Five Mocks Trades That Would Make Both Teams Better

With a weaker free agent class than usual, the MLB trade market is going to be rampant this winter. Here are some deal that help both sides.

Tyler Glasnow
CLEVELAND, OH - OCTOBER 8, 2022: Tyler Glasnow #20 of the Tampa Bay Rays throws a pitch during the fourth inning of game 2 of the wild card series against the Cleveland Guardians at Progressive Field on October 8, 2022 in Cleveland, Ohio. (Photo by George Kubas/Diamond Images via Getty Images)

The offseason has started fairly slow to this point, but that is not going to last for long. With the Winer Meetings on the horizon, the free agent and trade market will get hot soon.

With a free agent class featuring some high-end pitchers, a few impact bats, and a generally thin group of position players. With a handful of teams in need of a retool, many of the major moves this winter could occur via the trade market.

As we looked into the possibilities, I decided it would be fascinating to create a few trades that I could envision benefitting both sides. In some cases that means a deal that helps each team win in 2024 while in others it adds to one team while helping another build for the future.

Let’s dive into five deals centered around some of the biggest names who could be on the move. While the trade package could differ significantly for some, I think that the teams referenced in these deals are perfect trade partners for various reasons given the goal of each team.

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Baltimore and Guardians Fill Needs

Orioles Acquire: RHP Shane Bieber

Guardians Acquire: OF Anthony Santander

After falling well short and getting swept in the first round of the playoffs, the Orioles have one mission this offseason: Find starting pitchers.

They won 101 games in the first of what will be many contending years for the best young team in baseball, which still has ample minor-league talent. While the Orioles will have plenty of chances to finally part with prospects in exchange for pitching, this deal gives them the opportunity to trade from a source of strength in exchange for a proven starter.

Shane Bieber comes with injury concerns and his stuff ticked down to a degree this past season in which he made just 21 starts. This past season was likely the worst of his career since his rookie year as he finished with a 3.80 ERA and by far a career-low strikeout rate of 20.1% across 128 frames.

With Kyle Bradish breaking out and Grayson Rodriguez showing his promise, Bieber would form a strong trio at the top of the Baltimore rotation. His experience would be invaluable but the Orioles would only gain control for one season.

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The Guardians have ample depth of young pitchers led by the likes of Tanner Bibee and Gavin Williams but absolutely need to add power to their offense. With Baltimore having too many position players to start every day, they could consider moving a veteran outfielder such as Santander or Austin Hays.

Cleveland would likely prefer Santander and he may be the best singular player that they could add to their lineup in exchange for one year of Bieber. The veteran outfielder has 61 home runs across the past two seasons with a wRC+ of 122 and 119 in each year respectively.

It feels like a rare one-for-one swap of Major League pieces that could benefit both teams, similar to the Pablo Lopez for Luis Arraez trade from last year.

Braves Get Their Arm

Braves Acquire: RHP Tyler Glasnow

Rays Acquire: RHP JR Ritchie and RHP Spencer Schwellenbach

Despite being a 99-win team in 2023, the Rays are perenially looking to reduce costs and build from within their farm system. It has been well-documented that the team is considering moving Tyler Glasnow given the sharp rise in his contract value for the 2024 season prior to him hitting free agency next year.

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Meanwhile, the Braves fell short again in October to the Phillies despite being the best team in baseball throughout the entire regular season. They’re clearly involved in the starting pitching market with a desire to add another elite starter alongside Max Fried and Spencer Strider at the top of their rotation.

The Braves may be hesitant to deal out long-term money in comparison to other teams pursuing the top pitchers on the market, which could lead to them trading for the Rays’ veteran ace.

Glasnow comes with a serious injury history but has proven himself to be effective when on the mound. In 37 starts across the past three seasons, Glasnow has a 3.10 ERA, 2.86 FIP, and over 12 strikeouts per nine innings pitched.

For Tampa, turning a proven starter into two young pitchers with stuff to succeed is on par. Schwellenbach has a strong three-pitch mix and has clear starter upside despite minimal innings under his belt. Ritchie is a pitcher with advanced secondary offerings at this stage who can continue to develop within the Rays’ pitching system at just 20 years old.

Atlanta would secure their top-end starter with the Rays cutting costs and adding a pair of young arms to their system.

