The Chicago Cubs have learned the benefits of signing players to one-year deals. While those don't always work out, there have been some recent examples around Major League Baseball that have.
There will be multiple players on the market who could get a similar deal this winter, and if the Cubs don't feel comfortable giving said player a long-term deal, smaller contracts could be the best solution.
Regarding Chicago's free agency, they should be in the mix for some of the top players on the market. More often than not, those types of guys get long-term deals.
However, Steve Henson of the Los Angeles Times doesn't expect that to be the case with one of their targets.
Henson highlighted that outfielder Anthony Santander could benefit from taking a short deal with high average annual value, potentially upping his price the following offseason.
"A legitimate power hitter who strikes out a ton, doesn’t walk a ton and doesn’t hit for average, Santander is coming off a career year. He had 44 home runs and 102 RBIs with the Orioles and entered a market thin on corner outfielders. But he could languish the way Hernández and others did a year ago and end up with a short deal with a high average annual value."
From Santander's perspective, taking a short-term deal wouldn't make the most sense. While he doesn't have all the say in that, as teams like the Cubs would have to give him a deal first, he's 30 years old and is coming off the best campaign of his career.
The switch-hitter finished with 44 home runs, and when players do that, they get paid. If he wanted to test the market in 2026, there's a very good chance his price would be significantly lower.
There's still a scenario where Santander taking a one-year deal could benefit Chicago, however. If they were to sign him to a high AAV deal and spend on others, their lineup could be in a great spot.
Factor that in with him potentially enjoying the city and wanting to re-sign in the following offseason at a lower price than he might be right now, and the Cubs could get a steal.
Free agency is now open, but players can't sign until five days after the World Series. Santander should have suitors, but he's an interesting free-agent name to follow.
If his price isn't where some have predicted, Chicago should be all in on him.
