'I don’t think the desperation is there the same way it is with the Blue Jays,' Jeff Passan on whether or not the Cubs will re-sign Cody Bellinger

We’re only a couple of weeks away from Spring Training games being played and four of this winter’s top free agents still don’t know where they’re going to be playing.

This isn’t a coincidence, as Matt Chapman, Cody Bellinger, Blake Snell, and Jordan Montgomery are all represented by superagent Scott Boras, a negotiator who isn’t afraid to have his clients wait for the deal that they’re looking for.

Back in 2019, Bryce Harper waited until March 3 to sign a 13-year, $330 million contract with the Philadelphia Phillies, which was the largest free-agent contract in baseball history at the time. A few years before that, Stephen Drew didn’t re-sign with the Boston Red Sox until over one month into the 2014 season after helping the team win the World Series the year prior.

With that in mind, it wouldn’t be that surprising to see any of the four aforementioned Boras clients still left on the board when Grapefruit and Cactus League games are being played. Also, given the fact that there are more big-name free agents than high-spending teams left, Boras might not be able to get all of the deals that he’s looking for.

Insider Jeff Passan spoke on ESPN 1000 in Chicago on Wednesday and noted, in the context of the Cubs, that the team shouldn’t be in a rush to re-sign Bellinger because the current market is more favourable to teams than free agents.

“The relationship with the Cubs is there and it’s real,” Passan said. “I think one thing we know about [Cubs President of Baseball Operations] Jed Hoyer at this point, he’s got a price in mind and he will be willing to pay it and be aggressive in that regard but he’s not going to go chasing something. Right now I don’t blame him for one second because the leverage it feels like is with teams at this point.”

When it comes to Boras’ two position marquee players, Bellinger and Chapman, there have been three teams who have been frequently mentioned as interested in either one or both — the Cubs, Toronto Blue Jays, and San Francisco Giants.

The Blue Jays could use either player, as Chapman would be an upgrade on an underwhelming platoon mapped out for third base and Bellinger would be a big bat for centre field that moves Kevin Kiermaier to a more comfortable fourth outfielder position. The Cubs and Giants, meanwhile, are both middling teams who could use star power in their lineup, so a case can be made for either team to sign either Bellinger or Chapman.

Where these players wind up at this point is anybody’s guess, but Passan noted that the Blue Jays seem to be more desperate than others to make a splash.

“I just feel like the Toronto Blue Jays need Cody Bellinger more than the Cubs do,” Passan said. “I do think the Cubs are gonna sign one of the four Boras guys. I think with Bellinger, they don’t want to go seven or eight years. They don’t want to go $200+ million.

If the price comes down on that, if they could do a shorter-term deal, if they could do something with opt-outs then, yeah, maybe it becomes more attractive to them. But I don’t think the desperation is there the same way it is with the Blue Jays.”

The Blue Jays came into this off-season on the heels of another sweep in the Wild Card round of the playoffs, pushing the team to 0-6 in the playoffs during the Vladimir Guerrero Jr. and Bo Bichette era. That letdown was followed up by a rollercoaster ride that saw reports saying that Shohei Ohtani was on his way to Toronto to sign with the Blue Jays before ultimately signing with the Los Angeles Dodgers.

If the Blue Jays are indeed feeling desperate to make a splash to convince their disgruntled fans to buy tickets to fill up their newly-renovated stadium, they haven’t presented that way. The team has added Justin Turner and Isiah Kiner-Falefa to its lineup this winter, fine replacements for Brandon Belt and Whit Merrifield, but far from the upgrade that fans were hoping for.

General manager Ross Atkins has mentioned multiple times that the Blue Jays like the group that they have and that they believe that last year’s poor results offensively were an anomaly. Ben Nicholson-Smith also noted in an article for Sportsnet last week that the Blue Jays have “completed most or perhaps even all of their off-season shopping.”

When you put it all together, this seems like one giant game of chicken between a handful of teams and an agent representing multiple players. The Blue Jays would surely love to add either Bellinger or Chapman, but they’re only going to do so if they can win the staring contest and get the deal signed with the number that they want.

Who’s going to balk first? Are the Blue Jays actually the most desperate party in this situation?