If you want to classify the tenure of Jim Hendry as a Cubs executive, well, he definitely joins the ranks of nothing special or worse.

When we stop to think about the Hendry era, we sometimes don’t realize how far back it goes—all the way back to 1995 when he headed up the farm system, and to 2002 when he officially took over as GM. That’s a long time with very little tangible achievement. Sure, they won three division titles, but they have not built a perennial contender.

If I had to sum things up in a single thought, it would be, “OK at small-scale incremental changes, bad at big trades, big changes, worse at overall strategy and building a winning team.”

In other words, this guy is a tolerable small market leader and a failure at big market moves. To the extent the Cubs are a major market team—and you have to say that with their payroll and profitability, they cannot be considered anything else—Hendry is the wrong guy for the job.

Hendry was the major player in the minor league and scouting areas from 1995 until he became GM. So, as far as first round picks go, you’ve got Kerry Wood in ’95, Jon Garland in ’97, Corey Patterson in ’98, Mark Prior in ’01 and pretty much dreck until you get to Tyler Colvin in ’06.

Colvin is the first product of the Oneri Flieta/Tim Wilken era anyway, where player development efforts seem to have picked up. Garland was traded away for garbage. Throw in Dontrelle Willis, also traded away basically for the journeyman Matt Clement, and Carlos Zambrano and that’s pretty much it for the Hendry era. Maybe throw in Ricky Nolasco who was drafted in ’01 as well and similarly traded away for nothing.

Outside of the pitchers, there’s nothing much to write home about, and half of them were discarded. The system’s inability to produce position players with any consistency has been a notable failure. Lately, the Cubs have been able to promote a major league catcher in Soto and a good shortstop in Starlin Castro, but their much heralded prospects, guys like Felix Pie, for example, have fizzled.

I suppose on the strength of this performance, Hendry was promoted to GM in the middle of 2002, having pretty much served in that capacity for a little while before the formal announcement. The first move he made was to fire Don Baylor, a good move. He promptly hired the first of two celebrity managers, Dusty Baker in ’03 followed by Lou Piniella in ’07, both of whom enjoyed initial success and both of whom were run out of town at the end of their generous contracts.

Hendry made his best moves at the start of his GM career and has lost the magic as time passed.

He has always been pretty good at dumping toxic contracts, and one of his first moves was to somehow convince the Dodgers to take Todd Hundley off his hands in return for Mark Grudzielanek and Eric Karros, both of whom were on the downside of their careers, but both of whom played well for the Cubs in 2003 and helped a lot in what was, arguably, their best run in modern times.

Most of the rest of the ’03 team was in place when Hendry took the reins, i.e. Alou, Patterson and Sosa in the outfield, etc. The arrival of Prior and Zambrano as dominant starting pitchers carried the Cubs into early contention.

Hendry then pulled off the most spectacular trade of his life, and actually probably the only major trade he ever made that worked to the teams benefit, when he managed to pick up Aramis Ramirez, Kenny Lofton and Randall Simon from the Pirates more or less for nothing.

The following year, he picked up Derrick Lee in the offseason, also pretty much for nothing, probably his second best trade. He also let Lofton walk after the season, counting on Patterson returning to the level of play he displayed before his injury in 2003. This was a big mistake.

After that, I think it is fair to suggest that Hendry had seen his best days as GM recede behind him. The blockbuster deal at the 2004 trade deadline for Nomar Garciaparra was a bust. Nomar was hurt, and his career had already hit the skids.

After the Cubs fell apart at the end of 2004 and after the injuries to Wood and Prior, the remainder of Baker’s tenure as manager was a death march and Hendry was unable to do anything significant to stop it, other than holding on to Baker for the remainder of his contract even though it was obviously time to pull the plug.

Things changed radically beginning in 2007, when the Cubs dipped heavily into the high-end free agent market, mostly in a fairly successful attempt to inflate the resale value of the franchise while diminishing its value on the field. They picked up Ted Lilly and Jason Marquis to bolster their pitching, the Lilly signing being, overall, the only beneficial one.

