Since then, the only other team representing Puerto Rico to win the Caribbean Series was the Cangrejeros de Santurce, in the Dominican Republic in 2000. The MVP of that series, Jose Cruz Jr., reflected recently on what that meant to him and the group representing the island that year.
"That Caribbean Series was extremely special," said Cruz, who hit .385 with five doubles, eight runs and 10 RBIs to help Puerto Rico go undefeated in its six games. "It was all about the team and country."
With a lineup that featured such big leaguers as Cruz, Jose Vidro, Jose Valentin, Armando Rios and Eduardo Perez -- who is managing the Santurce team representing Puerto Rico in the 2015 series -- the Cangrejeros (Crabbers) set records for hits (86), doubles (24) and team batting average (.365).
"Everybody was hot," said Cruz, who hit 204 home runs in a 12-year Major League career from 1997 to 2008 and is now in the player services department of the MLB Players Association. "It was well deserved, I thought. I thought we were definitely the best team that year."
In addition to the success on the field during that first week of February 2000 in Santo Domingo's Quisqueya Stadium, what stands out for Cruz was the closeness of that team for those few days.
"We had the best time," he said. "We as a team got along great. The bus rides to the stadium were hilarious. Then when everybody got to the field, they did their thing, enjoyed it and it really wasn't so much of a job. Everyone was pulling for each other.
"It was a great moment, not only for my team but for my country."
Since that win in the 2000 Caribbean Series, Puerto Rico has seen its share of hard times in local baseball. For the winter league, it's been a slow but steady process to emerge from the abyss of cancelling an entire season seven years ago, when playing it out was deemed financially unfeasible.
"Puerto Rico went through a lull there for a bit. It's definitely concerning," said Cruz, son of local legend and former Houston Astros standout Jose Cruz Sr. "It's something that we're working on, trying to promote baseball and spark that fire again. The island loves the game, so now it's about getting the youth back involved in it."
Cruz believes a good showing by Santurce as the host club at this year's Caribbean Series -- which will also include Tomateros de Culiacan (Mexico), Gigantes del Cibao (Dominican Republic), Caribes de Anzoategui (Venezuela) and Pinar del Rio (Cuba) -- could go a long way toward achieving that goal.
"If we could get to the final and hopefully pull it out in our homeland, our home park, it would work wonders, I think, for amateur Puerto Rican baseball players for years to come."
In 2015, enthusiasm for the present will be combined with celebrating the 1995 Puerto Rican team, the Senadores de San Juan, whose members will be honored on Tuesday between games of the scheduled doubleheader.
Composed of Roberto Alomar, Baerga, Carlos Delgado, Bernie Williams, Edgar Martinez, Ruben Sierra and Juan Gonzalez -- among other renowned big leaguers -- that squad earned the nickname "Dream Team" while easily winning its six games in San Juan.
At the time, Cruz was just a few months away from being selected in the First-Year Player Draft by the Seattle Mariners.
"I remember that team. I was so excited to see all those guys on that team," Cruz said. "They were such icons, especially when I was growing up.
"These were the guys I was looking up to, that I wanted to play with, play against and play like. What a team."