Deep Dive into the Yankees’ and Other Teams’ Strategies in the Offseason
Is New York Yankees [General Manager](/mlb/team/_/name/nyy/new-york-yankees) Brian Cashman a wise strategist, an inadequate messenger, or something completely different? The answer to this question arises from the analysis of the decisions made by the team in the offseason and their impact on the future. The press conference at the end of January, where Cashman expressed his enthusiasm for “running it back with those guys”, sparked debate among fans. This statement, which defended the team’s approach in the offseason, generated controversy due to the lack of renewal of the squad, which remained similar to that of the previous season. Let’s analyze the 2025-26 offseason using Cashman’s words as a guide. How do we classify a team’s approach in the offseason? What strategies are most effective, considering the team’s position in the competition cycle? To simplify the analysis, we divide the teams into three categories: good, average, and bad, based on their performance from the previous season. For each category, we identify six types of offseasons, considering aggressiveness in free agency and trades. Next, we will explore what we can expect in 2026.Already Good Teams
Passive Low Season with a Great Signing
Description: We are contenders and we like our team in all positions. However, we do not rule out an elite free agent, whether from a competitor or one of our own that we want to keep. We are good. We are going to “run it back”.2026 Teams: [Chicago Cubs](/mlb/team/_/name/chc/chicago-cubs), [Detroit Tigers](/mlb/team/_/name/det/detroit-tigers), [Los Angeles Dodgers](/mlb/team/_/name/lad/los-angeles-dodgers), [New York Yankees](/mlb/team/_/name/nyy/new-york-yankees), [Philadelphia Phillies](/mlb/team/_/name/phi/philadelphia-phillies)Meaning: The Yankees were classified as passive due to their continuity score. Although the team is projected to be very good, most of the activity during the winter focused on maintaining a similar roster. The team has evolved, and that process will continue even after the offseason ends. The Yankees’ continuity score at the beginning of the previous season (69%) indicates considerable turnover, especially for a contending team. The Phillies and Yankees had similar offseasons, with significant retention of the end-of-season roster and dedicating much of their effort (and spending) to keeping the same group. The difference lies in the long-term trajectory. The Phillies (78%) outperform the Guardians (71%) in terms of three-year continuity scores. The Yankees (64%) are in the lower half of this measure. Cashman’s strategy, in the long term, has involved active roster iteration, something that has not been as evident in the Phillies, whose window of opportunity appears to be shrinking.Numbers: In general, bad teams tend to improve a bit the following season, while good teams tend to get slightly worse. Teams in the middle tend to stay in the middle. In the free agency era, 4% of teams end up in this category, averaging a loss of 2.4 wins the following season. Six have won titles, including three Yankees teams (1978, 1999, 2000). Passivity is often a characteristic, not a mistake, when you are already good.Passive Low Season Without a Big Signing
Description: This is the group that stands firm. Good and trusting in the same as a similar template.2026 Teams: [Milwaukee Brewers](/mlb/team/_/name/mil/milwaukee-brewers), [Seattle Mariners](/mlb/team/_/name/sea/seattle-mariners), [Toronto Blue Jays](/mlb/team/_/name/tor/toronto-blue-jays)Meaning: These were the three teams closest to the 2025 title without winning it. All are trying to take the final step with small adjustments. The Brewers, who negotiated with starting pitcher [Freddy Peralta](https://www.espn.com/mlb/player/_/id/39825/freddy-peralta), were the most active of the three, but will mostly run it back in 2026. The Blue Jays don’t get credit for a flashy signing for the signing of [Kazuma Okamoto](https://www.espn.com/mlb/player/_/id/5134636/kazuma-okamoto), who doesn’t yet have an MLB track record, and [Dylan Cease](https://www.espn.com/mlb/player/_/id/34943/dylan-cease) doesn’t qualify, but the Blue Jays aren’t that different overall. The same goes for the Mariners, who are usually aggressive and were very specific in their offseason work.Numbers: 12% of teams fall into this category, suggesting a tendency for good teams to rest on their laurels. These teams lose an average of 4.8 additional games the following season, the second-smallest amount of regression at the good level. Therefore, teams that really want to let it ride are often justified in making that decision.
Low Season Active Without a Big Signing
Description: We’re good, but, what the heck, we’re going to revamp the roster anyway. We don’t need to reach free agency star level, but there will be many new faces in our locker room.2026 Team: [Boston Red Sox](/mlb/team/_/name/bos/boston-red-sox)
Meaning: Historically, there are many demolition teams in this group. In other words, they are recorded with a low continuity score not because they are betting everything, but because they are waving the white flag, probably for economic reasons, as they say.
Which brings us to the 2026 Red Sox. The non-big-signing part of the descriptor is a barely-there trait; despite the signing of [Ranger Suarez](https://www.espn.com/mlb/player/_/id/39817/ranger-suarez), Boston is just below the bar for a signing. The Red Sox were also active in trades, which doesn’t fall into the signing classification, although it’s there in the active/passive dichotomy.Numbers: A solid sample of 5% of the teams since 1977 are in this leaky group. They have lost an average of 10.9 wins from one season to the next, by far the largest of our 18 groups. None have won titles.Moderate Off-Season Without a Big Signing
Description: The template is mostly solid after last year’s solid performance. So we’re plugging holes, but without worrying about elite free agents and the contracts they’ll demand.2026 Teams: [San Diego Padres](/mlb/team/_/name/sd/san-diego-padres), [Texas Rangers](/mlb/team/_/name/tex/texas-rangers)
Meaning: The Padres, typically manic, played it a bit calmer this winter, possibly due to budget constraints. Moves were made, but none of them were at a star level. The Rangers are an interesting group. Texas has a different look from an offensive style perspective and a new manager in Skip Schumaker. But the overall rotation wasn’t that strong and the Rangers didn’t spend much in free agency.Numbers: 7% of teams finish here and lose an average of 6.7 wins the following season. Five of them have won titles, including the 1977 Yankees. The most recent were the 2021 Braves.