Anyway, the real puzzler was signing Alfonso Soriano, a guy who really has no idea how to play baseball and never has, to an eight-year deal. There are still four years left on this deal at about $18 million per year. This alone would be cause for any respectable team to just fire their GM on the spot.

The team played pretty well, though, in 2007, and Piniella managed to cobble together a pretty decent run, dumping several useless cogs that Hendry had accumulated like Cesar Izturis and half-a-dozen second basemen in favor of home grown talents like Ryan Theriot. The signing of Mark De Rosa, a relatively minor acquisition at the time, helped immensely.

The following season, the Cubs went out and got Kosuke Fukudome for big bucks. I’ve never been one to fault Hendry for this signing. Everybody wanted Fukudome and projected him as a solid player. The Cubs are paying him too much money, but he is, at least in my view, rather an undervalued performer considered just on the basis of his skills and their value to a team that is consistently weak defensively and in terms of fundamentals.

The real plus moves that pushed the Cubs into contention, though, were once again small, and arguably lucky, choices, mainly the signing of Jim Edmonds and Reed Johnson, who turned out to be a surprisingly potent tandem in center field. That, and a career year for De Rosa, helped a lot.

During this same stretch, the Cubs gave lucrative extensions to Carlos Zambrano, Ryan Dempster, Derrick Lee and Aramis Ramirez. In all honesty, it is hard to argue with these decisions, however much in retrospect they may seem excessively generous. I’d probably have made the same moves under the same circumstances.

The really stupid signing came in ’09, when Hendry went out to get Milton Bradley as a left-handed bat even though he was always better as a right-handed hitter and he was a known nutcase. Everybody knows that story, but again Hendry did demonstrate a remarkable ability to exchange bad contracts and come up with something in return when he dealt Bradley to the Mariners for Carlos Silva.

What emerges from all this is the portrait of a GM who really does not have solid judgment most of the time and who seems to spend money foolishly and to no set purpose. The Cubs don’t really seem to have a plan in mind on the kind of team they want to create, nor any idea how good, consistent teams are built.

Just for comparison, look at the Phillies development through this same period when they had about the same or even slightly lower budgets and competed for pretty much the same pool of talent, especially in the free agent market.

The Phillies were more fortunate or more skillful in developing home-grown position players, bringing up Ryan Howard, Jimmy Rollins and Chase Utley through their own farm system and trading for young players like Jason Werth and Shawn Victorino. Their biggest weaknesses were 3B, LF and starting pitching.

They managed to cycle through free agents in LF and 3B and get the kind of production they needed. A good case in point was LF, when the Phils gave up on Pat Burrell and decided they needed a left-handed bat there. They signed Raul Ibanez. The Cubs, in the same position signed the abominable Milton Bradley, even though Ibanez was available at the time.

The Phillies decided to construct a balanced power-hitting team built around their ballpark. They also knew they would need exceptional pitching to overcome the inherent problems of playing in a stadium where cheap home runs were the norm, so they concentrated their efforts on acquiring really, really good pitchers, guys like Lee, Halladay and Oswalt, even if it meant giving up prospects to get them.

Now, contrast that same era with the Cubs, who seem to have had no obvious plan, who cannot seem to build a lineup that is balanced and makes sense, starting with the leadoff man, who do not seem to understand the strengths of their team or minor league system or the kind of team they need to build.

There are strong arguments for change at the top, which, of course, is not forthcoming. One may only hope, but without much confidence, that some lessons have been learned. Maybe Hendry can pull off a hat trick and dump Soriano in the same way he unloaded Hundley and Bradley. (Incidentally, I would take the rumored Soriano for Zito trade in a minute).

Maybe Hendry will look at the Giants as a model for rebuilding, which would not be a bad start.

Maybe pigs can fly.

Well, whatever. There is always next year.


The Ivy Covered Burial Ground

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