Dylan Cease: worst signing of the winter, according to insiders

Right now, there is so much uncertainty surrounding the 2027 season. With teams spending wildly, others unable to keep up, and players having lost their union's executive director, things are in turmoil.

And that could mean a season with fewer than 162 games in 2027.

Currently, there are several owners who are angry that some teams are spending more than others. This creates a gap in Major League Baseball and does not increase the value of franchises.

What's more, the owners of “poor” teams look bad in the eyes of fans.

Is that why the Blue Jays, according to many people in the industry, made the worst signing of the winter in Dylan Cease? Why the Dodgers made the second worst in Kyle Tucker?

According to the people at the Off The Roster podcast, it must be part of the equation.

Are other teams jealous of the Jays signing Dylan Cease?#Cease #BlueJays #SpringTraining @Brandon_N_Wile pic.twitter.com/dASdywkgsj

— Off The Roster (@OffTheRosterPod) February 16, 2026

Note: when we say “worst signing” of the winter, we mean in terms of value for money. We're not just talking about the players, since everyone knows that Cease and Tucker are good players.

But clearly, the industry doesn't think they're worth $30 million long-term and $60 million per year, respectively. And they're not wrong.

But we agree that the Blue Jays and the Dodgers (to name just those two, since the Mets may feel the same way about Bo Bichette) aren't worried about that. They made money by going a long way in the playoffs and they want to reinvest it.

They consider themselves better with these guys than without them… and they know that being cautious in the free agent market doesn't get results. It's a controversial choice, obviously… and it must be a factor in why the Blue Jays are at the top of such a ranking.

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