In 1985, Roberto Rivera, a scout for the New York Yankees of Major League Baseball (MLB), discovered Williams and Williams’ friend, Juan González. Though Rivera was not interested in González, who he perceived as not taking the game seriously, he wanted to sign Williams. However, Williams was a few months shy of his 17th birthday, when he would become eligible to sign with an MLB team. The Yankees put Williams in a training camp in Connecticut, near the home of scouting director Doug Melvin. The Yankees officially signed Williams on his 17th birthday.

Bernie married wife Waleska on February 23, 1990. They live in Armonk, New York and have three children: Bernie Jr., Beatriz, and Bianca. On June 14, 2018, Bernie stated he was divorced during an interview on ESPN’s Highly Questionable. One song on Bernie’s 2009 release “Moving Forward” is named after Beatriz (Lullaby for Beatriz). This song is performed by Bernie Williams and his brother, Hiram Williams, on the cello. This song was recorded in Puerto Rico at the Alpha Recording Studios.

Williams managed to break into the majors in 1991 to replace the injured Roberto Kelly for the second half of that season. He batted .238 in 320 at bats. He was demoted to the minors until Danny Tartabull was injured, and Williams earned his stay at center by putting up solid numbers.

In 1995, Steinbrenner again considered trading Williams, this time to the San Francisco Giants for Darren Lewis. The Yankees kept Williams, who had a breakout season. He hit 18 home runs and led the team in runs, hits, total bases and stolen bases. Williams continued his hot hitting into the postseason, leading the Yankees with a .429 batting average in the 1995 American League Division Series (ALDS) against the Seattle Mariners.

After continuing to improve in 1996, Williams again showcased his skills to the baseball world in the postseason. He batted .467 in the ALDS against Texas and played a sparkling center field. He picked up where he left off in the ALCS against Baltimore, belting an 11th-inning walk-off homer in Game 1. Ending with a .474 ALCS average and two homers, he was named the ALCS MVP. Williams collected just four hits in the 1996 World Series but his 4 RBI led the Yankees and a clutch homer in the eighth inning of Game 3 helped capture the team’s first championship since 1978.

Following the 1997 season, Williams again was the subject of trade rumors, this time involving the Detroit Tigers. According to The New York Times sportswriter Murray Chass, Williams was nearly dealt to the Tigers for a package of young pitchers including Roberto Durán and first round draft pick Mike Drumright. Tigers general manager Randy Smith believed a deal had been reached and an official announcement was close, but Yankees general manager Bob Watson denied that was the case, and Williams remained a Yankee. Watson also discussed Williams with the Chicago Cubs in a potential trade involving Lance Johnson.

During the 1998 season, in which the Yankees went 114–48 to set a then American League regular season record, Williams finished with a .339 average, becoming the first player to win a batting title, Gold Glove award, and World Series ring in the same year.

After the 1998 season, Williams signed a seven-year, $87.5-million contract with the Yankees, one of the largest in baseball at the time. The Boston Red Sox and Arizona Diamondbacks also bid for Williams on the free agent market. For the length of the contract, the Yankees made the playoffs every single year, and as a result Williams continued to add to his postseason statistics, placing in the top 10 of various career postseason categories.

Williams signed with Paul McCartney’s publishing company, MPL Communications, and his major label debut, The Journey Within, was released on June 22, 2003. In addition to playing lead and rhythm guitar, Williams composed seven songs for the album. Tracks like “La Salsa En Mi” and “Desvelado” mix his love of jazz with Latin rhythms.

The last year covered by his contract, 2005, proved to be a difficult one. He started 99 games in center field and 22 games as designated hitter, but his already weak arm was highlighted as his fielding and batting abilities considerably weakened. He had a career-worst .321 OBP and batting average on balls in play (.274). As expected, the Yankees announced on August 2, 2005, that they would not pick up the $15 million option on Williams’ contract for the 2006 season, opting to pay a $3.5 million buyout instead. In December Williams was offered arbitration by team general manager Brian Cashman to allow an additional month for negotiation. On December 22, the Yankees re-signed Williams to a 1-year, $1.5 million contract.

In 2006, Williams saw a good amount of playing time in the corner outfield spots with both Hideki Matsui and Gary Sheffield out with wrist injuries, and did spot duty in center field on days when starting center fielder Johnny Damon was given time off to rest, playing more than was expected when he signed his one-year extension with the Yankees in 2006.

