Editing Jose Canseco (section)

====Final seasons (1999–2001)====
Despite hitting a career-high 46 home runs in 1998, the 33-year-old Canseco drew minimal attention in the free agent market. In 1999, he signed a one-year contract with the [[Tampa Bay Rays|Tampa Bay Devil Rays]] worth $3.3 million with incentives to be their Designated Hitter. According to Canseco, the contract included a clause stating that if he was elected to the Hall of Fame, he would be depicted as a member of the Devil Rays. That year, he came out of the gate swinging, hitting a home run on Opening Day and reaching a total of 10 home runs by the end of April. On April 14 he hit home run number 400 of his career against Toronto's [[Kelvim Escobar]]. From May 16 to 21, he hit a home run in five consecutive games, the second-longest streak in Tampa Bay history. In his first 60 games played, he hit 25 home runs, batting .306 with a .690 slugging percentage. On pace for a 60+ home run season, he was voted to the All-Star team as the starting DH for the American League (Tampa Bay's first position player ever to be selected to the All-Star Game), making it his first selection in seven years. By the All-Star break, Canseco was leading the American League with 31 home runs, while playing in 82 games during the first half of the season, and became the 14th player in MLB history to hit 30+ home runs before the All-Star break. However, he injured his back days before the mid-summer classic and missed the game, and was replaced by [[Rafael Palmeiro]]. He also missed the Home Run Derby at Boston's [[Fenway Park]] and the chance to compete against Bash Brother Mark McGwire. He had back surgery and was expected to miss the rest of the season. With a remarkable recovery, he came back into action on August 20, less than a month and a half after his back operation. After his return, Canseco was hitting .315 with only 2 home runs but had 18 RBIs and 23 hits in his first 20 games back. Although he only hit 3 more home runs in 115 at-bats after his injury, he had a .287 batting average with 26 RBIs and 33 hits in his last 31 games of the year. He finished the season with 34 home runs and 95 RBIs with a .276 batting average and was ninth in the league with a .563 slugging percentage.<ref name="BR4" />

Despite missing around 350 games since 1990, mostly due to injuries, by the end of 1999, Canseco had a total of 303 home runs in 1,145 games, which placed him eighth in the majors during the 1990s. In 5 seasons during the 90's, he was in the Top-10 list for home run hitters in the American League.

In February 2000, before the start of spring training for the following MLB season, Canseco played in the [[MLBPA]]-organized ''Big League Challenge'' home run derby in [[Las Vegas]] at [[Cashman Field]]. He competed against a field of 12 that included notable sluggers such as [[Mark McGwire]], [[Barry Bonds]], [[Sammy Sosa]], and [[Mike Piazza]].<ref>{{cite news|url=https://lasvegassun.com/news/2000/feb/11/sluggers-eager-to-show-off-long-ball-prowess/|title=Sluggers eager to show off long-ball prowess |first=Steve|last=Guiremand|date=February 11, 2000|work=[[Las Vegas Sun]] |access-date=September 13, 2024 }}</ref> Canseco won the tournament, defeating [[Rafael Palmeiro]] in the final.<ref>{{cite web|url=https://www.psacard.com/articles/articleview/2174/heavy-hitters-going-deep-charity|title=Heavy Hitters Going Deep for Charity|first1=Joe|last1=Orlando|date=March 17, 2000|website=[[Professional Sports Authenticator]]|access-date=September 13, 2024|archive-url=https://web.archive.org/web/20170731064620/https://www.psacard.com/articles/articleview/2174/heavy-hitters-going-deep-charity |archive-date=July 31, 2017 |url-status=dead }}</ref>

The Devil Rays re-signed Canseco for the 2000 season on a $3-million contract. The Devil Rays traded for third baseman [[Vinny Castilla]] and signed [[Greg Vaughn]] as a free agent to complement [[Fred McGriff]] and Canseco in the lineup. However, injuries caused the Tampa Bay front office to disband the quartet after the trade deadline. The first half of the season was one of the most difficult in Canseco's career. Bothered by a foot injury, he missed 41 of the team's 85 games up to the All-Star break. Canseco ended his Tampa Bay tenure on August 7 when he was claimed off waivers by the [[New York Yankees]]. In one and a half seasons with the Devil Rays, Canseco had a slash line of .272/.373/.525 with 43 home runs, 33 doubles, 125 runs batted in, and 176 hits on 174 games. At the time of the waivers' claim, Canseco's 440 career home runs were the most ever for any player acquired by the Yankees. The move to the Yankees caught many, including [[List of New York Yankees managers|Yankees manager]] [[Joe Torre]], off guard, as the Yankees had other players at the time who fulfilled similar roles, such as [[Dave Justice]] and [[Glenallen Hill]].<ref>{{cite news|url=https://www.nytimes.com/2000/08/08/sports/baseball-yanks-get-canseco-but-the-question-is-why.html?scp=2&sq=Jose+Canseco&st=nyt|work=The New York Times|first=Buster|last=Olney|title=Baseball; Yanks Get Canseco, but the Question Is Why?|date=August 8, 2000|page=D1|access-date=September 13, 2024}}</ref> [[List of New York Yankees owners and executives|Yankees General Manager]] [[Brian Cashman]] made the claim to prevent the Athletics, Red Sox, and Blue Jays, who were in a close race with the Yankees, from acquiring Canseco.<ref name=worsttime/>

