Following last week’s trade deadline deals, Ryan Tepera and Craig Kimbrel became the 36th and 37th people I’ve seen play in person for both the Cubs and the White Sox. With the first round of crosstown kicking off this afternoon at Wrigley, here’s a look at those players, in alphabetical order.
David Aardsma
After posting a decent season with the Cubs in 2006, Aardsma was traded to the White Sox for Neal Cotts. Aardsma lasted one season with the Sox, where he was unable to duplicate his success from the year before.
Jason Bere
Drafted by the White Sox in the 36th round in 1990, Bere debuted with the big league club in 1993, finishing 2nd in Rookie of the Year voting. After an All Star selection in 1994, injuries marred the remainder of his tenure on the South Side, which ended in 1998. He resurfaced with the Cubs in 2001 and had a decent season, but he went 1-10 in 2002 before being let go.
Emilio Bonifacio
Bonifacio spent back-to-back partial seasons in Chicago, first for the Cubs in 2014 after signing as a free agent, where he played decently enough to be flipped at the trade deadline, along with James Russell, to the Braves for a young catching prospect by the name of Victor Caratini. He returned to Chicago in 2015, signing with the White Sox, where he he did not do well at all, hitting .167 in 47 games before being released in August.
Welington Castillo
Debuting with the Cubs in 2010, Castillo spent time behind the plate for the Cubs until May of 2015, when, having been replaced in the starting lineup by Miguel Montero, he was flipped to the Mariners. He returned to Chicago in 2018 after signing with the White Sox as a free agent. On May 24th of that season, he was suspended 80 games for a violation of the PED policy. The White Sox then cut bait following the 2019 season, shipping him off to the Rangers.
Neal Cotts
Acquired by the White Sox in the Billy Koch trade, he debuted with the team in 2003. He was a key contributor in the bullpen during the 2005 championship season, and was the only relief pitcher to appear in all 3 rounds of the playoffs that season. Following the 2006 season, he was traded to the Cubs for David Aardsma, and he spent the next 3 injury filled seasons on the North Side.
Scott Eyre
Joining the White Sox organization in a 1994 trade with the Rangers, he debuted with the big league team in 1997. He split the next 4 seasons between the rotation and the bullpen, not to mention between Chicago and Charlotte, before being moved to the Blue Jays following the 2000 ALDS loss to the Mariners. He joined the Cubs as a free agent for the 2006 season and enjoyed 2 seasons of relative success, before falling apart in 2008, when he was traded to the Phillies.
Kosuke Fukudome
He became the first Japanese player in Cub history when he made his debut in 2008. After an initial All Star berth that year, he faded over the next 4 seasons until he was traded to the Indians at the deadline in 2011. He signed with the White Sox for 2012, but was not particularly effective and was released in June.
Tom Gordon
After missing the 2000 season due to injury, he signed with the Cubs as a free agent. He saved 27 games in 2001 and then was hurt in 2002, appearing in only 19 games prior to his August trade to the Astros. He signed with the White Sox that offseason and had a good 2003 season on the South Side.
Jeff Gray
Acquired by the Cubs from the A’s in the Jake Fox deal, he appeared in 7 games for the team in 2010. He signed with the White Sox as a free agent and appeared in 6 games for them in April 2011, before being claimed on waivers by the Mariners.
Derek Holland
Signed as a free agent prior to the 2017, Holland initially looked like just what the White Sox were looking for, posting a 2.37 ERA in his first 10 starts, but then regressed to the point that he was released in September, despite the expanded rosters. He came to the Cubs from the Giants at the trade deadline in 2019, appearing in 20 games with an ERA hovering around 7.00.
Bob Howry
Acquired in the infamous White Flag trade of 1997, Bob Howry debuted with the White Sox the following year, becoming a mainstay of the bullpen until his 2002 trade to the Red Sox. He signed as a free agent with the Cubs prior to the 2006 season, where he would spend the next 3 years. He rejoined the Cubs in 2010 for a little over 2 months to finish out his career.
Austin Jackson
Acquired by the Cubs in a waiver trade on August 31, 2015, Jackson appeared in 29 games down the stretch as the Cubs snared the second Wild Card spot and propelled themselves to a NLCS appearance. Jackson went 0 for the post-season, making it into 6 games as a defensive replacement. He signed with the White Sox as a free agent the following March, but a knee injury cut his season short in June.
