The Cubs appear to be lagging behind the times when it comes to extending contracts for young, gifted players. This is one of the reasons Ian Happ is entering his walk year and why the World Series core was all traded.
I’ve written here on the possible terms of an extension for Nico Hoerner’s contract and Ian Happ’s.
However, what about making a pitch? The Cubs may soon need to consider locking up young pitching talent for the long run, as they have recently placed a lot of emphasis on drafting pitchers. Naturally, pitchers are more vulnerable to unfavorable injuries than position players, which may be why there aren’t as many of these deals.

A possible contender for such a contract would be Justin Steele, who had a career year in 2022—1.49 ERA, 1.233 WHIP, and 65 strikeouts in 54⅓ innings—especially over his last 10 starts.

I searched the market to see what kind of similar pitchers have signed long-term contracts recently. I located two.

I believe the Cubs could work out a deal like that for Steele, who won’t be eligible for arbitration until 2024. Though he only made 24 starts and sustained a back injury in late August, Steele’s 2022 season was still worth a respectable 2.0 bWAR, better than Ashby’s 2022 season, which saw Ashby record negative bWAR with the Brewers.
I would therefore suggest an arrangement akin to Ashby’s. The following is stipulated in his contract, in addition to a $1 million signing bonus.

Shortly after the season concluded, the Braves signed Spencer Strider to a six-year, $75 million contract, with the possibility of a seven-year, $97 million extension if an option is taken.

Even though Steele seems good right now, Strider is a better pitcher right now. He had a more successful 2022 campaign and came in second in the NL Rookie of the Year competition. The Cubs will not give Justin any money.

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