This Tarik Skubal contract prediction is the only one that gives Cubs a seat at the table

The impression is that the Chicago Cubs, on the surface level, are going to be involved in Tarik Skubal's market. No one expects the Cubs to outbid the Los Angeles Dodgers or the New York Mets, and if the latest intel from Jeff Passan is accurate, even the Cubs themselves don't think they can. It begs the question then, if the Cubs want Skubal "badly", what will their pursuit look like?

The idea of the Cubs giving Skubal the most years and overall money should be ruled out. This is a team that has yet to hand out a deal north of $200 million. Considering the expectation is that Skubal's contract will reset the market for starting pitchers, the Cubs are already behind the eight ball. Add in the assumption that Scott Boras is looking to make history with Skubal's contract, and it's going to be an uphill climb for Jed Hoyer and Co.

For a starting pitcher, not including Shohei Ohtani, the largest deal ever handed out was Yoshinobu Yamamoto's 12-year deal with the Los Angeles Dodgers worth $325 million. At the very least, that feels like the starting point for Skubal and Boras this offseason. But assuming the Cubs don't want to go to that level, then they will have to get creative with the AAV.

Projecting the Cubs' Tarik Skubal contract offer if Jed Hoyer doesn't alter his philosophies

But, knowing what is going to be on the table for Skubal, the Cubs will need to go out of their way to make their offer stand out. In other words, they will have complete shatter the previous AAV record for a starting pitcher. The record AAV for a starting pitcher is $43.3 million, held by Max Scherzer's previous contract with the Washington Nationals and Justin Verlander's previous contract with the New York Mets.

With the competition the Cubs are facing in the sweepstakes for Skubal, they can't just go over the record, they have to shatter it. Along those lines, assuming Jed Hoyer doesn't step dramatically outside of his comfort zone, it feels like an offer would look like four years for $250 million. That gives Skubal a record AAV of $62.5 million, but the Cubs probably can't just stop there. If they aren't giving Skubal the most years or overall money, they will likely need to tack on a player option for a fifth season that includes a hefty buyout.

The short-term, high-AAV contract structure is something that the Cubs have always been rumored to love, but previous free-agent markets, outside of last year with Kyle Tucker and Dodgers, haven't trended in that direction. It's why, even if the Cubs get creative with this type of offer for Skubal, it feels like they will still come up short.

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