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The front offices of Boston and St. Louis have been on the phone with each other (or texting back and forth) all offseason, culminating in two big trades so far. 

Around Thanksgiving, the teams agreed to swap RHP Sonny Gray (36) along with $20 million for RHP Richard Fitts (26) and LHP Brandon Clarke (22, A+). 

Gray should play as a known quantity, and it sounds like he’s eager to pitch in the AL East again. “It’s easy to go to a place where it’s easy to hate the Yankees,” he said at this introductory press conference, instantly endearing himself to a new fanbase. He also restructured his contract to turn a guaranteed year into a mutual option that Boston can refuse for a $10 million payout. With the Cardinals covering $20 million, Gray will cost $11 million for the Red Sox in 2026. If he’s good for them, Boston can bring him back next year for $30 million at a $25 million luxury tax hit. 

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It’s Christmas week, and the yule stove is warm, so let’s gather around the fire of teams making transactions and poke at the coals. 

When Baltimore made the Grayson Rodriguez for Taylor Ward swap, we anticipated another move to clear the outfield logjam. That’s not exactly what happened next, but they did clear out a bunch of pieces and add a pitcher in sending several prospects to Tampa in exchange for Shane Baz. One thing makes this trade unique is that it’s basically three first-round picks and two prospects for Baz. I don’t think I’ve seen a trade in this shape. OF Slater de Brun and C Caden Bodine were first-rounders this year, and they added in the 33rd overall selection in next year’s draft along with RHP Michael Forret and OF Austin Overn. Bodine has played 11 games in Low-A, and de Brun hasn’t played yet in the pros. 

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1. OF Jacob Melton | 24 | MLB | 2025

A left-handed hitter listed at 6’2” 208 pounds, Melton at his hottest features speed, patience and power with serviceable defense in center field. His 2025 was interrupted a couple times by injuries, but he’s talented enough to push for a spot in spring. In 35 Triple-A games, he slashed .286/.389/.556 with six homers, 12 steals and a 20 percent strikeout rate. He withered under the bright lights, slashing .157/.234/.186 in 78 plate appearances spread across 32 games. 

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1. OF Walker Jenkins | 21 | AAA | 2026

The sixth overall pick in the stacked 2023 class, Jenkins is a left-handed hitter with power and plate skills listed at 6’3” 210 pounds, but as I say all the time around here, those measurements look a little out of date. He’s dealt with some injuries that have cost him reps but steadily climbed the organization ladder nonetheless, closing out 2025 with 23 games in Triple-A. In 84 games across four levels, he slashed .286/.399/.451 with ten home runs and 17 stolen bases. It’s tough to predict how the team will handle his timeline. They seem to go back and forth on trading Joe Ryan every other day. If they keep him, Jenkins could be up early. If they move him this winter, I’d bet they’ll slow-play their season in general. 

Here’s a link to Grey’s 2026 Fantasy Outlook for Walker Jenkins.

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Format = Position Player | Age on 4/1/2026 | Highest Level Played | Estimated Time of Arrival 

1. C Carter Jensen | 22 | MLB | 2025

Jensen is a left-handed hitting catcher at six-foot 210 pounds who plays good defense and employs an extremely patient approach in the batter’s box. His 20-game debut in 2025 could not have gone better. He slashed .300/.391/.550 with three home runs and 12 strikeouts against nine walks for Kansas City after posting a .290/.377/.501 slash line in 111 games across Double and Triple-A. It’s hard to project his playing time this season with Salvador Perez in town, but I think we’re looking at something like 500 plate appearances and an intriguing fantasy season. 

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1. SS Kevin McGonigle | 21 | AA | 2026

The 37th overall pick in the 2023 draft, McGonigle has great hands on both sides of the ball along with plus speed and burgeoning power. A left-handed hitter with a quick swing, he broke out in 2025, slashing .305/.408/.583 with 19 home runs and just 46 strikeouts against 59 walks  in 88 games across three levels. McGonigle has one of my favorite prospect traits in that hitting is the easy part for him. Detroit’s not an easy park for lefty power, but the pitching in that division is soft, so maybe it all comes out in the wash. 

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Format = Position Player | Age on 4/1/2026 | Highest Level Played | Estimated Time of Arrival 

1. OF Chase DeLauter | 23 | MLB | 2025

Here’s what Grey had to say the other day in his 2026 Fantasy Outlook for DeLauter: 

“He’s a monster lefty bat who takes a ton of walks. That’s who he is. It’s who he’s been for a few years. He went 7/1/.264 with a 15.8 walk and strikeout rate. Yes, 15.8% for both. He’s a .380 OBP guy with power. In my rookie outlook post for him last year, I said, “So, he’s old. Not like dinosaur old, but Chase DeLauter is 23 and played less than 40 games last year in the minors. Does he have proclivity for injuries? By the way, you can’t say proclivity aloud without sounding like Dr. Evil.”

