Roman Anthony extension should push Cubs to act fast with Matt Shaw

The Boston Red Sox and Chicago Cubs found themselves in similar positions after the MLB trade deadline, each team failing to make the move that would have cemented their standing for the 2025 season. Craig Breslow, the former Cubs' executive running the baseball operations for the Red Sox, has drawn comparisons to Jed Hoyer for his frustratingly stubborn approach, but he just did something that Hoyer has never been able to achieve during his time in Chicago.

Jeff Passan of ESPN was first to report that the Boston Red Sox have agreed to an 8-year contract extension with outfielder Roman Anthony.

Cubs better learn from the Red Sox before it’s too late with Matt Shaw

Anthony was the top prospect in baseball before he made his MLB debut with the Red Sox earlier this season, and is beginning to find his offensive approach. Anthony entered Wednesday with a wRC+ of 133 through his first 190 plate appearances with 2 home runs. Assuming that Anthony continues that development, the deal looks like an early steal for the Red Sox.

As it pertains to the Cubs, they likely missed their opportunity at this type of extension with Pete Crow-Armstrong. The 2025 season has been a breakout campaign for Crow-Armstrong, who has floated with being a National League MVP candidate. Considering that reality, Crow-Armstrong's next contract is quickly approaching the $200MM range.

While the opportunity may have been missed with Crow-Armstrong, the Cubs still have the chance to take this approach with third baseman Matt Shaw. Having this conversation before the All-Star break likely would have had anyone laughed at, considering Shaw was on the verge of being replaced as the Cubs' starting third baseman.

However, since the All-Star break, Shaw has been the hottest hitter in the Cubs' lineup. A smaller sample size than what the Red Sox had with Anthony, Shaw has a 186 wRC+ with 5 home runs in 51 plate appearances since the break. While Shaw was never the top prospect in baseball, he was quickly approaching Top 20 status by the time he graduated to the Major League level.

It's still slightly early to say the Cubs extending Shaw now is a genius move by Hoyer, but with his recent swing change, it's quickly headed in that direction, and something that might be discussed this offseason.

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