Five Way Too Early MLB Offseason Predictions

Predictions for where the top free agent arms are going to sign and trades that didn't happen at the deadline, that will this winter.

Blake Snell
PHOENIX, ARIZONA - AUGUST 31: Blake Snell #4 of the San Diego Padres delivers a seventh inning pitch against the Arizona Diamondbacks at Chase Field on August 31, 2021 in Phoenix, Arizona. (Photo by Norm Hall/Getty Images)

While playoff races are heating up and many teams are making their final push, there are some looking ahead to the offseason already. With the longevity of the season, the weaknesses of many teams become evident in August and beyond as players wear down from the season.

With that in mind, I always find it exciting to look into the future and consider moves that could be made in the upcoming offseason.

With a plethora of teams seemingly within or nearing a contention window and the limited free-agent market, we could be in for a complicated offseason. The sellers’ market we witnessed at the trade deadline, especially in the pitching market, may remain constant in the upcoming winter. Furthermore, we could see the limited free agent class sign for rather large deals.

It’s fascinating to consider the possibilities and while most of my ideas likely won’t come to fruition, I like thinking through what types of moves can be made. I’ve got five potentially “bold” predictions but I actually think they make a lot of sense so I’m not going with the “bold” title for now. I’m going to break down the reasoning behind these potential moves. Let’s look ahead to December.

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Marcus Stroman signs three-year, $75 million deal with the Giants

Despite an injury that may hold Stroman out for much of the remaining season, he’s in the midst of one of his career-best campaigns. He’s been one of the best pitchers on the Cubs’ roster this season and will be in for a sizeable payday

While Stroman’s future seems a tad murky right now, you can’t deny an ERA that sat at 3.09 prior to his last two starts made before the injury. He was one of the best pitchers in baseball through the first half of the season and has continued to find ways to be a crafty and competitive pitcher throughout his career.

There was speculation of the Cubs likely trading him before they got hot and ended up buying at the deadline. However, it seems less than likely for him to remain in Chicago after the season.

When looking at potential suitors, many teams are going to be in the market for quality starting pitchers just like we saw at the trade deadline. While more premium targets are available, Stroman is one of the better options with the ability to help anchor the Giants’ rotation alongside Logan Webb.

Dylan Cease Traded to the Dodgers

The White Sox are approaching a whole new era with the front office changes that occurred this week. Whoever takes over the front office, the roster overhaul that began at the deadline and is likely not over yet. The biggest asset by far left on the roster, that could realistically be moved (Luis Robert Jr. isn’t going anywhere), is Dylan Cease.

The team moved a plethora of pitchers leading up to the deadline and has an incredibly thin pitching staff at the Major League level right now, but capitalizing on Cease’s value may still be the best option for the future. They couldn’t find a partner that was able to match their price at the beginning of the month but will have much more time to attempt to do so this winter.

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There was a clear top two in the potential pursuit of Cease at the deadline and I think those two teams remain the same as we look forward to the offseason. The Dodgers have the assets necessary to make a huge move in the winter and their rotation may need further solidifying with injuries all over this year and the potential departure of Julio Urias.

I think the fit and situation make a ton of sense for the White Sox to add a few elite prospects and the Dodgers to utilize their wealth of talent to add another star to their rotation for the foreseeable future.

Blake Snell signs six-year, $175 million deal with the Red Sox

Widely expected to be the worst team in the loaded AL East this season, the Red Sox have exceeded expectations of most this season. While the roster has obvious holes, the team has played well and the offense looks like it’s on track to be a good one for a while. With other teams in the American League only set to improve, the Red Sox need to add pitching this winter to keep up with the rest.

One of the top NL Cy Young candidates is set to become a free agent and will be looking for a massive payday coming off the second-best season of his career, despite a slow start. With a 2.73 ERA this year, Blake Snell is quickly becoming a top free agent in this class and will have plenty of teams calling this December.

The Padres are facing a crucial winter where they need to determine their future plans, but Snell may quickly become an afterthought with all the other factors in play in San Diego. The Red Sox are set to be spenders this winter and have a huge need in their rotation. The fit makes too much sense to me and I think Snell returning to the AL East would be fun for everyone.

There are many other teams that make sense for Snell, but this is the cleanest fit from a need and financial standpoint with the Red Sox having very little invested in their rotation aside from Chris Sale.

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Jonathan India Traded to the Mariners

This idea was floated around the deadline and just still makes sense. The Reds have a tricky yet great dilemma with too many young infielders to find playing time for in the future. With Elly De La Cruz, Matt McLain, Christian Encarnacion-Strand, and Noelvi Marte all in the fold for the long-term future, Jonathan India seems like he’s already on his way out.

India has had a rollercoaster first three years in the big leagues up to this point, which started with him winning the NL Rookie of the Year in 2021 with a .835 OPS and 21 home runs. He experienced a major slump in his sophomore season and has found himself somewhere in the middle in 2023, with a .745 OPS and 14 home runs despite missing some time with injury.

Home versus road splits are a tad concerning when considering that India has been so much better at Great American Ballpark, but he’s still a productive everyday player when at his best. The Mariners brought in Kolten Wong to solve their second base spot but that has gone terribly. They added Josh Rojas at the deadline, but he’s not likely a stable starter for the future.

Currently one of the hottest teams in baseball, Seattle will definitely look to add more this winter as they’re clearly in the middle of contention window. India would be a relatively low-cost addition to their lineup and would fill a hole in the roster.

Aaron Nola signs six-year, $145 million deal with the Arizona Diamondbacks

This is likely the boldest idea in this piece, so I left it for last. While the Phillies are clearly contenders right now and will continue to be so with their current core, I’m not sure they’re going to spend enough to retain their co-ace. Nola is having a down year right now but has been one of the steadiest arms in baseball in the past few years.

He’s set to receive potentially his last major payday this winter and as mentioned prior the starting pitching market will be hot. I expect numerous teams to be in the race for Nola, but I think this is the winter we see the Diamondbacks truly take another step forward. Their offense and farm system set them up excellently for the future, but they need more pitching behind ace Zac Gallen and Merrill Kelly. Insert Aaron Nola.

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The Diamondbacks can probably attain Nola for less than he would have gotten prior to this season but they have ample money needed to make it happen. With very little money allocated to their pitching, Nola would make a ton of sense to slot in between Gallen and Kelly as Arizona prepares to make a deep playoff run in 2024.

I considered other teams to predict Nola to but I can see the fit best with the Diamondbacks. They have the potential to become a scary team with a good offseason this year.