These teams are in the Dominican Republic, Venezuela, Puerto Rico and Mexico, and they all have one goal in mind: being the last club standing at the Caribbean Series in Hermosillo, Mexico, come February.
It all gets started now, with the Venezuelan League kicking off play on Thursday, Mexico on Saturday and the Dominican on Sunday. Puerto Rico's league doesn't start until the beginning of November.
By the time the Caribbean Series begins, the teams involved will be dotted with Major Leaguers who love representing their home countries in one of the most spirited competitions baseball has to offer. For the next few months, however, Major League teams send many Minor League prospects to experience the unique world of winter league baseball.
"It's another opportunity to compete, to play against good competition in a different type of environment," White Sox assistant director of player development Del Matthews said. "In winter leagues, development is less stressed and competition and winning is more so. It's a great opportunity for our prospects to compete in that environment."
The White Sox are sending four of their Top 20 prospects to various clubs, though two -- No. 7 Carlos Sanchez and No. 18 Andre Rienzo -- won't get to Venezuela until after the Arizona Fall League, with Rienzo being further delayed by Brazil's World Baseball Classic qualifier. Chicago isn't alone, with many teams sending top prospects to the Caribbean to get more experience.
top prospects in caribbean leagues
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"For us, there are several layers to it," said Nationals farm director Doug Harris, who has three Top 20 prospects -- Eury Perez, Zach Walters and Sandy Leon -- playing in three different leagues. "It's an opportunity to pile on repetitions offensively and defensively. They're exposed to a different kind of baseball. Lastly, the intensity is great for all our young men. It's an important part of the developmental process."
Unlike the Fall League, which is more of a laboratory setting where players can work on specific things without the glare of the spotlight or the expectation to win, winter ball is all about winning. These clubs are run independently from Major League Baseball and the 30 clubs. Decisions are made based largely on what gives them the best chance to make it to the Caribbean Series. Just because an organization wants a prospect to work on a certain pitch, or play a certain position doesn't guarantee it will happen. Having a rapport with the winter league clubs is essential to make sure that both sides come away with what they want.
"We've been very fortunate and had very good relations with the clubs our players have been with," Harris said. "It starts with the time they ask for permission. You have to try to establish those parameters and maintain the communication throughout the season. We respect what they're trying to accomplish. As long as we communicate, they understand there are certain parameters that exist."
Matthews echoed that sentiment, talking about finding a balance between development and the win-first mentality in the winter leagues. He's seen it work, pointing to reliever Hector Santiago as an example, and thinks that perhaps the independence of these leagues can actually be more of a benefit than a hindrance.
"A couple of years ago, Hector Santiago developed a screwball in Puerto Rico," Matthews said. "He came to Spring Training and everyone said, 'Wow.' Now he's got a feel for a screwball and he's a different guy for us. It catapulted him a little bit, and he pitched in the big leagues for us.
"The player has to somewhat figure it out for himself. You want them to get to that point, where they can make adjustments on the fly, where they don't always have to go to a coach. Ultimately, that is better for their development."
That being said, it's not for everybody. Especially for an American-born player, making his way through a winter ball season can be a bit treacherous. The transition for Latino players coming to the United States can be tough, but at least there are formalized support systems and time to adjust. In reverse, during winter league play, it's a cultural crash course with the expectation that contributions on the field will be made immediately.
"The important thing is sending the right type of player," Matthews said. "They are in a different country. The living conditions or travel might not be the best, but they have to want to go and know they are going to be able to work on something down there. They need to get something out of it."