When compiling this list, it would’ve been easy (and boring) to list the managers with the worst win-loss records in the history of baseball. But we seek to entertain you and some of these guys on our list are true characters.

We tried to stick with recent managers that failed during a 162-game schedule. So although all 25 might not be the worst managers in the history of the game, they are all really bad for one reason or another. 

25. Don Wakamatsu

After a respectable 85-77 season in 2009 and offseason signings of Cliff Lee and Chone Figgins, many experts picked the Mariners to win their division in 2010. Instead, Wakamatsu was in charge of a 42-70 (.375) nightmare of a season that ended when he was canned in August.

The fearless Don, the first Japanese-American manager in major league history, had countless spats with star players Ken Griffey Jr., Figgins and Milton Bradley, but his most memorable fit was a shouting and shoving match with Jose Lopez during a home game. 

24. Mike Hargrove

The “Human Rain Delay” won five straight division titles with Cleveland from 1995 to 1999, but he makes this list for what he did afterwards. In four seasons with Baltimore from 2000 to 2003, he averaged less than 69 wins per season, going 275-372 (.425).

He also batted the great Cal Ripken Jr. seventh in the lineup in his final game as an Oriole on Oct. 6, 2001, leaving Ripken on deck to watch his Hall of Fame career end when Brady Anderson struck out. The other Oriole greats that batted before Ripken in the lineup that day were Tim Raines Sr., Luis Matos, Jeff Conine, Chris Richard and Tony Batista.

Was it any wonder why this team lost 98 games in 2001? “Grover” also had a lackluster two-and-a-half seasons with Seattle from 2005-07, going 192-210 (.478) and two last-place finishes in the AL West. 

23. Tony Pena

He seems like a pretty classy guy, and was a quality major leaguer, but his managerial record deserves some serious heckling.

When he took over the Royals in 2002, he didn’t have a whole lot of talent to work with, and it showed as he guided K.C. to a 49-77 record (.389). However, Pena worked wonders with the Royals, leading them to a 83-79 mark and a third-place finish in the division. Everything really went south in the next two seasons, as Pena’s club went 58-104 in 2004 and then he was shown the door after an 8-25 start (.242) to the 2005 season.

22. Willie Randolph

Randolph took over the reins in New York in 2005, and led the Mets to the NL East Division crown in 2006 with 97 wins, losing in Game 7 of the NLCS to St. Louis. The next season, most pundits expected New York to take that next step and reach the World Series. And after a 4-3 win over Atlanta on September 12 put them seven games up on the Phillies for the division lead with just 17 games remaining, Mets fans were making postseason plans.

But the bottom quickly fell out of New York’s season as five straight losses (three to Philadelphia, two to lowly Washington) reduced the NL East lead to just 1.5 games. And the always-confident Randolph watched in horror as his team closed the season with six losses in the final seven games (all at home), capped off by an 8-1 drubbing to Florida.

Randolph will ultimately be the scapegoat for this epic choke, and he was unable to regain the trust of the Mets brass, which fired him after a 34-35 start in 2008—despite the fact that he won three of his final four games managed.

21. Ted Williams

“There goes the greatest hitter who ever lived.”

Maybe so, but managing was never Teddy Ballgame’s bag. The Splendid Splinter led the Washington Senators to a solid 86-76 record in his managerial debut in 1969, but won less than 40 percent of his games in his final three seasons.

Thumper got progressively thumped more and more each year, going 70-92 with Washington in 1970, 63-96 in 1971 and then 54-100 with the Texas Rangers in 1972. 

20. Ned Yost

He was so bad that the Brewers canned him on September 15, 2008 when they were 16 games above .500 and tied for the NL Wild Card lead. Yost’s Milwaukee club started that September 3-11 in its first 14 games of the month.

GM Doug Melvin summed up the firing by saying in a news conference that “When we talked to (Ned), he didn’t have all the answers as to what’s gone on the last two weeks.”

Yost hasn’t seemed to find any answers in his stint with Kansas City. After taking over in 2010 and going 55-72 to cement the Royals in last place for the season, Yost has guided K.C. to a 37-54 mark in the first half of the 2011 season, which is the worst record in the American League.

19. Dave Trembley

This entire list could be comprised of Orioles, Royals and Pirates managers, but Trembley truly earned his place with a sub-.400 winning percentage in nearly 500 games as the Orioles skipper. His high-water mark was 40-53 to finish off the 2007 season and keep Baltimore out of last place.

But his final three years all ended up in the AL East basement: 68-93 in 2008, 64-98 in 2009 and an embarrassing 15-39 mark (.278) last year before finally getting the axe.

18. John Russell

It’s tough to dump on a Pirates manager in recent years, but Mr. Russell is well deserving of this list after racking up 299 defeats in three seasons. After a high-water mark of 69-85 in his first season in Pittsburgh in 2008, Russell lost 99 games in 2009 and ended his Bucs tenure with a 57-105 record in 2010. In his final year, Pittsburgh won a mere 21 percent of its road games, going 17-64.

All totaled, Russell’s .384 winning percentage is the worst among National League managers since 1970 (minimum 320 games).

