John Siebels
Kansas City Royals
Nick Pivetta to White Sox: Had Pivetta replicated his 2025 performance the Padres would have undoubtedly picked up his option for the 2027 season. Instead, he lost the majority of the season to an elbow injury, which also likely damaged his prospects on the free agent market. Luckily, I think the White Sox could be a great fit for the former Cy Young candidate on a short term contract. The White Sox starting rotation, or lack of, was on full display in the ALDS. Pivetta could provide depth and veteran leadership to a young pitching staff on a team that is hungry to prove themselves as more than a one-year wonder.
Adrian Morejon to the Royals: The Royals bullpen was flat out awful in 2026, ranking near the bottom of the MLB in virtually every team category. Before the team could even begin to dream about a return to the Postseason, a complete overhaul of the position group would be necessary, including a high leverage arm and a closer. Going back to 2024 there have been few late inning arms better than Morejon, who is more than due for a shot at a full-time closer role. The Royals blew 26 saves in 2026 and boasted a league worst 6.65 9th inning ERA. Morejon would fix both of those issues and would be the foundation of what could be a fairly strong relief core.
Caleb Williams
Boston Red Sox
Randy Arozarena to the Phillies: Of Caleb’s picks I think this one makes more sense. The Phillies know that their core guys like Harper, Schwarber and Turner are on the tail end of their prime. Signing a veteran like Arozarena wouldn’t require a long contract that could jeopardize their future plans, and would fill their immediate need of a corner outfielder. The market for corner outfielders isn’t especially deep so I would guarantee that Philadelphia is deeply in the mix here.
Seiya Suzuki to the Red Sox: This seems to be a popular pick, but it is one that I strongly disagree with. Suzuki certainly wouldn’t supplant multi-time Gold Glove winner Wilyer Abreu as the everyday right fielder, and would likely clash with Roman Anthony’s role at both LF and DH. On the other hand, if the team had a plan to fit Suzuki into the lineup everyday he would fill their need for a right-handed power bat. Personally I would expect Boston’s biggest splash to be another starting pitcher to elevate an already very strong rotation.
Serafino Diaz
Chicago Cubs
Tarik Skubal to the Mets: Not the most original choice here, but still an important one to discuss. The Mets already have a massive payroll with both Lindor and Soto tied to long term contracts. With the upcoming bargaining possibly putting a salary cap in place it’s possible that some teams will shy away from signing mega-deals like the one Skubal is likely after. Still, this does seem like the logical landing spot with the Mets desperately in need of starting rotation help, and a willingness to spend seemingly unlimited money in free agency.
Freddy Peralta to the Cubs: Once again another popular prediction, and one that I genuinely like.The Cubs have both Clay Holmes and Shota Imanaga hitting free agency and are likely to be in search of multiple high caliber starting pitchers. Peralta fits the role of a veteran to lead the staff, and having quite a bit of playoff experience will be appealing to a team looking to contend in 2027.
Alex Boyajian
Boston Red Sox
Kris Bubic to the Reds: It was only two season ago that Kris Bubic was an All-Star as a member of the Kansas City Royals. Since then, he has spent more time on the IL than he has on the mound and was moved to the Dodgers at the 2026 deadline. Bubic has shown the ability to have success as a starter and out of the bullpen and that kind of flexibility could be beneficial to the Reds, who are projected to be moving multiple key pieces this offseason. Bubic hasn’t shown the ability to stay healthy with the workload of a starter, but an affordable long-reliver who can be trusted for an occasional spot start is valuable to a team likely entering a rebuild.
Nick Martinez to the Red Sox: Going back to my take on Caleb's picks, I believe the Red Sox are best served by shoring up the back end of their starting rotation before attacking their needs offensively. It is entirely possible that the Red Sox bring back Sonny Gray in free agency, and if so Martinez would likely slot in as their #4 starter and would make this rotation one of the deepest in baseball. At 36 years old it is unlikely that Martinez would be seeking (or being offered) anything more than a two-year contract, meaning this would be a fairly low-risk, high-reward signing for the Red Sox as they look to compete in a perpetually challenging AL East.
John Siebels is the owner of Springhill Sports Cards, he collects and sells sports cards on Whatnot, you can find him on TikTok, YouTube, and his Whatnot store.