On August 10, during his first game in the starting lineup with the Yankees, batting fourth as the DH, Canseco went 2-for-2 with a walk, a home run, 2 sacrifice flies, and 3 RBIs. He hit .243 with 6 home runs and 19 RBIs in 37 games for the Yankees, splitting duties as a DH, outfielder, and pinch hitter.<ref name="BR4" /> For the entire season, he had 15 home runs and 49 RBIs in 329 at-bats.<ref name="BR4" /> The Yankees won the AL East, but Canseco was not on the team's roster for the Division Series or the ALCS. He was, however, included in the final roster for the World Series against the [[New York Mets]]. During the sixth inning of Game 4 of the World Series, manager Joe Torre noticed that no right-handed pitcher was warming up in the Mets bullpen, and with pitcher [[David Cone]] next to bat, Torre sent Canseco to the plate to face left-handed [[Glendon Rusch]] as a pinch hitter (his most recent World Series at-bat was also as a pinch hitter in Game 4 of the 1990 World Series, 10 years prior). The game was the first in which Canseco had played in 24 days, and he struck out. The Yankees won the series 4 games to 1 and Canseco earned his second [[World Series ring]]. Canseco later called his Yankees tenure "the worst time of [his] life" due to receiving limited playing time.<ref name=worsttime>{{cite news|url=https://www.nytimes.com/2001/03/26/sports/baseball-notebook-canseco-calls-yankee-tenure-the-worst-time-of-my-life.html|work=The New York Times|first=Buster|last=Olney|title=Baseball: Notebook; Canseco Calls Yankee Tenure 'The Worst Time of My Life'|date=March 26, 2001|page=D10|access-date=September 13, 2024 }}</ref> His short stint with the Yankees marked the third time he was [[Roger Clemens]]' teammate, a fact later magnified by the media due to the steroid controversy, the [[Mitchell Report]], and the infamous pool party at Canseco's house two years prior while both played with the Blue Jays. In November, the Yankees declined Canseco's $5-million option and paid the $500,000 buyout, with Canseco becoming a free agent.

On January 16, 2001, the [[Los Angeles Angels|Anaheim Angels]] signed Canseco to an incentive-laden deal heavily based on plate appearances. After only 39 spring training at-bats, in which he hit .231 and no home runs, the Angels cut Canseco. He lost the Anaheim DH spot to Glenallen Hill, with whom he shared at-bats for the Yankees the year prior. (Hill was released by the Angels in June, after hitting .136 with 1 home run in 16 games for the 2001 season, his last in the majors). Canseco spent half of the season with the [[Newark Bears]] of the independent [[Atlantic League of Professional Baseball|Atlantic League]], alongside his twin brother [[Ozzie Canseco]], before joining the [[Chicago White Sox]] on June 21 to replace [[Frank Thomas]] as the every day designated hitter. Wearing jersey number 31 during his first game back in the majors since the 2000 World Series, he went 1-for-5 with a double as the DH, hitting fifth in the lineup. He had 3 RBIs in his second game of the season. His first home run came on June 26 against the [[Minnesota Twins]]. During the season he had two 2-homer games, one on July 8 and another on August 1. He finished the season playing in 76 games, hitting 16 home runs and 49 RBIs in only 256 at-bats, a pace of 30+ home runs and 100+ RBIs had he played the entire season.<ref name="BR4" /> His last home run of the season was the 462nd for his career, and came against [[Mike Mussina]] of the New York Yankees, putting Canseco just 38 home runs away from reaching the 500-home run milestone, at age 37.

In the spring of 2002, Canseco was signed to a minor league contract by the [[Montreal Expos]], who were at the time owned by Major League Baseball, had [[Omar Minaya]] as general manager and [[Frank Robinson]] as manager. Despite making only 13 appearances in the outfield in the previous three years, he was expected to be the Expos' left fielder, and the designated hitter during inter-league play, in what would have been Canseco's first time playing for a National League club. He played 14 preseason games, batting .200 with 3 home runs (tied for the team lead) and 5 RBIs. However, he was again released prior to the regular season start, this time four days before Opening Day. The Expos invited Canseco to be part of their Triple-A team, but he declined the offer. With Opening Day scheduled for March 31, Canseco did not find a team looking for a DH and signed a minor league contract with a White Sox affiliate, the [[Charlotte Knights]], for whom he hit .172 with 5 home runs in 18 minor league games. 
Only 38 home runs shy of 500 for his career, Canseco officially announced his retirement from Major League Baseball on May 13, 2002. At the time of his retirement, Canseco had 1,942 career strikeouts, second all time only to Reggie Jackson. By the end of the 2024 season, he is 10th on the all-time list for hitters with the most strikeouts.

At 39 years old he made a brief comeback attempt in 2004, attending an open tryout with the Los Angeles Dodgers, but was not offered a spot with the team nor with any of their minor league affiliates.