Pimp My Dynasty: From Middle to the Money
Injuries wrecked a promising 2025, armed with power prospects, it's time for this Red Sox fan to make a move up the standings
This is part of a post series that John Allen is writing. He had dynasty owners with clunker teams send in the details on their leagues and teams. Below, John offers some advice on how to start righting the ship.
I grew up in a Tom Coughlin household, where early was on time and on time was late. So I appreciate punctual people.
For this Pimp My Dynasty Team idea, there were going to be many firsts. Colin was the first to fill out a form, first to complete email questions, and the first team I tried to Pimp.
Colin, who has been playing fantasy baseball since 2016, had a team in fourth place in the middle of the season until the wheels came off. He did the smart thing, dealing away parts for prospects, landing two of the best teenagers in Jesus Made and Sebastian Walcott, and finishing 10th of 20 teams.
This year, the goal is a top-five finish. With these categories in a head-to-head categories league, including a Rule 5-like protect and/or pillage draft before the FYPD, it’s a little complicated.
Here’s what I sent to Colin:
As I said before, you have a very strong group of hitting prospects and I think your trade targets should be teams that are looking to rebuild and have the players you are looking for to get back in the money. But as you will see, I think you could make a deal with last year’s champ.
PITCHING
Given the current categories for pitching and being in a H2H league, focusing on a handful of very good starting pitchers and stuffing your team with a mix of relievers with excellent K/9 stuff who will be pitching in hold and save situations is the key to 2026 success.
You have three starting pitchers who fit what you should be looking for: Bryan Woo, Robbie Ray, and Shane Smith. I don’t think David Festa is one of those guys, but at 25, I’d probably hold onto him for 2026 to find out. Christian Scott or Hunter Barco might be one of those guys, but I would look into finding a veteran arm who may be a little undervalued in 2026. Sonny Gray, Chris Bassitt, and Zac Gallen fit that mold.
Since you sent me the roster for the league champs, and he has Gray and Bassitt, I wonder if he would flip those older arms for a young SS prospect he lacks. Given all your SS prospects, maybe you can get both Gray and Gallen for Luis Pena or Bryce Rainer.
As far as high-leverage relievers, you have four guys I like on the roster: Justin Sterner, Reed Garrett (although you’ll need to wait for 2027 since he had TJ surgery), Bryan King, and Greg Weissert.
Looking to make deals, again probably dealing from your surplus of hitting prospects, for arms such as Kenley Jansen (he’s going to be the closer somewhere), Phil Maton, Ryan Helsley, Brad Keller, Edwin Uceta (love him for this role), Bryan Baker (especially if Griffin Jax goes to the rotation), Jordan Leasure (think he’s the White Sox closer this year), Jeremiah Estrada, Robert Garcia (might be a bargain after blowing up in the middle of last year), Garrett Whitlock (especially if Red Sox sign FA SP), Alex Vesia (if he can stay healthy again), Jeff Hoffman (even if he’s not the closer, he’s going to get holds), Dylan Lee, Jared Koenig, Gabe Speier, Andrew Kittredge (sneaky closer), Camilo Doval (it will be a wild ride), Erik Sabrowski (roles are well-defined in Cleveland and he should be the 6th/7th-inning guy), Connor Phillips (that Reds’ bullpen has a lot of openings), A.J. Minter (coming off hip injury), and Brant Hurter.
HITTING
As far as hitting goes, you are looking for sluggers who take walks. At this point your roster is mostly punting on steals. I’m not sure how the rest of the league approaches steals, but finding a hitter who could steal a couple bases a week, would be good.
I like Ben Rice (especially at C), Michael Busch, Riley Greene, Seiya Suzuki, and Brandon Lowe (when he’s healthy). But this might be a good year to try to sell high on Lowe and Suzuki.
Focusing on hitters who can give you good OBPs will be important. You could push a bunch a chips (Made, Walcott will definitely be part of that) in to see if you can get Judge or Soto, but here are some players who would draw my interest by position and might be a little cheaper:
3B: Carlos Correa, Caleb Durbin (sneaky SBs), Manny Machado (going to cost you, but blueprint for what you want)
OF: Jurickson Profar, Wyatt Langford (thinking he has a big bounceback), Alec Burleson, Taylor Ward, Mike Yastrzemski, Oneil Cruz (not exactly a help at OBP, but he’s not Mendoza-line bad and steals bases)
SS: Jeremy Pena, Willy Adames, Mookie Betts (I think he could rebound as he played thru whatever illness cause him to lose his power before the Japan series)
2B: Brendan Donovan, Jose Altuve
RULE 5 DRAFT CUTS
Before the FYPD, the teams create a 35-player protected list of their major league and minor league players. During the season the rosters will have 28 MLB players and 25 MiLB players, so this is a chance to add your favorite sleeper or pillage teams with too much depth at a particular position.
With the hole at 3B, this could be a solution if he can’t work a trade. Or a short-term fix at SP, maybe an older arm who still gets solid K/9 output is sitting out there like a Joe Musgrove.
The sacrifice for each player is the lowest remaining draft pick. For Colin’s team, he has two firsts and a 3rd for the 3-round draft. So adding one player from another team would cost a 3rd round pick (11th overall).
TRADES
Here are some interesting possible trades that fit the desire to improve the 2026 outcome (finished 10th in 2025 after getting to 4th at the All-Star Break), while keeping the players young enough to grow with the impressive prospects.
Trade Brandon Lowe and Nick Morabito for Jeremy Pena and Caleb Durbin.
Lowe is flying off Fantrax boards at pick 64 and Morabito was one of the hot-hitting Arizona Fall League prospects. Pena, despite a great season, is still hanging on in the drafts until 128 and Durbin, one of the stars of the 2024 AFL season, fills the need at 3B. This is a good sell high scenario for Lowe, while also improving the SS role in the short term as you wait for Jesus Made.
Trade Seiya Suzuki and George Lombard Jr. OR Bryce Rainer for Edwin Uceta, Jeremiah Estrada and Kerry Carpenter
I think building a strong bullpen will be important to improving this team in the standings. I really like these two young (both 27) arms. Suzuki is coming off a great season. If the Carpenter owner is tired of him constantly being limited to 2-3 at bats for lefty vs. lefty situations or being benched altogether, they may be ready for something much more reliable. The ADP difference for Suzuki and Carpenter is about 135 spots at Fantrax. I would rather move Lombard than Rainer at this time.
FIRST YEAR PLAYER DRAFT
This will be a better than average season for selecting power college arms. The only question is whether one makes it to the second half of the first round, where Colin has two picks. As a Red Sox fan, Colin was a big fan of Jon Lester and got to see him up close at Fenway Park when a seemingly too-good-to-be-true ticket scalper opportunity turned out to be right on the mark.
That said, I think Colin would be excited to see former Florida State lefty Jaime Arnold, who’s fastball sits around 92-94 just like Lester, sitting there when he picks.
If somehow Andrew Fischer or Ethan Conrad slip through, either one of those potential power bats would be very interesting additions to this team’s group of prospects.
I’ll have more on this series coming soon.