Buying at the Trade Deadline

We’re less than a week away from one of the most important dates on the baseball calendar: the trade deadline.

It’s a critical decision point for teams. They’re declaring their intentions for 2026 and making choices that will impact the organization for years to come.

The volume of deals makes the week unlike any other. Although trades are allowed most of the year, the week leading up to the deadline sometimes feels like the only window for swaps. Last year a record 63 trades were completed in the seven days prior to the deadline, up from 59 in 2024.

The draft is a difficult decision environment, but the deadline is something altogether different. In the draft, teams pick a set number of players with an allotted bonus pool over two pre-scheduled days. The deadline doesn’t have any of that certainty.

And while every team faces challenges, the hardest questions are reserved for the buyers. In particular, these three influence every decision facing teams looking to add at the deadline.

The reason that buying is so difficult is the math almost never supports it.

Baseball is a team sport where no individual player makes the same level of impact that stars in other leagues can. The best acquisitions only project to add one or two percentage points to a team’s odds of winning the World Series — maybe a little more than that in the case of multi-player deals like when the Dodgers acquired Max Scherzer and Trea Turner in the same package.

Adding a player for two months and a playoff run rarely justifies the value given up.1 Teams that buy pay a premium to improve in the present, usually trading away two to three times the future value in exchange for the players acquired. And even though the prospects don’t always pan out, it’s devastating when you move a Pete Crow-Armstrong or a Yordan Alvarez for a small, short-term improvement.

That’s why it’s critical for teams to decide how important this season is for them. One thing that can swing the math a bit is applying a discount rate to wins. A discount rate essentially reduces the value of future wins compared to wins in the present year due to time preference, future inflation, and risk.

Reasonable people can argue how much, if any, discount rate should be applied to baseball wins. I’d argue that something is warranted, but it’s not a question that can be answered objectively. Every team has to answer it on their own based on their ownership preferences, competitive window, and, in some cases, job security.

The discount rate typically won’t flip the math in favor of the buyers, and it shouldn’t be gamed to do so, but understanding the value on the present season makes every decision at the deadline a little easier.

One of the least talked about challenges of buying is the limited supply. If a team has a hole to fill, there are only so many options actually available. The more specific the need, the more difficult it will be to find alternatives.2 And the expanded playoff pool only adds to the problem.

What complicates things further is the players teams want to acquire tend to cost the most. Healthy, affordable, and productive players don’t fly under the radar. The competition for them is stiff, and if they have control remaining, they very well may not move at all.

How willing a team is to overpay for a player or check down to a less-heralded option comes down to their conviction in their evaluations.

It’s easy to trust your projections and scouting reports when there’s nothing on the line, but you don’t get to play a trade out a thousand times. You get one outcome, and it can be difficult to give up millions in surplus value — and risk your job — on a player who is underperforming and/or has a limited track record of success. Even if everything tells you they’re going to be good moving forward.

In 2023, we acquired Yusei Kikuchi from Toronto. We projected Kikuchi as one of the best starters available and we felt like we could get more out of him by simplifying his pitch mix. But his actual performance left much to be desired. His ERA was 4.75 and he had been tagged for 16 earned runs over his past three starts. It wasn’t a comfortable decision to trade for him, despite an overwhelming amount of information that said this was the best deal we could make for a starting pitcher.3

I have far more examples of times where we crossed a player off or said no to a deal because we didn’t fully trust our information.4 It happens to every team, and it’s not always wrong.5 There are plenty of times to question information and value certainty. But it’s good to understand that ahead of time because it’s going to impact the number of realistic options and the price needed to improve the roster.

Once a team has figured out how important the season is and gained comfort with their evaluations, attention turns to what they’re hoping to accomplish. That might sound basic, but it’s a step that determines how a team approaches negotiations.

Let’s say a team needs an outfielder and there are three starting-caliber players on the market. If the intent is to come away with one of those players, the best course of action is to rank the players and pursue the top target aggressively. Even if they overpay, that’s a better outcome than trading too much for the last player available. If instead the team wants to upgrade only if the deal is right, they can hold a firm line on all three players and see how things play out.

Establishing intent also helps align actions with messaging. In the American League Central, the top four teams are tightly bunched and no club is over 50% to make the playoffs. What they do at the deadline will change those odds, but it will also signal to their players how much they believe in their chances down the stretch. The vote of confidence may not take up much space in a deal, but it’s worth something — especially in the case of a team like the White Sox that hasn’t competed in recent seasons.

General managers are often chastised for not being disciplined enough at the deadline. Establishing intent matters because it tells you what failures are acceptable in an environment where you’re likely to lose. Discipline only helps if you’re willing to come up empty-handed. Otherwise, it actively works against you. And it’s always best to know that up front rather than figuring it out when it’s too late.

No one ever suggested buying was easy. There’s a lot to consider, and the odds of truly winning a deal are stacked against the buyers. Trades have long tails and, unfortunately, while flags fly forever, they don’t do anything for future seasons.

But — and I can say this from personal experience — buying is much better than the alternative. It means you’re in the playoff hunt, and one thing that’s definitively worse than losing a trade is watching other teams play baseball in October. Teams that find themselves in the enviable position to buy should embrace the opportunity. It doesn’t come along every year.