Baseball Prospectus’ Pre-season Projection: 88-74, second place
Current record: 66-87, fifth place

Mark Reynolds is historically relevant, but strikes out a great deal.

Buster Olney of’s Take

What went wrong: In short? Just about everything. Staff ace Brandon Webb made one start before requiring shoulder surgery, manager Bob Melvin was fired, center fielder Chris Young struggled so badly he was sent to the minor leagues, and Eric Byrnes-a player the team kept instead of Carlos Quentin-gave the D’backs almost no return (again) on his $11 million salary. Plus, they had an assortment of other injuries. Plus (!) they had to lay off some members of the organization. There’s no way to sugarcoat it: this was just a brutal year for Arizona.

Biggest puzzler on the drawing board: Webb has a club option for $8.5 million for 2010, and given that he went 22-7 with a 3.30 ERA in 2008, it would seem to be a no-brainer for Arizona to pick it up. But the Diamondbacks are not really well-suited for risk; they had a payroll of about $70 million this year, and if they were to be at about the same level in 2010, that would mean almost 30 percent of their budget would be tied to two guys (Byrnes and Webb) who might give them almost nothing if they suffer setbacks in their respective rehabs. Webb made it clear in a recent interview with The Arizona Republic that he is not interested in some negotiated restructuring of his option year, so the Diamondbacks face a very difficult choice: keep Webb and his surgically repaired shoulder, or let him walk away and assure themselves of better financial flexibility. They have to inform Webb of their decision within five days after the World Series ends.

The Baseball Prospectus Take

The 2009 Diamondbacks serve as the perfect example of how Murphy’s Law-what can go wrong will go wrong-can drastically transform team performance. The Snakes expected to build off of their experiences over the past two seasons and once again contend for a playoff berth, relying on a solid starting rotation, a decent bullpen and a young-but-potent nucleus of hitters. Instead, Webb made a poor Opening Day start… and then missed the rest of the season. The bullpen imploded. Young continued to spit in the face of PECOTA‘s optimism about him. The team’s defense faltered (Arizona had committed 122 errors through Thursday, second-most in the majors, including a team-record 26 by outfielders and 19 by pitchers). Those who analyze risk management may have expected one or two of these events to occur, but not all of them in the same season. Regardless, the Diamondbacks have several bright spots, and are not as poor as a 66-87 record would suggest in a vacuum, but they have some very serious problems that need to be fixed.-Eric Seidman, Baseball Prospectus

Key stat: .241

Players with Young’s frame and skill set tend to be very solid contributors that perform at relatively high levels. This year, however, Young fell completely off the map. Projected to generate a .276 EqA, Young was sent back down to the minors August 9 with a triple-slash line of .194/.297/.359, which might not ring alarm bells if compiled in a smaller sample at the beginning of the season. It does, however, really become puzzling over 366 plate appearances, half of which came in a bandbox home park. Since returning Aug. 29, Young hit .253/.350/.494 in his first 101 plate appearances, which has raised his seasonal EqA to .241-still a full 35 points below the projected mark. Starting outfielders, even those with the greatest of gloves, need to muster an EqA above .241 to merit regular action.-Eric Seidman, Baseball Prospectus Rumor Central

Free agency: Even with a surgically repaired shoulder that injury expert Will Carroll has told us is no sure thing in terms of recovery, it’s hard to imagine Arizona declining the option on Webb. Getting only a half-season of Webb is better than allowing a ragged fan base to see him toss a million ground balls for the Mets or Dodgers. But even with Webb, GM Josh Byrnes will have about $15-20 million to spend, and the D’backs need another arm. They may think mid-level talent makes sense, so perhaps importing the likes of Joel Pineiro would work. And hey, there’s always Jon Garland.

Moves: With all due respect to the power of tattoos to draw a crowd, the fact that current second baseman Ryan Roberts has 30 of them doesn’t mean he’s the answer. Roberts is a natural third-bagger and a great utility guy. Expect the D’backs to look for a cheap middle infielder with some pop. Possible calls could go to Orlando Hudson for a return engagement, Ronnie Belliard, or even Placido Polanco.

Who 2 Watch 4: Brandon Allen, 1B

Arizona fans are already getting a feel for their first baseman of the future, as Allen has shown serious power with a ton of strikeouts so far in his big-league debut, but he’s a better pure hitter than this, as evidenced by his .298 batting average at three levels, including a .324/.413/.641 line for Triple-A Reno after the trade that acquired him from the White Sox for Tony Pena. Chicago is going to regret this one.-Kevin Goldstein, Baseball Prospectus

Draft recap

Signed: 36 of 54
Spent: Just over $7.5 million
Hit: Matt Davidson, 3B (35th overall): Davidson may have been the best prep power bat in the draft, and he ranked 15th overall on Keith Law’s Top 100. He signed for $900,000 and may very well prove to be worth twice that.
Miss: Matt Helm, 3B (216th overall): Arizona gave Helm $500,000 after he missed most of his prep season with knee and ankle injuries. It could pay off, as one area scout believes Helm was the top high school talent in the state of Arizona when the season began-and calls Helm a “good bet to be something.”-Jason A. Churchill,

The Bottom Line

The Diamondbacks have a bright future in spite of this year’s disaster. Dan Haren remains an ace. Max Scherzer put together a solid season and continued to display All-Star potential. Reynolds is on pace to hit 45 home runs. Justin Upton‘s statistical peers at 21 years of age produce a list that includes a number of Hall of Famers. Add in the emergence of Miguel Montero as a backstop, the decent performance of fill-in Roberts, and the raw talent of reliever Juan Gutierrez, and it becomes easy to see how the Diamondbacks could play above the .500 mark next year. A healthy and effective Webb could be the difference between contending and being fourth-place finishers. It might not happen next year, but they could certainly be in the mix come 2011 as their younger players develop on all fronts.-Eric Seidman, Baseball Prospectus

A version of this story originally appeared on ESPN Insider Insider.