After attending Colegio Biblico Cristiano High School in San Pedro de Macorís, Offerman signed with the Los Angeles Dodgers as an amateur free agent in 1986. In 1988, he completed his first season of professional play being named as Best Prospect in the Pioneer League. Progressing rapidly through the minor leagues, he made his major league debut against the Montreal Expos on August 19, 1990 becoming the 55th player in major league history to hit a home run in his first major league at-bat.

By 1992, Offerman became the Dodgers’ starting shortstop. On opening day 1993, he was the first batter to ever face the Florida Marlins, striking out against Charlie Hough. He made his first appearance in the All-Star Game in 1995 but was traded to the Kansas City Royals after the season, mostly because of his very poor defense. After a year as a utility player, he won the starting second baseman job in 1997. Offerman had his best offensive seasons in Kansas City, culminating in 1998, when he hit .315 with a league-leading 13 triples and the fifth most stolen bases, 45. After that season, he signed with the Boston Red Sox as a free agent, making the All-Star Game for the second time in 1999.

Known more for his hitting skills than his fielding, Offerman’s offense began to decline in 2000. He was sent to the Seattle Mariners during the 2002 season, but was released afterwards. In 2003, he joined the Montreal Expos in spring training but was cut before the regular season began. He spent the entire year with the Bridgeport Bluefish of the independent Atlantic League. In 2004, he won a spot on the Minnesota Twins roster and led the league in pinch-hits with 12 in 29 attempts. He started 2005 with the Philadelphia Phillies but was released after a slow start. Later, he signed with the New York Mets and was called back up to the majors in June.

He has not played or managed professional baseball in the United States since 2007. On August 14, 2007, while playing for the Long Island Ducks of the Atlantic League of Professional Baseball, Offerman was thrown out of a game against the Bridgeport Bluefish for charging Bluefish pitcher Matt Beech with a bat after he was hit by a pitch. Beech sustained a broken finger in the resulting melee. Bluefish catcher John Nathans was also hit in the back of the head during the bench-clearing melee, receiving a severe concussion that effectively ended his playing career. Beech and Nathans were taken to Bridgeport Hospital where they were treated and released. After being removed from the game, Offerman was arrested by the Bridgeport Police.

On August 15, 2007, he was suspended indefinitely. The independent Atlantic League announced on August 17, 2007 that Offerman would remain suspended at least until the legal case was resolved.

On September 24, 2007, Offerman pleaded not guilty to two second degree assault charges.

His case was pending in Bridgeport Superior Court GA#2 in Bridgeport, Connecticut. He was represented by Attorney Frank J. Riccio II. On October 30, 2007, Offerman was given two years special probation called “Accelerated Rehabilitation (‘AR’).” The Court determined that his actions on August 14, 2007 were of an aberrant nature. The Court also found that Offerman is not likely to offend again in the future.

Most recently, Offerman played in the 2008 Caribbean World Series for the Licey Tigers – Dominican Republic 2 team – where he assisted the team in winning its 10th Caribbean World Series title. During the series he signed a contract with the 2008 Veracruz Red Eagles of the Mexican Summer League.

In December, 2008, Offerman was named player-manager of Licey Tigers of the Dominican Winter League. With Offerman as manager, Licey swept the Dominican Winter League Baseball Championships, winning five straight against the Gigantes del Cibao. As champions, Licey was then invited to participate in the 2009 Caribbean World Series with Offerman as manager (the series was ultimately won by Venezuela). (The Caribbean World Series is affiliated with the Winter League programs of Major League Baseball, featuring MLB players and prospects from the Dominican Winter League, Mexican Pacific League, Puerto Rican Professional Baseball League and Venezuelan Professional Baseball League.)

Nathans filed a $4.8 million civil suit against Offerman in February 2009, claiming that he still has post-concussion syndrome and that the injury allegedly caused by Offerman ended his baseball career. On July 29, 2014, Nathans won his suit, and Offerman was ordered to pay $940,000.

On 16 January 2010, Offerman once again engaged in an on-field assault when he struck an umpire while managing a Dominican Republic winter league game. Offerman, manager of the Licey Tigers, came onto the field during the third inning while losing a 6-0 game to the Cibao Giants, to protest ejection of his catcher for arguing balls and strikes and ended up arguing with first-base umpire D.J. Reyburn. He swung with a right hook at Reyburn, who then fell to the ground. Offerman was detained by stadium security, eventually being transported to the local police station to await the end of the game and Reyburn’s decision whether to ask for charges to be pressed against him or not.

A day after the incident, the American crew that umpired the game resigned their positions with the Dominican Baseball League and left the country, reportedly due to threats and concerns about their own safety. Because of this incident Offerman received a lifetime ban from the Dominican Republic Winter League, a suspension that was eventually lifted in February 2013. Coincidentally, at the time he was suspended, Offerman was replacing Dave Jauss as Licey manager after Jauss was suspended himself for two years for bumping an umpire during a playoff game.

On January 7, 2014, Offerman was again named manager of the Licey Tigers of the Dominican Winter League, replacing Mike Guerrero. With Offerman at the helm, Licey won the Dominican Winter League Baseball Championships, winning five games to three over the Leones del Escogido. As champions again, Licey has been invited to the 2014 Caribbean World Series with Offerman as manager. At present, his team has qualified for the semifinals of the tournament.