How can we fairly evaluate general managers in baseball?  Certainly, some function of wins divided by payroll gives us a pretty good idea of who is doing his job and who is ruining his franchise.  But we do need to look beyond only that.  How have his trades panned out?  What kind of shape is his farm system in?  How many players has he overpaid, and how many is he robbing blind?

I attempt to take these factors into account as I rank the five best and five worst general managers who were active this season.

Top Five

1. John Schuerholz

The contrarian in me wants to point out that the Braves' "consecutive" pennant titles streak has now come to an end for two straight years after pitching coach Leo Mazzone left the organization.  The picture of Schuerholz is not complete, however, until you look at what happened to the Kansas City Royals organization when Schuerholz left in 1990.  Both the Royals and Braves organizations have fared much, much better with Schuerholz in the captain's chair.

Even though the Braves have enjoyed some top-tier salaries lately, no other GM can match Schuerholz' track record.  He rarely makes a bad trade, does extremely well in drafts, and does not throw money at overpriced free agents.  As much talent as he gave up in the Mark Teixeira deal, you pretty much have to give Schuerholz the benefit of the doubt in these kinds of trades at this point.

If a front office executive ever makes it into the Pro Baseball Hall of Fame, John Schuerholz should be the pioneer.

2. Terry Ryan

Just days ago, Terry Ryan announced that he would step down as the Twins' general manager, though stay on as a senior advisor to the organization.  Ryan would have likely usurped Schuerholz from his top spot in a few years had he not made this move.  But being a baseball GM is undoubtedly a draining job, and the fact that John Schuerholz has handled the grind for nearly 30 years while Ryan could only do it for half that time must be a factor when we consider their greatness.

In fact, the beginning of Ryan's tenure in Minnesota was spotty.  Faced with a miniscule payroll and apathetic fan base, he was unable to get the Twins even to 3rd place in the first seven years he managed.  Then, as though he took Bud Selig's empty threat of contraction personally, Ryan transformed into the best GM in baseball over the next seven years of his tenure, even when you factor in his letting David Ortiz go to Boston.  His career as a GM is a metaphor for the typical Johan Santana season.

Did I say Johan Santana?  He's the guy Ryan got with cash in return for Jared Camp.  Ryan was smart enough to limit Santana's use for his first four seasons, even though the Twins very competitive for three of those. You've probably heard of the Joe Nathan, Francisco Liriano, and Boof Bonser for AJ Pierzynki swap he orchestrated with Brian Sabean of the Giants.  We don't even know the full extent of the damage to Sabean's backside on that one, yet.

Ultimately, he and Billy Beane are the two GMs that come up in a discussion of front office guys doing the most with low payrolls.  Ryan took longer to get rolling, but has been better of late.  We should never forget just how unbelievable the Twins Phoenix-like 2006 season was, and just how much Terry Ryan had to do with it.      

3. Billy Beane

What more can we say about Billy Beane?  Five of the eight instances of a bottom-10 payroll team making the postseason from 1996 through 2006 came courtesy of his Oakland Athletics.  They have a well-stocked system in the upper levels, and they are spinning retreads like Jack Cust into stars.  Probably the main reasons that I don't rank Beane  higher are the two gaps I see.  The two-year gap now where the A's will not finish over .500 and the gap coming 5-10 years from now.  Beane did not follow his own advice in the past few drafts, selecting high school pitchers all over the place and getting burned.  As a result, the lower levels of the Oakland system are threadbare, and Beane is going to need to swindle the Royals something fierce to overcome it.

4. Josh Byrnes

The Arizona Diamondbacks franchise was in utter shambles when Josh Byrnes took over after the conclusion of the 2005 season.  The team was coming off back-to back losing seasons for the first time in franchise history, they were still paying backloaded contracts to players who hadn't played there in years, and worst of all, Russ Ortiz still had $23 M left on his I-make-Darren-Dreifort-look-like-a-bargain contract.

