The Brewers-Rays World Series is set to put an old Guardians deal back under the microscope.
Back on Dec. 13, 2018, Cleveland brought Carlos Santana back as part of a three-team trade with the Mariners and Rays, a swap that wound up creating one of the messier trade trees in recent memory.
For a while, it looked like the Guardians might have come out on the wrong end of it. Yandy Díaz, one of the players they sent away, developed into an All-Star with Tampa Bay, while Santana turned in a strong 2019 season for Cleveland.
The move also helped the Guardians get out from under Edwin Encarnacion’s contract.
Now that balance is about to shift again. Later this week, Milwaukee and Tampa Bay will meet in the World Series, and no matter what happens, one piece from that 2018 trade is going home with a ring.
On one side is Díaz, who earned his second career All-Star nod this season and then played a huge role in knocking the Guardians out in the ALCS. On the other is Jake Bauers, the player Cleveland received in the deal, who never found his footing with the Guardians.
Bauers’ path has been the stranger one. He struggled after leaving Cleveland, bouncing through the Mariners and Yankees before the Brewers cut him loose ahead of last season.
Then came the turnaround. He put together a career year for Milwaukee in the regular season, and he followed it with the best series of his life in the NLCS, good enough to earn MVP honors.
JAKE BAUERS PUTS THE BREWERS BACK IN FRONT! pic.twitter.com/KK8xCFd7j1
- MLB (@MLB) October 15, 2026
Cleveland did see flashes from Bauers, but not enough to keep him on the roster, and he was let go after a rough start to 2021.
Díaz’s story took a very different route. He came up in the Guardians’ system, but with José Ramírez holding down third base, Cleveland never really had room for him. The Rays made immediate use of him, turning him into a productive first baseman almost right away.
Since then, he has hovered around a .300 batting average in every season but one in Florida and grown into a central figure in the Rays’ lineup. He’ll be right in the middle of it again during the Fall Classic.
The matchup was already going to be an uncomfortable one for Guardians fans because it features two small-market teams, including the one that bounced them from the postseason. With Díaz and Bauers both playing key roles, the sting only figures to get sharper.
There’s still an argument that Cleveland was justified in moving on from both players. That won’t make this World Series any easier to watch.
In Other News...
Steven Kwans Guardians Comments Mean More Than Fans Might Think
Steven Kwans season finished on a far better note than it began, and the broader view matters here as much as the numbers. After a rough first half, he settled in and finished with a strong 114 wRC+, reinforcing why he remains one of the more valuable everyday pieces on the roster. Along the way, he also made clear how he feels about the group around him, praising the Guardians young core and sounding genuinely energized by what the club could become.
Those comments carry extra weight because Kwan is no ordinary talking point for the front office. He is moving toward his contract year in 2027, which puts Cleveland in the familiar position of weighing whether to extend a homegrown player or eventually cash in on his value. For a team built around young, controllable talent, Kwans outlook is a reminder that the Guardians may soon have to decide whether their vision for the future includes one of their most reliable bats for the long haul. [Read more 🡒]
Guardians Near-Miss Put Three Roster Problems Front And Center
A familiar postseason frustration has pushed Cleveland right back into roster-building mode. After falling to Tampa Bay in six games in the American League Championship Series, the Guardians enter the winter with the same basic mandate that has shadowed them for stretches of the season: find more offense and shore up the starting rotation if they want to take the next step.
Those needs also narrow the priorities. Cleveland could use help in the outfield, with Jarren Duran among the names worth tracking, and the rotation has room for another arm such as Michael Detmers. There is also the more obvious hole at first base, where the Guardians still need a reliable everyday answer, and solving even one of those issues would go a long way toward making the lineup and staff fit together better. [Read more 🡒]
Guardians Face A Tough First Base Call After ALCS Run
The Guardians run ended in the American League Championship Series, and the next phase of the offseason is already starting to come into focus. Along with the usual list of contract decisions, Cleveland has a few familiar names headed toward free agency, including Nathaniel Lowe, Austin Hedges, Rhys Hoskins and Foster Griffin, while Shawn Armstrongs situation sits in the middle with a mutual option to sort through.
First base is one of the more interesting calls on the board. Cleveland has to decide whether to keep Lowe in the mix or let him walk, and the answer could shape how quickly a younger option gets a real look. Ralphy Velazquez is among the prospects the organization is weighing for future contributions, which makes this a position to watch as the Guardians try to turn an encouraging playoff finish into a more settled roster plan. [Read more 🡒]