Williams played for Puerto Rico in the 2006 MLB World Baseball Classic, joining Carlos Delgado, Carlos Beltrán, Mike Lowell, Javier Vázquez, and José Vidro amongst others representing the island possession in a team managed by St. Louis Cardinals third base coach Jose Oquendo. Williams hit 2 homeruns in the 2006 WBC.

On July 26, 2006, Williams got his 2,300th career hit, becoming the 11th active player in the Majors with 2,300 or more career hits. Williams continued to climb the Yankees record books by hitting his 443rd career double on August 16, 2006, surpassing then-bench coach Don Mattingly for second-most as a Yankee. For the year, he walked only 7.3% of the time, a career-worst.

Williams’ contract expired at the end of the 2006 season. He had hoped to return to the Yankees in 2007 and was willing to accept a role as a back-up outfielder and pinch hitter. The Yankees offered Williams an invitation to spring training as a non-roster invitee, giving him a chance to compete for a job. Williams, however, wanted a guaranteed roster spot and declined the invitation.

On September 21, 2008, Williams made his first return to Yankee Stadium since 2006 for the ceremonies preceding the final game at the stadium. He was the last former player to be introduced and received a standing ovation that lasted a minute and 42 seconds.

After two years of inactivity, Williams returned to action playing for the Gigantes de Carolina in the Puerto Rico Baseball League (formerly LBPPR) interested in gauging his condition prior to a possible participation in the 2009 World Baseball Classic. MLB.com reported on December 30, 2008 that Williams had injured his quad while playing for Carolina and may not be able to play in the World Baseball Classic for Puerto Rico.

On February 19, 2009 Williams worked out with the Yankees at the team’s spring training complex. Williams hinted that if he performed well in the World Baseball Classic he might consider returning to the Yankees. Williams, a fan favorite with the Yankees during the Joe Torre era, still had several friends and former teammates in pinstripes.

In March 2009 he played for Puerto Rico in the World Baseball Classic, going 0-for-5 with two walks; after the series concluded, he expressed interest in playing in the Major Leagues again.

Williams’ second major album, Moving Forward, was released on April 14, 2009 under the Reform Records label. The album features fourteen tracks and includes some collaborative tracks with other artists such as Bruce Springsteen, Patti Scialfa, Jon Secada, and Dave Koz. Williams was nominated for a Latin Grammy Award for Moving Forward.

In 2010, Williams participated in the World Rhythms Tour with Basia. On July 18, 2010 he performed at the 2010 Central American and Caribbean Games opening ceremony.

In July 2011, Williams’ book, Rhythms of the Game, co-authored by Williams, Dave Gluck and Bob Thompson, with a foreword by Paul Simon, was to be published by Hal Leonard Publishing.

Williams was featured on the November/December 2011 cover of Making Music to discuss his life and career in music.

Williams appeared on the Hall of Fame ballot for the first time in 2012. He received 55 votes for 9.6%. The next year, Williams received 19 votes (3.3%). Since he received votes on fewer than 5% of ballots, Williams will not be eligible to appear on future ballots.

As of 2013, he holds the career postseason record for runs batted in (80). He is also second all-time for postseason home runs (22), doubles (29), total hits (128), total bases (223), and runs scored (83), and third in post-season games played (121). Standing on Yankee all-time lists as of the beginning of the 2008 season:

The Yankees announced in May 2014 that they would honor Williams with a plaque in Monument Park during the 2015 season. On February 16, 2015, the Yankees also announced that they would be retiring Williams’ number 51. On May 24, the Yankees unveiled Williams’s plaque and retired his number in a ceremony at Yankee Stadium.

Though he would not appear in a Major League Baseball game after 2006, Williams did not officially retire until 2015. At the February 2011 retirement press conference for Andy Pettitte, Williams acknowledged that his career was over and stated that he would officially announce his retirement soon thereafter. On April 22, 2015, it was announced that Williams would officially retire on April 24, 2015, with the Yankees.

In August 2015 Bernie Williams and Brandon Steiner made a surprise visit to Camp Adventure, and they helped revive the music program of KiDS NEED MORE, a charitable organization dedicated to creating camping experiences for children, families and young adults coping with cancer and life-threatening illnesses. The surprise visit aired September 15, 2015 on the YES Network on The Hook-Up: Camp Adventure.

Williams received his Bachelor of Music from the Manhattan School of Music on May 13, 2016.

In July 2018, Bernie Williams went out to Puerto Rico to take part in a special episode of Bar Rescue on the Paramount Network to help people affected by Hurricane Maria, rebuilding a bar and baseball field.