A top-flight reliever for much of the nineties, Montgomery owed much of his success to his boyhood hero Pete Rose. But not in the way he ever expected. Selected by the Cincinnati Reds in the 1983 draft, Montgomery had the opportunity to play for his idol when he was promoted to the bigs four years later. But after just 19 innings with the club in 1987, Rose told Reds GM Murray Cook the following February that Montgomery couldn’t play for him. A month later, the budding closer was traded to the Kansas City Royals for prospect Vin Snider.
As Snider floundered in the Reds’ farm system, Montgomery flourished in Kansas City. When Steve Farr got injured in August 1989, he stepped up as the main stopper for the last month and a half of the season. Although he saved 18 games with a 1.37 ERA and tallied 94 strikeouts in 92 innings, the Royals signed reliever Mark Davis, the NL Cy Young Award winner, in the offseason. But Davis started poorly in 1990, and Montgomery took advantage of the situation by recording 24 saves that year and 33 the next.
With Davis out of the picture, Montgomery was acknowledged as the club’s true closer in 1993. The new confidence that the title brought helped him to a career year, as he racked up 45 saves and a 2.27 ERA. But with the offensive explosion of the mid-’90s, Montgomery’s ERA would never be so low again. He did continue to notch the saves, averaging 24 a year for the rest of his career, but began to rely more on a change-up to baffle batters, as his overpowering fastball and slider lost a little of their velocity.
Despite a brief resurgence in 1998 that saw him total 36 saves, Montgomery’s high ERA (4.98) boded ill. Suffering from tendinitis in his right hip through the last couple of months of the following season, Montgomery ended up with a 6.84 ERA that year. However, he did enjoy a personal high when he notched his 300th save on July 25, 1999, becoming the tenth pitcher to reach the landmark, and the first to get them all with the same team. Montgomery retired at the end of the season ninth on the career saves list with 304, to be passed the following year by Rick Aguilera and John Wetteland.