What would a Justin Steele contract extension with the Cubs look like?

DALLAS The Chicago Cubs and All-Star pitcher Justin Steele have not engaged in talks about a potential contract extension, according to league sources, but for both sides that could be a conversation worth having this winter.

The soaring cost of pitching emerged as an early offseason trend and continued through Major League Baseball s Winter Meetings this week in Dallas, where the New York Yankees reached an agreement with Max Fried on an eight-year, $218 million contract, the largest deal ever for a left-handed pitcher.

That appetite for more and more pitching is insatiable.

Advertisement The Athletics , a transient, low-budget franchise, handed Luis Severino a three-year, $67 million contract.

Nathan Eovaldi s three-year, $75 million deal with the Texas Rangers will take him past his 37th birthday.

Only a few months after Matthew Boyd struggled to get major-league offers following Tommy John surgery, the Cubs gave him $29 million guaranteed.

The #Cubs today have agreed to terms with LHP Matthew Boyd on a two-year major league contract.

Welcome to Chicago, Matthew! pic.twitter.com/cGyBQbWgrk Chicago Cubs (@Cubs) December 7, 2024 Fried has a larger body of work than Steele and a World Series ring from the Atlanta Braves , but the two lefties have performed at a similar level across the last two seasons.

During that time, Fried (6.1) generated more wins above replacement than Steele (5.6), per Baseball Reference, while Steele accounted for 56 more innings and made 11 more starts.

Steeles 3.07 ERA was almost identical to Frieds (3.04).

Timing is everything for a free agent, though, and Steele wont reach that status until after the 2027 season.

Its been a gradual climb for the homegrown pitcher, whos spent the past decade in the Cubs organization since getting drafted out of high school and undergoing Tommy John surgery early in his professional career.

The starting point would be what Steele should earn over his next three seasons in arbitration.

As a Super Two player based on service time, hes already at a nice perch: MLB Trade Rumors estimates hell get around $6.4 million for 2025.

From there, you could project an additional $22 million to $25 million for the 2026 and 2027 seasons, so lets round it to $30 million over the next three years total.

The best-case comp for Steele is probably Logan Webb , whose five-year extension with the San Francisco Giants valued three free-agent years at roughly $23 million per season.

Webb was worth 10.3 WAR (according to FanGraphs) in the three seasons leading up to that extension; Steele has been worth 10.3 over the last three years.

Advertisement The difference is age: Webb was 25 when he signed his extension and it covers his age-27 through age-31 seasons.

Steele is entering his age-29 season and is already under team control through his age-31 season.

Since the free-agent years are less likely to be prime years, Webbs deal probably represents the high end for Steele.

Kyle Freeland s five-year extension with the Colorado Rockies valued his three free-agent years at about $16 million per season.

That should be the low end, as Steele has been a more consistent left-hander than Freeland was at that point.

Like Steele, Cristian Javier had three years of team control remaining when he signed his extension with the Houston Astros , which valued two of his free-agent years at about $21 million per season.

Mitch Keller was a year closer to the open market when he inked his extension last spring with the Pittsburgh Pirates , and that too pays Keller about $21 million for his free-agent years.

A good sweet spot for Steele, then, could be a deal that values any free-agent years at roughly $22 million.

Buying out two of his free-agent years at that number would sign him through the age of 33 with a five-year deal worth about $74 million overall.

Adding one more year would make it a six-year pact for $96 million.

This process typically picks up around the January deadline to exchange salary numbers for next season, and the Cubs have traditionally used spring training to advance some of these negotiations.

Before and after Opening Day 2023, Jed Hoyers front office finalized extensions for second baseman Nico Hoerner and outfielder Ian Happ .

Right now, Hoyers group is intently focused on the trade market and more pressing roster issues, trying to upgrade a team that finished with 83 wins in each of the last two seasons.

Steele wouldnt necessarily be the only player the Cubs might want to have an exploratory conversation with, either.

But as this offseason has shown, it is always about pitching, and the price is going up.

(Photo: Nuccio DiNuzzo / Getty Images).

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