17. Hal McRae

The You Tube sensation might have been temporarily insane during his media-induced tirade in 1993, but it never stops being must-see TV.

In terms of his managerial record, that is also rather amusing, especially his final stint with Tampa Bay in 2001-2002 when he went 113-196 (.366). But to be fair, McRae did a great job with Kansas City, posting a winning record from 1991-94 (286-277) with a couple of third-place division finishes. 

16. Butch Hobson

The Butcher was famous for many things during a brilliant athletic career. He was a star football player at Alabama under Bear Bryant, before hitting 30 HR and 112 RBI for Boston in 1977 and committing 43 errors with a sub-.900 fielding percentage for the Sox in 1978.

His MLB managerial career also had its moments, but none were very good. He took over his beloved Red Sox in 1992 and went 73-89, which landed Boston in last place in the seven-team AL East. He nearly reached .500 in 1993, going 80-82, but he was finished after the strike-shortened ’94 campaign after a subpar 54-61 record. 

Two years later, as the skipper for Triple-A Scranton/Wilkes-Barre (Phillies), he was fired after being arrested for possession of cocaine. His story has a somewhat happy ending though. He has since managed a couple of minor league championships and is currently the skipper of the Lancaster Barnstormers of the Atlantic League.

15. Marcel Lachemann

In one of the forgotten pennant-race chokes in baseball history, Marcel Lachemann was at the helm of the Angels in 1995, and on August 24, his team had an 8.5-game division lead. Even after nine straight defeats, the Halos righted the ship for the next week, and held a six-game lead in the AL West on Sept. 12.

But nine consecutive losses later, the division lead was permanently squandered and the Halos missed the postseason.

Lachemann was brought back in 1996, but was shown the door after a 52-59 start to a season in which California eventually finished in the AL West cellar.

14. Don Mattingly

Is it really a surprise that a guy who has never won anything at a major league level has led Los Angeles to a fourth-place standing in the worst division in the majors? 

Of course the Dodgers have been a mess with the whole ownership debacle, but Mattingly’s team is just one game ahead of last-place San Diego and 11 back of the first-place Giants. L.A. is just 26-36 (.419) when playing any team not in their horrendous division this year. 

13. Lloyd McClendon

The base-stealing (literally) fireplug was certainly fun to watch manage, as the fans knew that an explosion was imminent whenever McClendon was in the dugout. The problem was that his teams rarely won.

McClendon managed to finish in fourth place in the NL Central in 2002 and 2003, winning 72 and 75 games in those seasons. But he closed out his managerial career with a 127-170 (.428) whimper, getting fired in the midst of a 2005 campaign that saw Pittsburgh finish last in its six-team division.

12. Mike Quade

The Cubs only have the Astros to thank for not being the worst team in baseball in the first half of this 2011 season. They are a pitiful 37-55 (.402) with no signs that Mike Quade can turn things around.

Quade has made many questionable on-the-field decisions this season, and that has carried over into the dugout with his public blowup with Ryan Dempster, one of the team leaders. His 24-13 record at the end of last year’s mop-up duty has seemingly been long forgotten by fans and Chicago media.

11. Bob Geren

Many people assumed Geren got the manager job in Oakland simply because he was the best man at GM Billy Beane’s wedding. But he certainly was not the best man in former A’s closer Huston Street’s eyes.

Street told the San Francisco Chronicle that, "Bob was never good at communication, and I don't want to speak for anybody else, but it was a sentiment reflected in many conversations during the two years I spent in Oakland," Street said to the Chronicle. "And even recently when talking to guys after I left. For me personally, he was my least favorite person I have ever encountered in sports from age 6 to 27.”

Geren was never able to get his team above .500 for a season, but he did come awfully close in 2010, going 81-81. In four-plus seasons in Oakland, Geren finished 334-376 (.470).

10. Larry Rothschild

He was on the receiving end of one of the quicker managerial hooks in major league history when he was canned after just 14 games of the 2001 season.

Some may think its unfair to dub a person as a terrible manager when the only team he had was an expansion Tampa Bay team playing in the same division as the Red Sox and Yankees. But Rothschild failed to reach 70 wins in any of his three seasons, and the Devil Rays were willing to spend money, but just on a bunch of past-their-prime power hitters like Jose Canseco, Vinny Castilla and Greg Vaughn.

Rothschild finished with a 205-294 mark (.411) finishing in the AL East cellar in all four of his seasons.

9. Roy Hartsfield

Most of you readers probably have no idea who Hartsfield was, but he has to make this list based on his .343 winning percentage in three seasons with Toronto from 1977-1979. The 166-318 record included three seasons of less than 60 wins, or three straight 100-loss campaigns, whatever you prefer. This was the lowest winning percentage of any MLB manager since 1970 with a minimum of 320 games.

Hartsfield died on January 15, 2011 at the age of 85.

Photo via cbc.ca.

8. Lee Elia

He will best be remembered for his Chicago Cubs press conference tirade from April 29, 1983, in which he bashed Cubs fans booing his team that started out 5-14. (Warning: The video has very offensive content.)

