The Rundown Lite: Maton’s Deal, Gray to Red Sox, Helsley’s Market Growing

Before anyone accuses me of mailing this one in, I’ll just tell you I’m mailing it in. This will be a series of brief topics rather than one or two deep dives, as I’m trying to get a few things wrapped up before Thanksgiving break gets started. On that note, I got an early start on the holiday festivities by watching the 1st grade balloon parade this morning at the local elementary school where I volunteer as a reading mentor.

That was about as far removed from doom scrolling as possible, and it felt good to clap and smile as the kids went down the hall. What a great way to adjust my perspective for the day. Now, on with the show.

Maton Gets Paid

Phil Maton has a chance to more than double his previous career earnings with his new Cubs contract, which Jon Heyman was first to report is worth a guaranteed $14.5 million. If he’s able to reach annual incentives of $250,000 based on appearances, he can make more in the next two years than he had in the previous nine. My guess is that he’s got to reach 60 games to max the bonuses, a mark he’s exceeded in each of the last five seasons.

No word yet on the exact terms of those incentives or whether the club option for 2028 is for the same $7.25 million AAV, so we’ll update this once more is known. Maton was not among MLB Trade Rumors’ top 50 free agents, and thus didn’t have a contract prediction, but righty reliever Emilio Pagán at No. 46 was projected to get a two-year, $16 million deal. Pagan is nearly two years old and hasn’t been as consistent as Maton, so the Cubs may have gotten a relative bargain.

Like Matthew Boyd last season, this looks like a case of the front office having identified an undervalued pitcher they liked enough to jump his market. We should find out soon whether this signals a philosophical shift in bullpen construction or is just an aberration.

Gray Back to AL East

Righty Sonny Gray appears to be tailing off as he heads into his age-36 season, the last of his current deal, so the Cardinals were desperate to move him as they rebuild and get younger. That’s why they were willing to eat $20 million of salary in a deal that sees them getting lefty Brandon Clarke and righty Richard Fitts from the Red Sox.

Dick Fitts, eh? That’s what she said.

Anywho, Ken Rosenthal reported that Gray is restructuring his $35 million salary for 2026 with a $5 million buyout on a 2027 club option to $31 million with a mutual option for 2027 that includes a $10 million buyout. So he just got a $1 million raise and he doesn’t have to play for the Cardinals, which is some serious winning. As for who won the trade, I might have to give it to St. Louis.

They just shed an aging starter for a 22-year-old southpaw ranked No. 5 in Boston’s system and a 26-year-old righty who has some MLB experience under his belt. Fitts missed time in 2025 with a right pectoral strain and right arm neuritis, but he’s reportedly at full health this offseason.

This will be Gray’s second stint in the AL East after spending a disappointing year and a half in New York, during which he struggled within the Yankees’ rigid pitching infrastructure. He rebounded in Cincinnati and got even better in Minnesota before becoming one of several mid-30s starters the Cards signed for 2024 and beyond. This could work out really well for Boston if Craig Breslow and his crew can foster another change-of-scenery bounce.

Who’s Next to Flee STL?

The Cardinals wanted to trade Gray last year, same for Nolan Arenado and perhaps Willson Contreras. No-trade clauses kept getting in the way, narrowing their potential suitors to those who would be acceptable to the players in question. Arenado was particularly stubborn, vetoing a potential deal to Houston that probably would have worked out much better for him.

I’d expect Cards POBO Chaim Bloom to remain aggressive in clearing other vets from the books, and for said vets to do what Gray just did. Unless Arenado has lost any desire to win after getting paid several years back, this could be his last chance to play for a winner. He’ll turn 35 in April and his production has fallen off dramatically as his bat speed can no longer make up for his above-average swing length, so any trade will have to see the Cards eat money to find him a situation he finds amenable.

More Notes

• Former CI contributor Brendan Miller listed Taylor Rashi, Colin Snider, and Shaun Anderson as under-the-radar pitchers who might interest the Cubs on minors deals.
• Patrick Mooney reports that the Cubs indeed “among the teams showing interest” in reliever Ryan Helsley, though, as noted yesterday, interest in him as a starter could push him out of their price range.
• Katie Woo of The Athletic noted that “roughly 15 teams” have already expressed interest in Helsley, with the Tigers talking about a starting role and others proposing multiyear deals as a setup man or closer.
• Yankees owner Hal Steinbrenner told MLB.com’s Bryan Hoch that it’s “not a fair statement or an accurate statement” to say his team makes a profit. In that case, I’m sure he won’t mind opening up his books.
• The Cubs named Jonathon Long their Minor League Player of the Year and Jostin Florentino their MiLB Pitcher of the Year. It’s wild to me that the latter was up to 90 mph last year after sitting around 85 mph in 2024; that kind of velo may not even earn you a spot on a JV team at some high schools.

Content Consumption Requests

In the interest of mailing it in, I’m not even going to provide a trailer, review, or suggestion today. Instead, I want to know what you’re watching, reading, and listening to. Anything new and cool, maybe something tried and true? Share it with us in the comments.

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