This post is part of a series in which Mark Armour and I count down the 25 best GMs in history, crossposting from our blog. For an explanation, please see this post.

[This one is from Mark]

Harry Dalton was the GM for three teams over a 25 year period, winning five pennants and contending for several others. His claim to fame was his work in Baltimore, where he made a series of moves to turn a very good team into one of the greatest ever assembled.

When Dalton went to work for the Orioles in late 1953, he was a 25-year-old Amherst grad just back from serving in Korea. He spent the next seven years working as a key lieutenant for farm director Jim McLaughlin. Though the Orioles organization made progress in the 1950s, things might have gone better without the ongoing battle between McLaughlin and manager/GM Paul Richards, each with his own autonomous scouting staff. Richards relinquished his GM duties to Lee MacPhail in 1958, and by 1961 both Richards and McLaughlin were gone. MacPhail promoted Dalton to run an extraordinarily productive farm system. Dalton’s talented team of scouts became known as “The Dalton Gang,” and his organization included legendary coaches and instructors like Earl Weaver and Cal Ripken, Sr. After the 1965 season MacPhail left to work in the commissioner’s office, and Dalton became general manager.

The Orioles had been a good team for several years by this time, winning 97 and 94 games the previous two seasons. MacPhail’s last act was to work out a trade with the Reds that would land Frank Robinson. He left approval of the deal to Dalton, who tried to extract another piece from Reds GM Bill DeWitt. DeWitt balked, but Dalton sensibly chose to authorize the deal in its original form. Robinson became the leader of the team, and won the Triple Crown and MVP while he was at it. The Orioles won the 1966 World Series.

The Orioles fell back in 1967, largely due to injuries to Robinson, Jim Palmer and Dave McNally. When the club failed to rebound adequately in 1968, reaching the All-Star break at 43-37, Dalton fired manager Hank Bauer and gave the job to Earl Weaver, who had spent many years in the organization as a Minor League manager. Weaver was not shy about making changes, playing Don Buford (a great Dalton acquisition) and Ellie Hendricks, and taught the Oriole Way that Dalton had long championed in the minors.

After the 1968 season Dalton traded outfielder Curt Blefary to Houston for pitcher Mike Cuellar, who won 125 games over the next six seasons. The next three years the Orioles won over 100 games, waltzed to division titles, and swept the ALCS. That they only were able to win one World Series masked how great this team was. So good, in fact, that Dalton only had to make one trade of note — he dealt some unneeded players to the Padres for Pat Dobson, who won 20 games in 1971. In six years Dalton won four pennants and two World Series in Baltimore.

After the 1971 season Dalton left the Orioles and took a job as GM of the Angels. The difference in the situations could hardly have been larger — the Angels had just come off a fourth place finish on the field and a much worse one off of it. Picked to win the AL West by many pundits, they endured the emotional breakdown of their defending batting champ, Alex Johnson, the breakdown and retirement of newly acquired slugger Tony Conigliaro, a gun confrontation in the clubhouse, additional turmoil between teammates, and more. Not surprisingly, the manager and general manager both lost their jobs. Owner Gene Autry hired Dalton to straighten it all out.

A few weeks after taking over, Dalton traded the longtime face of the franchise, Jim Fregosi, to the Mets for four players. One of the players, Nolan Ryan, became a star, making this the best trade in team history. Unfortunately, this proved to be the high water mark of his six years in Anaheim. A year later he made another big deal, trading star pitcher Andy Messersmith to the Dodgers for Frank Robinson (returning to the AL to utilize the new DH rule), pitcher Bill Singer (who would win 20 games the next season), and Bobby Valentine. The key to the deal for Dalton was Valentine, a talented 22-year-old who could hit, run and play centerfield. Unfortunately, in May 1973 Valentine tore up his knee on Anaheim’s chain link fence trying to catch a fly ball. He never recovered his former speed, and never fulfilled the promise many had for him.

Dalton continued to make deals, but he just never really had enough talent. The team had drafted Frank Tanana in 1971, and a few years later he and Ryan were their best two players. The only impact player drafted on Dalton’s watch was Carney Lansford, who did not help until Dalton had left. Desperate for offense, in late 1975 he traded Ed Figueroa and Mickey Rivers for Bobby Bonds, in what turned into a great deal for the Yankees. Bonds had a great year for the Angels in 1977 before he moved to his next stop.

With the advent of free agency in 1976 Autry was ready to go all-in, and Dalton made an unappreciated, canny move. The rules in the first year of free agency stipulated that a team could only sign two players, unless they lost more than two themselves, in which case they could sign as many as they lost. The Angels played the 1976 season with two unsigned players: seldom used utility men Paul Dade and Billy Smith. On September 9, the Angels purchased infielder Tim Nordbrook from the Orioles, an unusual transaction for a team that was in fifth place. What made this deal interesting was that Nordbrook was also soon to be a free agent, giving the Angels a total of three. The Angels made no effort to sign Nordbrook, so they ultimately “lost” three players who combined for 25 at bats and 4 hits in the 1976 season. Having lost three players, Dalton was able to sign Don Baylor, Joe Rudi, and Bobby Grich.

The Angels looked to be a contender for 1977, but Rudi and Grich both got hurt and the team stumbled to fifth place. Rudi was through, but Grich recovered to continue his great career the next season. Too late for Dalton, who left after the season to become GM of the Brewers. Dalton likely could have stayed on, but he was unhappy when Autry hired Buzzy Bavasi to be team president, Dalton’s boss. When Bud Selig offered him the job in Milwaukee, Dalton was assured that he would be in charge. The squad he left behind in California would capture its first division title two years later.

In Milwaukee, Dalton inherited some talent: Robin Yount, Cecil Cooper, Sixto Lezcano, and Paul Molitor (who would debut in 1978). That said, the team had won 67 games in 1977, and had not finished .500 in their nine-year history. That would change quickly as the Brewers won 93 games in 1978, advanced to the playoffs in 1981 and to the World Series in 1982. The six-year period from 1978 to 1983 remains the best in Brewers history.

Dalton made some good moves to get this team over the hump and keep it there. He traded for Buck Martinez and Ben Oglivie soon after he arrived. He made a huge deal in December 1980 with the Cardinals, landing Rollie Fingers and Pete Vukovich (who between them won the next two Cy Young Awards), and catcher Ted Simmons, their new cleanup hitter.

After a few down years, the Brewers came back to contention in the late 1980s with a new team centered around Molitor and Yount, plus players Dalton’s staff had signed or drafted, like Teddy Higuera, BJ Surhoff, and Chris Bosio. Milwaukee won 91 games in 1987 and finished just two games back in 1988 but failed to get back to the post-season. Dalton was released from his contract after the 1991 season after 14 years in charge.

That Dalton was not able to repeat his Baltimore success in his next two stops is not surprising — his Oriole squads were among the best teams ever, a team he helped put together in the minor leagues and helped turn into a juggernaut as the GM. He inherited a mess with the Angels, and while he improved the talent level, he was not able to win the division. In Milwaukee he had more talent to work with and he made some key additions that helped the Brewers capture their only pennant.

To read more about the history of baseball operations and the GM, please buy our new book In Pursuit of Pennants–Baseball Operations from Deadball to Moneyball via the publisher or at your favorite on-line store.