Tim Kester played minor-league baseball for 13 seasons, between 1993-2007, in the Houston, Boston, and Baltimore organizations. A right-handed pitcher who made 423 professional appearances, Kester also spent several seasons playing winter ball in Latin America, which he talks about in this essay.


The casual baseball fan is probably curious about winter ball, what it is, and why American players would leave the comforts of an offseason at home to go play. Here's a rundown of the basics of playing winter ball from a player's perspective along with a few stories.

Winter ball is played in Venezuela, Mexico, the Dominican Republic, and Puerto Rico. With the exception of Mexico, it is the only time of year professional baseball is played in those countries, so the fans and native players treat it like it is their major leagues. At the end of the season, the champions of each league play each other in the Caribbean Series. This is a huge deal to both the people in these countries and the players because all four of these nations believe it is the dominant force in Latin American baseball. Many established major-league players who are citizens of these countries will play the last month of winter ball just to be able to represent their nations in the Caribbean Series. It really is a testament to how important winter ball is to these countries that an established major-leaguer would play an entire major-league season and then play winter ball for little pay just to represent their countries.

Winter-ball teams usually have a working agreement with one or more major-league teams. MLB teams will send minor-league players and coaches to help teams, which also makes it easier to scout up-and-coming talent from those countries as well as American players playing in Latin America. The American coaches usually try to look out for their players by making sure they aren't overused or hurt, among other things.

There are a couple types of American players that end up playing winter ball. The first is the young prospect who needs more work because he didn't get a full season in the minors or just needs a little more experience. A guy who was injured or coming off of surgery that needs to get some more playing time is a good example. Teams tend not to send guys that are too young because the environment can be a little intense. There is a lot of pressure to perform, and the teams want to win and win now. It's a great learning experience because in the minors it's all about developing players, and winning is secondary, but winter ball is just like the big leagues in that the bottom line is winning.

Before my first start in Venezuela I was assured by my pitching coach that I would throw between 30-35 pitches because I hadn't pitched in a game in a couple months. In the fifth inning he came to the mound and asked how I felt. I asked him how many pitches I had and he said "only 65." I asked him what happened to the 35? He just shrugged his shoulders and said "we're trying to win." The competitor in me said I was OK and I finished the inning.

That happened because I was the second type of player that goes to play winter ball; the minor-league free agent who is looking to make some money while being seen by scouts from major-league clubs and, hopefully, impressing someone enough to get a contract for the next summer. That type of player usually gets treated a little differently because they don't really have a major-league organization looking out for their best interests like the young prospects. You're just a hired gun who's there to put up or get out. Once you understand that and realize that you are the only one looking out for your best interest, even if sometimes you may have to pull yourself out of the game, the better off you are. It took me all of one start to learn that.

Besides making some money and sharpening your skills as a baseball player, winter ball can be a great teacher of life lessons and a real eye-opener for most American players in terms of seeing how not just baseball, but life, is different in these Latin American countries. I remember the first night going out to a nightclub in Puerta La Cruz, Venezuela. We walked outside the bar at around 4 a.m. to see five people (three guys and two girls) in a serious fist fight, complete with broken bottles like something out of a movie. A security guard saw this and casually strolled over, pulled out his gun, and fired five shots in the air to try to break up the fight. The fighters didn't even flinch! Not until another guard came out and blasted a shotgun into the air did they scatter. Another American player and I witnessed this in disbelief from behind a wall about 50 yards away. I mean, seriously, you won't see that in Cedar Rapids, Iowa. You won't even see that in Detroit! Well, maybe Detroit.

Most people know that baseball players like to play practical jokes on each other, especially on long road trips where there is a lot of downtime. One day on a long bus trip, a Venezuelan player fell asleep with his mouth open, usually a bad idea with a group of baseball players. In Venezuela, where most players carry guns for personal protection, it is the worst idea ever. One of the Venezuelan players thought it would be funny to take the bullets out of his revolver and put it into the sleeping guy's mouth with the hammer cocked back. As the entire team gathered around, they woke him up. To say the least, the guy was a little surprised. I've never seen anyone go from a dead sleep to eyes opened as wide as his. Imagine if one second you're dreaming of painting the corner with a knee-high fastball and the next you're looking down the barrel of a gun with the hammer cocked back. To top it off, a second after he opened his eyes the guy holding the gun pulled the trigger and the hammer on the empty gun went 'click.' The entire bus of Venezuelan ballplayers erupted into laughter. I have to admit, in a sick demented kind of way, it was a little bit funny. The next day our team's general manager had a meeting and told the Venezuelans to stop playing around with their guns because the Americans were freaking out and might go home. Needless to say, none of us fell asleep on the bus for the rest of the season.

Just like any major U.S. city, as long as you use common sense, it's not as dangerous as you might think. The most dangerous situation I was during my time in Venezuela actually happened on the field. We were playing a day game against the Leones in Caracas and Jose Castillo, who was with the Pirates at the time, hit a walk-off home run the night before to beat us. He must have done 10 minutes of curtain calls and hamming it up afterward. He happened to be the leadoff batter that day and I accidently drilled him in the elbow with the first pitch of the game. He went down like he was shot and rolled around on the ground while the 20,000 angry Venezuelans chanted in unison "SUSIO… SUSIO… SUSIO"…, which means 'dirty' in Spanish. I guess they were talking about me. I don't know why, because it was clearly an accident. No, really, it was. I think they may have also been saying some uncomplimentary things about my mother. I'm just glad my Spanish is no bueno. Beer bottles and other debris started to rain down onto the field and we had to retreat to the dugout until the mayhem stopped and the grounds crew got the field cleaned up. I wondered if I would leave the stadium alive if I accidentally hit another guy.

Overall, playing baseball in Latin America was an awesome experience that I wouldn't trade for anything. The enthusiasm the people in those places have for the game is second to none.

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WOW! That's some good stuff! They definitely take their baseball serious down there
Thanks for sharing this...awesome article!
Very interesting, thanks!
Thanks, Tim! Great stuff...
thanks, this was an enjoyable read.
Nice to have the personal perspective on it, thanks for sharing that with all of us.
Thank you for 'accidentally' writing this article...very entertaining.
Great perspective. Thanks for sharing.
Boys will be boys, eh? Only in Venezuela is putting a gun in someone's mouth--loaded or unloaded--supposed to be funny. I guess in America the jokester might suddenly get his grill re-shaped a little, All in all, though, a nice glimpse of life in Central America.
Very cool.