Year: 2010

As Philadelphia prepares to present Ruben Amaro, Jr. with his weight in cheesesteaks, it is important to remember that for all of the Phillies' 10,000+ losses, Amaro's got some worthy competition among the GMs in Philadelphia history.

Indeed despite the acquisition of Cliff Lee this week, much of Amaro's story is still to be told. As of this writing, it isn't clear Amaro is in the top three to hold that executive position. Here are the cases for the best five since 1960. I'm using the 50-year window, with the clear understanding that whoever traded Bill Foxen for Fred Luderus, thus securing the first baseman on the NL Champion 1915 team, was a baseball genius.

1. Paul Owens (1972-1983): Owens took the reins of a team that went 59-97 in 1972, and whose primary achievement was to allow Steve Carlton to display his brilliance by winning so little when he didn't pitch (Carlton won 27 games). But by 1975, the Phillies were contenders, and by 1976, they won 101 games, beginning an eight-year stretch that included six playoff appearances, two NL pennants and a World Series title in 1980.

Interestingly, his predecessor, John Quinn, helped him quite a bit, trading Rick Wise for Carlton just months before Owens took over. Owens had directed Philadelphia's farm system before his promotion, and even on the 1972 team, those efforts began to pay off. A 21-year-old Greg Luzinski hit 18 home runs, a rookie catcher named Bob Boone hit .275, and a second baseman/third baseman named Mike Schmidt hit his first major league home run.

But while Owens had a head start, he only built upon those gains in subsequent seasons. His drafts produced talent like Lonnie Smith and Ryne Sandberg, while he signed George Bell and Julio Franco as amateur free agents. He traded Willie Montanez for Garry Maddox. Both men hit  at about league average rates, but Maddox played an elite defensive center field.

Owens didn't put together a great Rule 5 track record – he lost Bell, Greg Walker and Willie Hernandez in various Rule 5 drafts. He also, near the end of his tenure, traded five players, including Franco, for Von Hayes, and five days later, traded a package including Mark Davis and Mike Krukow to the San Francisco Giants for reliever Al Holland and an aging Joe Morgan. But because of what he did well, Owens is still the easy choice at number one.

2. Pat Gillick (2005-2008): Simply put, it is hard to argue with the results. Gillick succeeded everywhere he went, and in just his second season with Philadelphia, the Phillies won the National League East. In his third season, they won a World Series.

So what did he do to push beyond the successful, but also-ran teams of Ed Wade? For one thing, he immediately traded Jim Thome to open first base to a young Ryan Howard. He put together drafts that allowed Philadelphia to deal prospects to fill remaining holes (see Kyle Drabek, for instance, who eventually headlined the deal for Roy Halladay). He picked up Jamie Moyer for a couple of minor leaguers, signed Jayson Werth for six fewer years and approximately $125MM fewer dollars than the Nationals. Plus, he dealt Michael Bourn for Brad Lidge.

Not everything worked for Gillick – his trade of Gio Gonzalez and Gavin Floyd for Freddy Garcia was one-sided for the White Sox. On the other hand, Gonzalez and Floyd would be battling for the fifth starter's job on the 2011 Phillies.

In short, enough of what Gillick did worked, and following the 2008 season he handed a team over to Amaro that managed to win another NL pennant with little tweaking. Only his relatively short tenure keeps Gillick from the number one spot.

3. Ed Wade (1998-2005): I'll be honest: even I'm surprised to see Wade this high. But hear me out.

Wade's drafts, unquestionably, formed the heart of the championship years Philadelphia celebrated after Wade left. Ryan Howard, Chase Utley, Cole Hamels, Pat Burrell, Ryan Madson, Brett Myers, Kyle Kendrick, even the eventually-traded Gavin Floyd, J.A. Happ and Michael Bourn were drafted and signed under Wade. Carlos Ruiz and Antonio Bastardo signed as amateur free agents.

To be sure, there were missteps. Curt Schilling, traded to Arizona, yielded Travis Lee as the primary piece in return. Nick Punto and Carlos Silva went to Minnesota in exchange for Eric Milton. Free agent relievers like Terry Adams too frequently found multi-year deals, thanks to Wade. And despite contending much of the time, Wade couldn't add enough talent to get Philadelphia over the finish line first.

But the Phillies won at least 86 games in four of Wade's final five seasons at the helm, then began a string of four consecutive NL East titles with mostly Wade-acquired players two years later. Most GMs don't get fired for results like this; they get raises.

4. Ruben Amaro, Jr. (2008-Present): Well, for the most part, you probably already know about the successes. Amaro acquired Halladay. He just signed, in an under-the-radar story, Cliff Lee. He acquired Roy Oswalt for surprisingly little this past summer. And under his watch, the Phillies have two playoff appearances, including one NL pennant.

Why isn't Amaro higher? Two reasons. One is, as demonstrated above, his two teams have won largely on the efforts of his two predecessors. Not entirely, of course, but quite a bit. And beyond the big three pitchers mentioned above – two of whom, it must be said, were acquired with prospects provided by his predecessors, there are some troublesome moves as well.

Many of the deals Amaro has given out already look like mistakes. Three years and more than $30MM to Raul Ibanez before 2009 has proven to be an overpay since June of 2009. Three years and $24MM to Joe Blanton has Philadelphia trying to dump Blanton's salary a season later. And the five-year, $125MM deal signed by Ryan Howard – one that doesn't even kick in until 2012 – is arguably the inexplicable move of the baseball decade.

As the players Amaro inherited age, it will be fascinating to see how well the team plays. If he manages that transition well, he'll certainly move up on this list. But the long-term deals he's given out to many older players could keep him anchored at fourth.

5. John Quinn (1959-1972)/Lee Thomas (1988-1997)

This is a very difficult decision, so I've elected not to make it, and call it a tie. Quinn, as mentioned before, made the Steve Carlton trade. He signed Dick Allen as an amateur free agent. But he also presided over seven losing seasons, and never did get Philadelphia to the postseason.

As for Thomas, he took over a 67-win team in 1989, and by 1993, led them to 97 wins and a NL pennant. He stole Dave Hollins in the Rule 5 draft, brought in Lenny Dykstra and Roger McDowell for Juan Samuel, and managed to trade Jason Grimsley for Curt Schilling. And yet, Thomas' Phillies didn't post a winning record once in his final four seasons as GM, meaning his teams had one winning record in eight years.

Both men made some astute moves while GM. But Phillies fans are equally glad that Quinn made way for Owens, and Thomas made way for Wade, Gillick and Amaro.