Alex Bregman isn’t the first MLB All-Star whose free agency went to February

(Former?) Houston Astros star third baseman Alex Bregman remains a free agent and the best player available on the MLB open market. While Bregman, a Gold Glover and two-time All-Star, is definitely living the Will Smith Bel-Air meme all alone in the family room, he’s not the first high-level MLB player whose free agency went into February.

In chronological order, here are 10 All-Stars who didn’t sign a contract until February (contracts signed in the 2021-22 offseason aren’t included due to the lockout) — and in some cases beyond.

Ivan Rodriguez and the Detroit Tigers (2004)

Rodriguez signed a four-year, $40 million deal with the Tigers on Groundhog Day, giving them one of the best catchers in the game and a future Hall of Famer. The backstop continued to rake upon arrival, hitting .334 and driving in 86 runs in 2004. Rodriguez also led catchers in caught stealing percentage in both 2005 and 2006.

He went on to post a combined .298/.328/.449 slash line across his four-plus seasons in Detroit, which includes an appearance in the 2006 World Series.

Magglio Ordonez and the Tigers (2005)

Despite an injury-plagued 2004 season with the Chicago White Sox (52 games), the Tigers plucked Ordonez from their American League Central rivals on a five-year, $75 million deal. While his first season in Detroit was also limited by injury (82 games), Ordonez went on to hit at an MVP level from 2006-08. Registering 20-plus home runs and 100-plus RBIs in each of those three seasons and winning the 2007 batting title (.363) while also hitting a league-high 54 doubles, Ordonez justified Detroit’s financial conviction in him.

If it weren’t for Alex Rodriguez blasting 54 home runs and driving in 156 runs in 2007, Ordonez, a three-time Silver Slugger and six-time All-Star, would’ve also won an MVP.

James Shields and the San Diego Padres (2015)

Shields was part of a lively Padres offseason that also saw the franchise add All-Star outfielders Matt Kemp and Justin Upton and star closer Craig Kimbrel, among others. After Shields helped the Kansas City Royals get to the 2014 World Series and firmly established himself as one of the best right-handed pitchers in the sport, the Padres brought in the veteran on a five-year, $75 million deal to be their ace.

While Shields was respectable in his first season in San Diego (3.91 ERA and 216 strikeouts in 33 starts), his tenure didn’t go as planned, as his output declined and the Padres later traded him to the White Sox in 2016 — but received a future star by the name of Fernando Tatis in the deal.

Yu Darvish and the Chicago Cubs (2018)

Chicago chose to let a pitcher who was arguably its ace walk in free agency (we’ll revisit that) to bring in Darvish, an ace-caliber arm in his own right, on a six-year, $126 million deal. Darvish, a five-time All-Star, had a mixed bag of a career in Chicago. In year one, he pitched just eight games before suffering an eventual season-ending elbow injury, which he followed by posting a 3.98 ERA in 31 regular-season starts in 2019.

In the truncated 2020 season, Darvish was spectacular, posting a 2.01 ERA, 0.96 WHIP, 224 ERA+ and 93 strikeouts in 76.0 regular-season innings (12 starts). He was then traded to San Diego in an effort by the Cubs to shed payroll.

Eric Hosmer and the Padres (2018)

One of the last remaining core pieces of the 2015 World Series-champion Royals following the 2017 season, Hosmer signed an eight-year, $144 million deal with the Padres, which was the largest contract in franchise history at the time. Hosmer, a four-time Gold Glover, provided some credibility for the Padres, a building block and a proven left-handed bat.

However, his Padres’ career left some to be desired, as he posted an OPS north of .750 just once and was ultimately traded in the fifth year of his contract.

J.D. Martinez and the Boston Red Sox (2018)

It seemed inevitable that these two would find each other, and they did; it just happened post-Valentine’s Day on a five-year, $110 million deal. Coming off a career-high 45 home runs, Martinez came to Beantown and gave the Red Sox the extra oomph their lineup needed. In his first season with the Red Sox (2018), Martinez totaled 43 home runs and an MLB-high 130 RBIs en route to them winning the World Series.

Martinez finished his five-year stint in Boston with a combined .526 slugging percentage, three seasons with 25-plus home runs and three seasons with 95-plus RBIs. His well-rounded, impact bat from the right side was just what the doctor ordered for Boston.

Jake Arrieta and the Philadelphia Phillies (2018)

Yeah, the 2017-18 MLB offseason was extremely tedious. Putting a bow on it, Arrieta, one of the premier starting pitchers in the sport, didn’t sign until March, agreeing to a three-year, $75 million deal with the Phillies. For context, the right-hander established himself as a high-level starter in 2014, followed by winning the National League Cy Young with a remarkable 1.77 ERA and four complete games — three of them shutouts — in 2015. Part of the Cubs team that broke the Curse of the Billy Goat in 2016, Arrieta posted a combined 2.67 ERA, 1.03 WHIP and 151 ERA+ over his four complete seasons in Chicago (2014-17). Yet, the right-hander’s market didn’t develop the way he likely anticipated it would.

Unfortunately for Arrieta, while he had a respectable first season in Philadelphia (3.96 ERA over 31 starts), he suffered an elbow injury in 2019 and began to fizzle out; he last pitched in MLB in 2021.

Manny Machado and the Padres (2019)

The Padres wanted a franchise player and got just that — albeit late in the offseason — inking Machado to a 10-year, $300 million deal. Coming to San Diego in the prime of his career, Machado immediately became the face of the Padres and their veteran leader. He continued to wreak havoc in Southern California after six-plus seasons with the Baltimore Orioles and a half-season with the Los Angeles Dodgers. Across his six seasons with the Padres, Machado, a two-time Gold Glover and six-time All-Star, boasts a combined .275/.341/.490 slash line and has been electric at the hot corner.

Machado’s Padres’ tenure has been highlighted by helping them win their first playoff series in 14 years in just his second season (2020) and helping them reach the NL Championship Series in 2022.

Bryce Harper and the Phillies (2019)

After spending the first seven seasons of his career with the Washington Nationals, Harper signed with the NL East-rival Phillies for a then-stunning 13-year, $330 million deal. The deal included no opt-outs and a no-trade clause. Harper has lived up to every penny of that deal, as he won the NL MVP in 2021, the second such honor of his career, and helped the Phillies reach the World Series in 2022 and make the playoffs in each of the past three seasons. 

Across his six seasons in Philadelphia, Harper boasts a combined .285/.391/.533 slash line and has hit 30-plus home runs in three of his six seasons with the Phillies (2020 was a 60-game regular season, and Harper missed extensive time in 2022 and 2023). On top of it all, the formidable, left-handed hitter now plays first base. Harper was money well spent for the Phillies — and worth the wait.

Blake Snell and the San Francisco Giants (2024)

Snell has a case for the most distinct season and then free agency for any player in the history of American sports.

In 2023, Snell won the NL Cy Young, the second such honor of his career, with an MLB-best 2.25 ERA … and an MLB-high 99 walks with the Padres (they’re mentioned in this list a lot). Then, he didn’t ink a long-term deal all winter and settled for a two-year, $62 million deal with the Giants in March, which included an opt-out. After not making his first start until April 8, Snell struggled and was later placed on the injured list twice due to adductor and groin injuries, respectively. Then, he rebounded in emphatic fashion after returning to the mound in July, posting a 1.23 ERA across his final 14 starts, including throwing a no-hitter. Snell opted out after the season and proceeded to sign a five-year, $182 million deal with the Dodgers. In the end, it all worked out for the left-hander.

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