Edwin Jackson
Acquired by the White Sox in an aborted 2010 attempt to get Adam Dunn from the Nationals, Jackson spent just under 1 calendar year with the team, being traded to the Blue Jays the following July. He signed a 4 year deal with the Cubs prior to the 2013 season, and he was been a tremendous bust, eventually being released in 2015.
Craig Kimbrel
After draft pick compensation left him unsigned into June of 2019, the Cubs gave him a 3 year deal, with an option for 2022. With no spring training and a balky knee, Kimbrel struggled for the remainder of the year and into 2020, before rediscovering the form that made him one of the best closers in baseball history. That improvement led to him being traded to the White Sox as part of the Cubs’ fire sale at the deadline in 2021.
Jon Jay
Jay joined the Cubs following their 2016 World Series title, hitting .296 in 379 at bats and pitching an inning of scoreless relief during a blowout loss to the Brewers. He joined the White Sox two years later, spending nearly the first three months of the season on the DL and appearing in only 47 games before undergoing season ending hip surgery on August 30.
Lance Johnson
Acquired by the White Sox in 1988, Lance Johnson became the teams leadoff hitter and center fielder for most of the next 8 seasons. In 1997, he was traded to the Cubs in the Brian McRae trade, and he would remain on the North Side until being released following the 1999 season.
Matt Karchner
Matt Karchner was acquired by the White Sox from the Royals via the minor league draft in 1993, making his major league debut on July 18, 1995. He would remain in the White Sox bullpen until 1998 when the Cubs, in the midst of a battle for the NL Wild Card, sent a young pitcher named Jon Garland to the White Sox for Karchner. He disappointed the Cubs until he was released in September of 2000.
Vance Law
Vance Law was acquired by the White Sox in a 1982 trade with the Pirates. He would become their primary third baseman until his trade to the Expos following the 1984 season. He signed as a free agent with the Cubs prior to the 1988 season, where he would remain for 2 seasons, becoming one of the few modern players to appear in the post-season for both organizations.
Darren Lewis
Darren Lewis signed with the White Sox as a free agent prior to the 1996 season, and he spent the next year and a half with the team until his August 1997 trade to the Dodgers. He joined the Cubs as a free agent in 2002, before being traded to the Pirates at the deadline.
Brent Lillibridge
Brent Lillibridge joined the White Sox in the deal that sent Javier Vazquez to the Braves following the 2008 season. He spent the next 3 1/2 years with the Sox, hitting the 10,000th home run in franchise history in 2011, until being traded to the Red Sox in 2012. He signed as a free agent with the Cubs for 2013, but appeared in only 9 games with them.
Kenny Lofton
Kenny Lofton spent half a season on each side of town, spending the first half of 2002 on the South Side until being traded to the Giants, and then the second half of 2003 on the North Side after being acquired from the Pirates.
Dave Martinez
Drafted by the Cubs in the 3rd round of the 1983 draft, he made his debut with the big league club in June of 1985. He was traded to the Expos in July of 1988, after allegedly having his way with Ryne Sandberg’s wife. He joined the White Sox as a free agent in 1995 and spent the next 3 seasons on the South Side. He returned to the Cubs in 2000 for 18 games between stints with the Rays and the Rangers.
Chuck McElroy
Acquired by the Cubs in April of 1991 in the deal that sent Mitch Williams to the Phillies, McElroy became a mainstay of the Cub bullpen for the next 3 seasons until being traded to the Reds in December of 1993. In May of 1997, he was traded by the Angels to the White Sox, and he finished out the year on the South Side before being lost in the expansion draft.
Dioner Navarro
Navarro signed a free agent deal with the Cubs for the 2013 season, notching his first multi-HR game in May against the cross-town White Sox. 3 years later, he signed on with the White Sox, where he hit a disappointing .210 with 6 home runs in 85 games.
Jaime Navarro
Jaime Navarro signed a free agent deal with the Cubs in 1995 and spent the next 2 years toiling on the North Side. In December of 1996, he became one of, if not the worst free agent signing in White Sox history, putting up an ERA over 6 until he was mercifully traded to the Brewers in 2000.
Will Ohman
Drafted by the Cubs in the 1998 draft, he debuted with the team in 2000 and spent 5 of the next 7 seasons with the big league club. He signed with the White Sox as a free agent in 2011 and spent the next year and a half in their bullpen, until being released.
