During the 1997 season, Howry was one of six prospects (along with Keith Foulke, Lorenzo Barceló, Mike Caruso, Ken Vining, and Brian Manning) traded to the White Sox in exchange for Wilson Álvarez, Danny Darwin, and Roberto Hernández in what became known as the White Flag Trade.

[1] He made his major league debut with the Chicago White Sox in 1998 and served as the team's closer, saving 28 games in 1999 until being replaced by Keith Foulke in early May 2000.

He was dealt to the Boston Red Sox in 2002, but suffered right elbow problems that forced him to be put on the 60-day disabled list in late 2003.

[2] Howry filled in for an injured Ryan Dempster during the 2007 playoff run, earning eight saves with a 3.32 ERA, and was one of the Cubs' primary relievers in 2008, sometimes serving as setup man to All-Star closer Kerry Wood.

[3] After the Cubs declined arbitration, Howry signed a $2.75 million, one-year contract with the San Francisco Giants on December 3, 2008.