As funny as the tirade is, Elia’s managerial record was more comical to his detractors. In two seasons in Chicago (1982-83) and two more with Philadelphia (1987-88), Elia was 238-300 (.442) never finishing better than fourth place. He only finished a season with one winning record, and just barely, going 51-50 to close out the 1987 season.

7. Cecil Cooper

The lovable “Coop” actually won 86 games for Houston in 2008, but fell out of favor with Astros fans right around May 20, 2009 when he submitted the wrong lineup card. Michael Bourn singled to lead off the game, but the lineup card Cooper submitted to the umpire and his opponent, Milwaukee, listed Kaz Matsui batting first, turning Bourn’s single into an out for batting out of order.

Although Houston was able to win that game, Cooper was unable to keep his job for the remainder of the season, as he was canned after getting swept in Milwaukee on Sept. 20, leaving Cooper with seven straight losses to finalize his managerial career, that ended up 171-170.

6. Phil Regan

The “Vulture” replaced beloved ousted manager Johnny Oates in 1995, but he only lasted one year, finishing 71-73 in 1995 with Baltimore. Although two games under .500 would make Orioles fans rejoice these days, consider that the O’s were picked by many to win the pennant that year, and they made the playoffs promptly after Regan was rightfully canned, winning the Wild Card in 1996 and claiming the AL East title in 1997.

Regan was a stubborn skipper, refusing to move Bret “Jillian’s ex” Barberie and 36-year-old Kevin Bass from the top of the order. Barberie batted .241 with a .325 slugging pct, while Bass had a .303 on-base percentage and slugged .336 in his 111 games under Regan.

Despite a roster with some of the premier RBI men in the game (Cal Ripken, Rafael Palmeiro, Harold Baines and Bobby Bonilla), the “Killer B’s” scored just 32 runs apiece in a combined 615 plate appearances. Regan has never come close to managing another major league team.

5. Terry Bevington

There were certainly less successful managers in the history of major league baseball than Bevington, who was 222-214 in two-and-a-half seasons with the Chicago White Sox from 1995-97. By the end of his tenure, he had managed to become disliked by the fans, media, his fellow coaches and most importantly, his players—most notably, Frank Thomas.

But what puts Bevington on this list is a simple yet memorable gaffe that will live in baseball infamy. As he strolled to the mound to change pitchers, he calmly signaled to the bullpen, which wasn’t a real smart move considering he forgot to warm up any of his pitchers.

Bevington’s last known managerial address was in 2006 when he was the skipper for the Edmonton Cracker-Cats of the North American baseball league. He quit shortly after being suspended as part of a bench-clearing brawl.

4. Stump Merrill

He replaced Bucky Dent as Yankees manager on June 6, 1990 and quickly preceded to lose his first four contests. He would then post seven more losing streaks of four-plus games for the remainder of the ’90 season in which the Bombers lost a total of 95 games and finished seventh in the seven-team American League East.

This marked the first time that the Yankees finished in the basement since 1966.

Merrill somehow retained his job in 1991, and led the Yanks to a 71-91 mark, placing fifth in the division. That prompted an offseason firing and left Merrill with a record of 120-155 (.436) as a New York Yankee skipper. 

Photo via sulekha.com.

3. Al Pedrique

He certainly wasn’t put in a favorable position when he took over the Arizona Diamondbacks in 2004, but Pedrique was simply awful. Bob Brenly had “led” this once-proud franchise to a 29-50 record before Pedrique took the reins on July 2. The D-Backs faithful thought this change had to improve the ballclub, which had lost 11 straight games from June 18-29. 

They thought wrong.

Arizona dropped 19 of its first 21 games under its new skipper, finishing with a July record of 5-23. Pedrique suffered three more long losing streaks of six, seven and nine games, and wound up with a putrid 22-61 (.265) record as the manager. The D-Backs lost 111 games that year, which is still the most the National League has seen since the 1962 Mets went 40-120 in their inaugural season.

2. Alan Trammell

Trammell was an excellent player with Detroit, making six All-Star teams and forming a potent double-play combo with “Sweet” Lou Whitaker to help Detroit win the 1984 World Series. Unfortunately, that success didn’t translate to managing the team.

Trammell lost an American League record 119 games in 2003. Somehow he kept his job for two more years (maybe due to 2,365 hits as a Tigers player), and although the team improved by nearly 30 wins in 2004, Trammell’s three-year record finished with exactly 300 losses (186-300, .383).

1. Buddy Bell

Bell wasn’t just bad with one organization; he stunk up the joint with three different franchises in his managerial career. He posted identical .399 winning percentages in two-and-a-half years with Detroit (184-277) and in two-and-a-half seasons with Kansas City (174-262). His lone winning season was a 82-80 year in 2000 with Colorado.

In parts of nine major league campaigns, Bell finished in last place in his division six times, and never finished above third place.

Despite being an All-Star five times and winning six Gold Gloves, Bell was never involved in any postseason contests. That includes 1,243 games as a manager and 2,405 games as player, equaling a record total of 3,648 playoff-less games he was involved in during his major league existence.