Brewers and White Sox Buy Low

Brewers Acquire: DH Eloy Jiménez

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White Sox Acquire: LHP Aaron Ashby and INF Juan Baez

Two teams with a need to establish their direction this winter could benefit from swapping two players who are currently at a low point in terms of value.

The White Sox are entering a “retooling” season in which they are poised to move on from their former core in hopes of preparing for future contention. It seems as though Eloy Jiménez is a prime trade candidate for Chicago given his lack of availability in the past few years in addition to him being solely a designated hitter at this point.

Milwaukee is in desperate need of power within their lineup as they continue to fall short at the plate in the postseason. Jiménez when at his best would become one of the best hitters in the Brewers’ lineup. They don’t have a clear DH right now which gives him a spot to slot into immediately for up to three seasons after he signed a large extension with Chicago a few years back.

After a promising full rookie season as a swingman in 2022, Aaron Ashby missed most of 2023 with a shoulder injury and struggled in his minor-league rehab starts down the stretch. Command has continued to be an issue for him but he is still just 25 years old and the White Sox are in desperate need of young starting pitchers. Due to what Jiménez has shown at the big league level previously, I think a flier heading back to Chicago alongside Ashby makes sense.

This deal would be complex for a number of reasons with neither team wanting to sell low on a formerly highly-regarded asset, but I can see how it would help both sides.

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Giants Get a Center Fielder

Giants Acquire: CF Dylan Carlson

Cardinals Acquire: RHP Mason Black and RHP Landen Roupp

It’s no secret that St. Louis wildly underachieved last season, finishing last in the NL Central after winning the division in 2022. They have a deep core of outfielders without clear playing time for all of them. It feels like Dylan Carlson could be the odd man out after a poor 2023 season which saw his numbers at the plate drop well below his career marks.

He finished his first full season in 2021 with a 111 wRC+ while playing elite defense at just 22 years old. He dropped down to a 99 mark in 2022 before falling all the way to 84 last year. Carlson is a great defender in center field and should be on the radar of many teams in need of a center field with upside.

The Giants are seemingly intending to compete and are going to be bidding for many of the top names available this winter. With a hole in the outfield, specifically in center, they seem like a good fit to bring in Carlson’s elite glove and bat that could be much better. He has produced well against left-handers consistently which could lead to him being a platoon in San Francisco at the least.

Meanwhile, the Cardinals are looking to add league-ready pitching as they have continued to struggle to find arms to put together solid innings. Mason Black is a top-10 prospect within the Giants’ farm system and reached Triple-A last year. He struggled in his first taste at the highest minor league level with an elevated walk rate.

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However, he is near league-ready and flashed high whiff rates with unlucky batted ball data against him while pitching in a hitter-friendly league.

Landon Roupp is seemingly a reliever at the next level but was dominant in Double-A and is older for his draft class which could lead to him debuting in 2024.

Red Sox Solidify Infield

Red Sox Acquire: 2B/INF Jorge Polanco

Twins Acquire: RHP Kutter Crawford and 1B Bobby Dalbec

Boston finished last in the best division in baseball last year but they appear ready to improve right now. With Triston Casas emerging as a star at the opposite corner to Rafael Devers, the Red Sox are set at the corners for many years.

Trevor Story missed much of 2023 but is set to be the shortstop for at least the short-term future and he could move to second base eventually.

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This leaves second base as the one obvious hole in the Boston lineup. They need several pitchers but could acquire another lineup starter via a trade that costs them minimal assets. The Twins are set to reduce their payroll this season and that could lead to Jorge Polanco being on the way out with both Royce Lewis and Edouard Julien capable of taking over at second base.

With a club option for 2025, the Red Sox could add an infielder who could start at second and play shortstop or third base for them when needed as well.

Minnesota has options to fill Polanco’s role and they are expecting top prospect Brooks Lee to make an impact in the near future. They could save money with this move and acquire a pitcher who could fill out their rotation in Kutter Crawford. He was available all season for Boston and pitched to a 4.04 ERA with a 1.11 WHIP and would be a great back-of-the-rotation piece for Minnesota.

Bobby Dalbec’s career with the Red Sox has not gone as expected but he could be given a chance to display his power in a lineup seeking right-handed power. This deal probably helps Boston more than Minnesota in the short-term, but given the depth of the Twins’ infield, Crawford would be a great get for them.