Benjamin Hill travels the nation collecting stories about what makes Minor League Baseball unique. This excerpt from the Baseball Traveler newsletter, presented by Circle K, is a mere taste of the smorgasbord of delights he offers every week. Read the full newsletter here, and subscribe to his newsletter here.
Does the name Stan Wasiak ring a bell? If not, maybe it should.
Wasiak, "The King of the Minors," is Minor League Baseball's all-time winningest manager. He piloted 18 teams over 37 consecutive seasons, wrapping up his career in 1986 with a record of 2,530-2,314.
While no one has been able to match Stan the Man-ager in the wins column, one current skipper is getting very close and others are not far behind. As we enter the 2026 season, these are Minor League Baseball's winningest active managers.
Note: Win totals only reflect the manager's Minor League Baseball experience, not necessarily the entirety of his career.
Rick Sweet, Nashville Sounds (Triple-A MIL)
MiLB managerial debut: 1987
Organizations: Seattle, Houston, New York Mets, Montreal, San Diego, Detroit, Cincinnati, Milwaukee
Record: 2,438-2,234
Sweet enters the season just 92 wins shy of Wasiak on the all-time list and third overall (behind Bob Coleman’s 2,496), making him a virtual lock to claim the top spot in 2027 should he decide to keep managing. That would be 40 years after his managerial debut, when he led a Bellingham Mariners team that featured 17-year-old Ken Griffey Jr. on its roster. This year marks Sweet's sixth consecutive season with the Sounds and seventh overall. He is already that franchise’s all-time managerial wins leader; last season the team gave away a Rick Sweet bobble-stache.
Pat Kelly, Louisville Bats (Triple-A CIN)
MiLB managerial debut: 1986
Organizations: San Diego, Montreal, Cincinnati, Toronto, Atlanta
Record: 2,092-2,251
This article is about wins, yes, but Kelly tops Sweet in the losses column and is just 63 behind Wasiak's all-time mark of 2,314. He’s a Reds farm system stalwart, having managed eight teams in the organization since 2007. This season marks his sixth with the Bats; in 2024 he had the rare distinction of managing a squad that included his son, Casey, on the roster. That season he also notched his 2,000th career victory, making him one of just seven Minor League managers to achieve the feat.
John Shoemaker, Ontario Tower Buzzers (Single-A LAD)
MiLB managerial debut: 1987
Organization: Los Angeles Dodgers
Record: 1,915-1,806
This will be Shoemaker's 50th season (!) with the Dodgers, going back to when he was drafted by the organization as an infielder in 1977. The Ontario Tower Buzzers, entering their inaugural season in the California League, will be the 13th L.A. farm club that he's managed. Shoemaker is now just 85 victories away from joining Sweet and Kelly in the 2,000 wins club. All these decades later, it's strange to think about how his career could have gone in a different direction: Shoemaker was the Chicago Bulls' sixth-round draft pick in 1978.
Dave Brundage, Sacramento River Cats (Triple-A SF)
MiLB managerial debut: 1995
Organizations: Seattle, Atlanta, Philadelphia, San Francisco
Record: 1,908-1,923
Brundage's eight-year playing career, from 1986-94, was mostly at the Triple-A level. He's primarily managed at the Triple-A level as well, dating to his 2006 season at the helm of the Tacoma Rainiers. Brundage has been with Sacramento since 2017, and in 2026 should surpass Tony DeFrancesco as the River Cats' all-time wins leader (Brundage has 537 wins in Sacramento; DeFrancesco had 578). Like Shoemaker, Brundage is on pace to notch his 2,000th win in 2027.
Marty Pevey, Iowa Cubs (Triple-A CHC)
MiLB managerial debut: 1996
Organizations: Toronto, Chicago Cubs
Record: 1,466-1,511
Pevey, a catcher by trade, played 13 seasons professionally (including a 13-game stint with the Montreal Expos in 1989). He then immediately transitioned to a managerial role, leading teams throughout the Blue Jays organization from 1996-2005. He joined the Cubs organization in 2009 following a stint as Toronto’s first base coach, and since 2013 has served as the manager of the Iowa Cubs. He now has 822 wins at the helm of this Des Moines-based franchise, a formidable total in and of itself.
Who's next on the list?
6. Mike Guerrero (Biloxi Shuckers, Double-A MIL) – 1,445-1,275
7. Kevin Boles (Montgomery Biscuits, Double-A TB) – 1,431-1,427
8. Pedro Lopez (Albuquerque Isotopes, Triple-A COL) – 1,167-1,238
9. Al Pedrique (Reading Fightin Phils, Double-A PHI) – 1,127-1,094
In memoriam
Minor League Baseball lost a managerial titan in 2025, as Buddy Bailey passed away on Sept. 22 at the age of 68. Between 1983 and 2024 Bailey spent 35 seasons as a manager, notching 2,417 wins (fourth all-time behind Wasiak, Coleman and Sweet). He was also a Venezuelan Professional Baseball League legend, having led the Tigres de Aragua to six winter ball titles.