But Byrnes built arguably the best farm system east of Los Angeles and had enough faith in it to shed several burdensome contracts (Shawn Green) and play his young guys.  When his second best pitcher demanded a trade and would not allow a trade to a west coast team, Byrnes was rather handcuffed.  But he was still able to get decent value for Javier Vazquez in Chris Young, Luis Vizcaino, and Orlando Hernandez.

If you shot Vince Coleman in the leg, he could probably still outrun a lot of baseball players.  Josh Byrnes was hit by a barrage of bullets as soon as he agreed to take the Diamondbacks job, and his franchise is nevertheless beating nearly every other franchise in baseball, both at present and for the future.  The only reason Byrnes does not rank higher is because he has been at this for less than two years now, where the guys ahead of him have been at it for ages. 

5. Mark Shapiro

When Shapiro took over for John Hart in 2002, the Indians' payroll had already begun to plummet.  Their 2001 payroll of over $93 M dropped to just under $79 M in 2002, then to $48.6 M in 2003.  Their opening day payroll of $61.6 M this year is easily the highest that the team has had since. 

While many would chastise Mark Shapiro for turning a perennial division-winner into a middle-of-the-pack team, I look to history to look to the future.  Meaning, the historically inept Indians were able to succeed in the mid-90's by developing good young players and signing them to long-term contracts (before they even became arbitration eligible in many cases).  Albert Belle, Kenny Lofton, Carlos Baerga, Charles Nagy, Jim Thome, and Manny Ramirez became the underpaid nucleus of a dynasty.

It doesn't take Nostradamus to see that the exact same thing is happening in Cleveland now.  Jhonny Peralta makes just $2.25 M next year, and is signed through 2011.  Grady Sizemore makes $3 M next year and his contract runs through 2012.  Victor Martinez - $4.24M/2010.  Travis Hafner - $8M/2013.  C.C. Sabathia is going to make record free agent money after netting $8 million in 2008, but the Tribe has the likes of Fausto Carmona and Adam Miller ready to take over for the big guy.

Whether you look at the short term or the distant future, the Indians look like they are going to compete every single year.  If Shapiro is then afforded the same freedom as his predecessor was, he will be able to supplement this nucleus with imports a la Roberto Alomar, Matt Williams, and Davis Justice. 

Few teams can succeed year in and year out with a small market budget.  The Indians seem to prefer going on intermittent eight-year stretches of dominance rather than putting forward a pretty good team every year.  To each their own.       

Bottom Five

1. Whoever the heck is running the Orioles

From what I can piece together, Syd thrift was fired as the Orioles' GM in 2003 and replaced with a two-headed monster of former pitchers Jim Beattie and Mike Flanagan.  In 2006, Jim Duquette (who had a wildly successful 1-year tenure as the Mets' GM in 2004) replaced Beattie, but it was supposedly made clear that Duquette was to report to Flanagan, rather than continue with the GM-by-committee approach.  This June, Andy MacPhail entered into the mix, but the current hierarchy remains unclear to me.

But it appears that in one fashion or another, Mike Flanagan has been at the center of it all.  So this ranking is directed at him.

Dear Mike,

What a great playing career you had!  It must have been great working under Earl Weaver and alongside so many similarly talented teammates.  There can't be too many players out there who did not experience a losing season until their 12th year in the league.

I do, however, find it odd that in all of your time surrounded by an ambiance of winning that none of it rubbed off on you during your front office tenure.  I look at the contracts that you gave Melvin Mora, Ramon Hernandez, Danys Baez, Jay Gibbons, Jay Payton, and Aubrey Huff, and my eyes begin to water.  Trading John Maine for Kris Benson?  Makes me want to with my head on the wall.  Trading for Tools Patterson?  Well, that made my day, but only because I'm a Cubs fan.

I definitely like your acquisition of Leo Mazzone, although it might help if you hired some trainers that could keep your pitching staff healthy, as there's probably only so much Leo can do with torn elbows and shoulders.  And it's entirely possible that your first-round draft choice in 2003, Nick Markakis, is on his way to a fine career.  But bottom line, your payroll this year is over $93 M, and you have arguably the worst team in baseball, with no help for the future on the immediate horizon.