Mike Olt
Olt, among others, was acquired by the Cubs near the trade deadline in 2013 from the Rangers for Matt Garza. Olt made the opening day roster in 2014 and split time with Luis Valbuena, before being sent back down to Iowa. He started the 2015 season as the primary third baseman, until a broken wrist in April led to the promotion of Kris Bryant. He was DFA’d at the end of August and claimed off of waivers by the White Sox. He hit .203 in 24 games and became the only player in MLB history to hit a home run for both Chicago teams in the same season. He was then waived by the White Sox the following spring.
Josh Paul
The Chicago area native was drafted by the White Sox in the 2nd round of the 1996 draft and made his major league debut with the team in 1999. He stayed with the team until being let go in 2003. He signed with the Cubs a week later and appeared in 3 games for the North Siders.
Juan Pierre
Juan Pierre was traded by the Marlins to the Cubs prior to the 2006 season. He spent one year on the North Side before leaving as a free agent. He returned to Chicago after the 2009 season, when he was traded by the Dodgers to the White Sox. He spent the next 2 seasons leading off and playing left field for the South Siders.
Jose Quintana
Originally signed by the White Sox as a minor league free agent after the 2011 season, Quintana and made his major league debut on May 7, 2012. He became a steady, if unlucky, member of the starting rotation, putting together a a career mark of 50-54 with an unbelievable 65 no decisions. In July of 2017, with the Cubs looking to defend their World Series title and the White Sox looking to rebuild, the two teams pulled off a trade, sending Quintana to the Cubs and Eloy Jimenez and Dylan Cease amongst the haul for the White Sox. In 3+ seasons with the Cubs, he improved his career winning percentage, but wasn’t the difference maker the team thought they were getting. He became a free agent following the 2020 season.
Clayton Richard
Drafted by the White Sox in 2005, he debuted in 2008, splitting time between the rotation and the bullpen. At the trade deadline in 2009, he was part of the package that brought Jake Peavy to the south side from San Diego. In 2015, Richard was traded to the Cubs, where he started, relieved, and was DFA’d twice, the first time accepting an outright assignment to Iowa and the second, electing to become a free agent. He resigned with the Cubs two days later and finished the season with the team. He returned to the Cubs in 2016, though was released when they acquired Aroldis Chapman.
Jeff Samardzija
Drafted by the Cubs in 2006, he debuted in 2008 and remained with them until his in July 2014 to the A’s. The following offseason, the A’s flipped him to the White Sox, where he spent one disappointing season.
Sammy Sosa
Acquired by the White Sox in the 1989 trade that sent Harold Baines to the Rangers, Sosa roamed the outfield for the Sox until the end of spring training in 1992, when he was traded to the Cubs for George Bell. He became a superstar with the Cubs, surpassing 60 home runs 3 times, until becoming a pariah in 2004.
Geovany Soto
Drafted by the Cubs in the 2001 draft, he made his major league debut with the team in 2005 and became the NL Rookie of the Year in 2008. He remained with the Cubs until the trade deadline in 2012, when he was sent to the Rangers. He joined the White Sox in 2015 on a minor league deal and earned the backup catcher spot in spring training. He had a second stint with the White Sox in 2017.
Ryan Sweeney
The 2nd round pick of the White Sox in the 2003 draft, Ryan Sweeney debuted with the White Sox in 2006. He had cups of coffee in 2 straight Septembers before being sent to the A’s in the horrible Nick Swisher deal. Sweeney signed with the Cubs as a free agent prior to the 2013 season and spent 2 years with the North Siders before being released.
Ryan Tepera
Acquired by the Cubs as a free agent prior to the 2020 season, Tepera spent the pandemic-shortened season on the North Side, picking up an inadvertent MVP vote thanks to a point and click error. He was non-tendered in the offseason, but eventually resigned with the Cubs. Following a successful start to the 2021 season, he was dealt to the White Sox at the deadline, where, to date, he has had an inauspicious start.
Luis Vizcaino
Acquired by the White Sox from the Brewers in the Carlos Lee deal, he spent the 2005 season with the team, earning a World Series ring in the process. Following the season, he was traded to the Diamondbacks. In January of 2009, he was traded by the Rockies to the Cubs for Jason Marquis. He appeared in 4 games before being released in early May.