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.

After more than 15 years paying his dues in baseball operations at both the major and minor league levels, Walt Jocketty wanted to become a general manager. He came close four times before finally landing the job in October 1994 with the Cardinals, a club that hadn’t made the postseason since 1987. In his thirteen years in St. Louis Jocketty’s Cardinals made it to the NLCS six times, winning two pennants and one World Series championship. After moving on to Cincinnati in 2008, Jocketty brought the Reds multiple postseason appearances, their first since 1995.

With a player’s strike in full swing when he was first hired, Jocketty could not immediately begin reconstructing his team, but he was used to operating under hardship. With the penurious A’s in 1980, during Charlie Finley’s final year of ownership, Jocketty ran the amateur draft without scouts–he relied on the major league scouting bureau for player information, and on his wife and a visiting clubhouse man for help keeping him on track. Despite the bizarre working conditions in Oakland, Jocketty long considered manager Billy Martin a mentor.

Jocketty remained ambivalent towards the influx of analytics despite spending many years in the Oakland front office with Sandy Alderson. His style combined the best of a commitment to scouting and an aggressive approach to team building. He was a master when it came to bolstering his team with a midseason trade, landing Mark McGwire (1997), Will Clark (2000), Mike Timlin (2000), Woody Williams (2001), Chuck Finley (2002), Scott Rolen (2002 and 2009), Sterling Hitchcock (2003), Larry Walker (2004), and Jeff Weaver (2006). He was not afraid to use his prospects in trade—generally receiving more value than the prospects turned out to be worth—and successfully restocked teams by acquiring mid-level free agents and trade targets on a regular basis. One of the very few GMs to make this latter strategy work, Jocketty possessed a knack for sensing which players still had something left and not getting stuck with bad contracts in trades.

When St. Louis started slowly in 1995, Jocketty fired manager Joe Torre 47 games into the season. For 1996 he brought in Tony LaRussa, his longtime friend from their years in Oakland. In addition, he delivered to LaRussa a number of offseason acquisitions that worked out surprisingly well. Jocketty secured closer Dennis Eckersley and starter Todd Stottlemyre from his old colleagues in Oakland, and signed Andy Benes as a free agent to strengthen his pitching corps. Two free agents, Ron Gant and an aging Gary Gaetti, proved valuable additions, and starting shortstop Royce Clayton came over in a trade. The Cardinals won 88 games before eventually losing in the NLCS.

Despite picking up Mark McGwire at the trade deadline in 1997, the Cardinals fell back over the next few years. But once again Jocketty struck it rich: in 1999/2000 he boasted one of the greatest offseason hauls of all time. In trades he obtained 2000 20-game winner Darryl Kile, 15-game winner Pat Hentgen, closer Dave Veres, center fielder Jim Edmonds, second baseman Fernando Vina, and shortstop Edgar Renteria. Jocketty also signed catcher Mike Matheny as a free agent. The Cardinals once again made it back to the NLCS before falling to the Mets.

The Cardinals returned to the postseason in 2001 and 2002, augmented with 1999 draftee Albert Pujols and the emergence of 1995 draftee Matt Morris, but still couldn’t get past the LCS. After missing the playoffs in 2003, Jocketty again went to work. He strengthened the pitching staff by swapping J.D. Drew for Jason Marquis and Adam Wainwright, signing free agent Jeff Suppan, and enjoying the recovery of Chris Carpenter, signed as a free agent a year earlier. Free agent signee Reggie Sanders and trade acquisition Tony Womack both won starting jobs and performed capably. The team won 105 games, their most since World War II, and finally captured the pennant before being swept by the Red Sox in the World Series. For his wheeling and dealing Jocketty was named the Sporting News Executive of the Year for the second time, having also won in 2000.

After winning 100 games the next year and again losing in the NLCS, the Cardinals fell to 83-78 in 2006, but it was enough to win a weak NL Central. Somewhat surprisingly, this team went on to win the World Series with the lowest winning percentage in history to win it. After falling short with some great teams, Jocketty had his world championship with one of his least accomplished ones.

The team missed the postseason in 2007 for only the second time since 2000, but owner Bill DeWitt was growing concerned over the tension within the front office. A year earlier he had promoted Jeff Luhnow–hired in the aftermath of Moneyball to bring a more analytical mind set to the Cardinals and beef up the team’s international presence and amateur drafting–to run the farm system in addition to the draft. Jocketty was clearly unhappy with this internal reorganization and his loss of authority, and DeWitt decided the team should move on without him.

Jocketty didn’t have to wait long for his next opportunity. Cincinnati owner Bob Castellini knew and respected Jocketty from his days as a minority investor with DeWitt in St. Louis. In January 2008 he brought in Jocketty as a special advisor and in April made him general manager. Jocketty inherited a team that had not finished above .500 since 2000, but was not without talent, including Joey Votto, Brandon Phillips, Jay Bruce, Johnny Cueto, and Bronson Arroyo. Jocketty spent most of 2008 evaluating his club, which was close to competing. Over the next couple of years Jocketty added Jonny Gomes, Ramon Hernandez, Orlando Cabrera, and Scott Rolen via trade or free agency, flame throwing Aroldis Chapman from Cuba, and Mike Leake, drafted in 2009 as major league-ready hurler. In 2010 the team won the division title for the first time since 1995 but lost in the NLDS. Jocketty won the Sporting News Executive of the Year for the third time (joining Branch Rickey and George Weiss as the only executives to have won it at least three times).

Jocketty continued to fine-tune his squad, adding free agent Ryan Ludwick and trade acquisition Mat Latos (at the cost of two first round draftees) for 2012 and Shin-Soo Choo for 2013. The Reds qualified for the postseason both years. They had become overly dependent on their stars for offense, however. When Choo left as a free agent and Votto, Phillips, and Bruce suffered through injury marred seasons in 2014, the Reds fell back to 76 wins.

Jocketty has always relied on his ability to identify still productive, moderately-priced, mid-career major leaguers, and he is one of the very few GMs to have successfully pulled this strategy off. It helps of course to have one’s farm system deliver an Albert Pujols, but the Reds have a farm system deep in pitching and there is no reason to think that if the high-priced Reds core returns healthy in 2015, Jocketty won’t again be able to find quality short term solutions to keep the team competitive.

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.