Great take. You don’t even have to say it aloud. Once you put “proclivity” in your head with Dr. Evil’s voice, that’s the way it stays. And it’s fun. I kinda can’t stop doing it. Anyway, I think DeLauter is the front-runner for rookie of the year. Unless Cleveland sends him back to Triple-A again, where he would almost certainly get injured riding a bus or sleeping on a couch or picking a fight with a mascot who hits the gym a lot. 

PS: I’ve been watching TENET off and on today, and I feel like there’s a connection to DeLauter’s development path. I mean he just POOF appeared out of nowhere in the playoff lineup. Perhaps his timeline has been inverted. 

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1. OF Braden Montgomery | 22 | AA | 2026

Chicago has seen some of its prospects backslide, so the front office had to be thrilled to see Montgomery post respectable outcomes across three levels in his debut season, slashing .270/.360/.444 with 12 home runs and 14 stolen bases in 121 games. A switch-hitter at 6’2” 220 pounds, Montgomery was Boston’s first-round pick in 2024 (12th overall) but got dealt away in the Garrett Crochet trade before he even played an inning for the Bo Sox. Right field is wide open in Chicago, and while that probably shouldn’t accelerate this guy’s timeline, people have their own jobs to consider, so you never know. 

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1. RHP Trey Yesavage | 22 | MLB | 2025

Yesavage became something of a household name during Toronto’s titillating post-season run despite having pitched just 13 big league innings during the regular season. Part of that was because he was amazing and so were the Blue Jays, but some of that was likely because he has a unique style that’s easy for even a casual baseball fan to recognize. I don’t know if you’ll remember Josh Collmenter. I was surprised to remember him myself, but he’s the last guy I can remember releasing at the 12’o’clock slot this way. The thing about Collmenter was he lacked velocity, sitting in the mid-80’s with his fastball and cutter (84.6 mph in his final season). Nonetheless, he had a career ERA of 3.64 and WHIP of 1.198 in 695.1 innings despite recording just 494 strikeouts. Anywho, Yesavage has a similarly deceptive release point but also has more strength and balance throughout his delivery, which helps him command a three-pitch arsenal highlighted by a dynamic splitter that tunnels well with his fastball and slider. He also throws much, much harder than Collmenter ever did, averaging 94.7 mph on the fastball, 88.7 on the slider and 84.1 on the splitter. His slowest pitch is the same speed as Collmenter’s fastest. Fun stuff. Great comp. I baseball writer. But seriously folks, I think Yesavage is going to be awesome. Heck, he already was. 

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1. SS Carson Williams | 22 | MLB | 2025

Featuring double-plus defense and easy power from the right side, Williams figures to open the season as the everyday shortstop for Tampa. I’ve always been low on him compared to the places he’s been ranked in most public facing places because he’s always struck out enough that I feel compelled to pump the brakes. In 32 MLB games, he slashed .179/.219/.354 after slashing .213/.318/.447 in 111 Triple-A games. Wait, should he even be atop this team’s list? Yeah, I think the proximity and power-speed upside warrants the spot. Plus there’s really nobody here to knock him off the top. I just don’t really want him on my teams. 

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1. OF Spencer Jones | 24 | AAA | 2026

At 6’7” 240 pounds from the left side, Jones is a fantasy darling for his combination of power and speed. The 25th overall pick in the 2022 draft, he came just one steal shy of a 30/30 season in 116 games across two levels in 2025, slashing .274/.362/.571 with 35 home runs, 29 stolen bases and a 35.4 percent strikeout rate. That last piece might not matter much given how much impact Jones makes on contact, but it creates enough doubt to keep me skeptical, despite what his ranking here suggests. The upside is just too enticing and near to ignore. 

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1. SS Franklin Arias | 20 | AA | 2027

Arias signed for $525,000 as the second highest paid player in Boston’s 2023 international class. Today, that looks like money well invested. A right-handed hitter listed at 5’11” 170 lbs, Arias wasn’t as good in 2025 as he had been the year before, but he was facing much older competition and still managed a 108 wRC+ in 87 High-A games despite slashing .265/.329/.380. The plate skills were still elite: 8.2% walk rate against an 8.9% strikeout rate, so the organization waved him along to Double-A for a ten-game stretch at season’s end. He hits the ball hard enough. Just needs to add some loft and grow into some man-strength. 

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