December 23, 1990: Montreal Expos trade Tim Raines to Chicago White Sox

December 23, 2025

By Kevin Glew

Cooperstowners in Canada

Thirty-five years ago today, the Montreal Expos traded Tim Raines to the Chicago White Sox for outfielder Ivan Calderon and reliever Barry Jones.

It was a deal that had been brewing for a couple of weeks.

Raines was a “10 and 5” player – meaning he had played 10 major league seasons and the last five with the same team – which gave him the right to veto a trade.

In a conversation with Expos GM Dave Dombrowski following the season, Raines did not request a trade, but he indicated he wouldn’t block one if he was dealt to one of the five National League teams – Atlanta Braves, Chicago Cubs, Los Angeles Dodgers, New York Mets or San Diego Padres – that played on natural grass.

Sold on White Sox

But when Raines saw the talented, young nucleus of the Chicago White Sox – Frank Thomas and Robin Ventura had just completed their rookie seasons – coupled with the natural grass at Comiskey Park, he warmed to the idea of going to the American League club.

“When the prospect opened that the White Sox were interested in me, I thought about it real hard, and I felt it wouldn’t be a bad idea after all,” Raines told the Chicago Tribune after the trade.

Of course, it didn’t hurt that the White Sox offered him a three-year deal worth more than $10 million and guaranteed him that he’d bat leadoff in 1991.

“They told me they want me to be their leadoff hitter,” Raines told the Montreal Gazette, “and that’s all I want. All through my career, that’s where I’ve been most productive and it’s good to be somewhere where they have confidence I can do the job.”

Though he had returned to the leadoff spot with the Expos toward the end of the 1990 season, he had hit second, third or cleanup at different times during the past three seasons.

“The last three years, I’ve been moved around in the batting order, and I wasn’t too fond of that,” Raines told the Chicago Tribune after the trade. “I always took pride in being a leadoff man. Now I get the opportunity to get back to my familiar role.”

Highest paid Expo

Raines, 31 at the time of the trade, had been the Expos’ highest paid player in 1990, making $2,178,888. And by his lofty standards, his numbers had declined. He batted .287 with a .379 on-base percentage with nine home runs and 49 stolen bases.

The trade ended Raines’ initial 12-season tenure with the Expos in which he developed into one of the best players in franchise history.

A fifth-round pick of the Expos in 1977, Raines was selected to seven consecutive All-Star games (1981 to 1987) and was named the MVP of the 1987 Midsummer Classic. During that same period, he also won a National League batting title in 1986 and topped the Senior Circuit in runs twice and in stolen bases four times.

In total in 1,452 games with the Expos (He returned for 47 games in 2001), Raines set franchise records in runs (947), stolen bases (635), triples (82), walks (793), and singles (1,163). He also ranks second in Expos history in batting average (.301) and hits (1,622).

In his first season with the Sox, Raines batted .268 and swiped 51 bases. In all, he suited up for five seasons on Chicago’s southside and batted .283 with a .375 on-base percentage and 143 stolen bases in 648 games.

Underwhelming return

Most Expos fans were underwhelmed at the return for Raines. They were hoping for a top-of-the-rotation starter, but the Expos settled for Calderon and Jones, a decent set-up man.

Calderon did put together a strong first season with the Expos, hitting .300 with 19 home runs and 32 stolen bases in 134 games. It was good enough to be selected to the All-Star Game. But Calderon would play just 48 games in an injury-riddled 1992 campaign before being dealt to the Red Sox.

Jones topped National League pitchers with 77 appearances for the Expos in 1991. He also had 13 saves and a 3.35 ERA. Following the season, he was traded to the Phillies for catcher Darrin Fletcher.

The Raines trade was another hard one to swallow for Expos fans who were growing weary of the club’s penny-pinching ways.

“I had incredibly mixed emotions about leaving Montreal,” Raines wrote in his 2017 autobiography, Rock Solid: My Life in Baseball’s Fast Lane. “On the one hand, I knew that it was time to tackle a new challenge in a new place for the second half of my career. My body started to feel the consequences of playing on the hard Olympic Stadium turf. The grass at the new Comiskey Park in Chicago, which opened during my first year with the White Sox, would give my legs a chance to stay fresh. I also saw that I no longer fit into the Expos’ long-term plans, if they had any at all.”

A few sentences later Raines added, “In my heart, I will always be an Expo. Every time I see that distinctive red-white-and-blue Expos logo, I feel stirrings from the past.”