Congratulations, you are the worst general manager (or whatever it is you call yourself) who worked this year. 

Yours,

~Keith

PS- How come your teams never win games after July?  

2. David Littlefield

In one of the first articles I wrote for Baseball Evolution posited an alternate reality in which the Pittsburgh Pirates had the best pitching staff in baseball.  The catch was that in this reality, Pirates GM Dave Littlefield wasn't a blithering idiot.

Littlefield's failures weren't readily apparent to Pirates fans because he was still better than his predecessor, Cam Bonifay.  In the interest of space and time (uh-oh, I'm getting all Sci-Fi on you again, aren't I?) I will not bother to list all of Littlefield's failures as a GM.  Suffice it to say that Littlefield ran a small market team as though he had a large payroll to work with and vigorously outbid other teams for mediocre or worse veteran players rather than work on acquiring and developing young talent.  The Pirates went 442-581 during Littlefield's tenure, and are now enduring their 15th consecutive losing season.

3. Tim Purpura

It feels odd to list a GM here that took a team to its first ever World Series during his first year in charge.  However, most of the pieces for that 2005 team were already in place when Purpura took the helm. 

Even if you want to give Purpura some of the credit for that success, it probably doesn't outweigh the real possibility that the Astros franchise is currently in bigger trouble than any other major league franchise.  It will be burdened by Carlos Lee's contract for five more years, and generally speaking, the Astros are filled with declining players rather than improving ones. 

There is little help on the horizon, particularly with Purpura signing enough free agents to deprive the club of a first and second round pick in this year's draft, then failing to sign his third and fourth round selections.  The Astros appear poised to become the new Orioles - a team with high payroll and low success.     

4. Jim Hendry

Jim Hendry's legacy is quieting those fans who say that the Cubs do not want to win because they are cheap.  He has now proven without question that the Cubs can spend a lot of money and still not get results.  They are going to win the NL Central by default this year, but don't let that fool you into thinking that this is a well-run franchise.  The farm system doesn't even have the usual highly touted prospects that never develop well, with the exception of Jeff Samardzija, who is a prototype for that phenomenon.  Although the hometown discounts from Carlos Zambrano and Aramis Ramirez are helpful, the insane Soriano contract balances those out, and then you have a lot of marginal players on the wrong side of 30 who are still signed beyond this year (Jacque Jones, Scott Eyre, etc.).  If he is lucky, the Cubs will Cardinals their way to the World Series this year, and no one will care that the Cubs were bad before that and will continue to be bad after it.

5. Brian Sabean

Brian Sabean gets a lot of respect in some circles because of the tremendous success his Giants had in the first eight years of his tenure.  Personally, I think that this success was middling given that he was spotted the best baseball player since integration when he signed on to take the Giants job.  I mean, he hasn't exactly matched the Yankees' success with Ruth, has he.

Ah, but you say that those Yankees also had Lou Gehrig while the Giants did not.  But that is what everyone says.  That is the point.  After Jeff Kent left, WHY DIDN'T HE GET A GOOD HITTER TO BAT BEHIND BONDS?  The players who hit behind Bonds tend to have career years... so imagine what would happen if Sabean had put someone who could hit even better than Benito Santiago or Ryan Klesko there? OK, Moises Alou, but no one really didn't expect him to stay healthy, did they?

And don't tell me that Sabean couldn't afford to pay both Bonds and another star hitter.  He's spending plenty of money, just not on good hitters.  The trouble, I suppose, is that their top position player prospect, Kevin Frandsen, has the ceiling of a utility infielder.  And as Sabean has been there so long, he has no one to blame for the sad state of the farm system (A.J. Pierzynski trade).  Tim Lincecum was a nice pick, but we'll see what happens as the 23-year old approaches 200 innings pitched in the final weeks of a lost season.

I will close this section, and this article, with two words: Barry Zito.

See also: Gregory Pratt's rankings