It was the type of game for which a team hungers for a proven, big game pitcher on the mound. Instead, the Sox featured a rookie with just three starts in the big leagues.

The start of a four-game series against the Rays represented a contest of such magnitude that Red Sox manager Terry Francona acknowledged that David Ortiz and Adrian Gonzalez likely would have been resting under other circumstances. A Sox team that was set to cruise into the playoffs just two weeks ago is now flailing while trying to hold on to a wild card spot, and Boston needed its top players on the field.

That made the identity of the Sox’ starter in some ways startling. For the tone-setting contest, the Sox would turn to Kyle Weiland, a pitcher who entered the day with all of 16 innings of big league experience.

That’s no knock on Weiland, who allowed four runs in 3 1/3 innings in Boston’s 9-2 loss, which trimmed the Sox’ lead to three contests. The Sox still regard the 25-year-old highly, and his performance in the minors this year suggests a pitcher who could emerge as an important member of the Boston pitching staff in 2012 or 2013.

Still, the fact that the Sox sent a pitcher with a 6.75 major league ERA, someone who entered the day having walked more batters (8) than he’d struck out (5), served as a dramatic commentary on the state of Red Sox pitching this September.

The pitching staff has quickly come apart at the seams, bringing the season to a state of crisis.

Josh Beckett? Injured. Erik Bedard? Injured. Healthy starters? Struggling. The bullpen? Unraveling, with Daniel Bard joining Matt Albers, Dan Wheeler and a revolving door of September call-ups as pitchers who seemingly can’t enter a game without giving up runs.

The net result has been a horror show for the Sox. In 14 games in September, the Sox feature a 6.55 ERA and 3-11 record, marks that made what appeared to be an unimpeded march into the postseason a suddenly uncertain proposition.

At this point, even if the Sox get to the postseason, plenty of skepticism has been engendered about whether this pitching staff is capable of doing anything to help propel the Sox through a short series against an elite offense.

All of that being the case, amidst what has been a two-week collapse by the pitching staff, two questions loom:

Could the Sox have seen this coming?

Could this fiasco have been avoided?

Those questions, in turn, point to the evaluations made by the club in the two previous months, particularly prior to the July 31 deadline for trades that did not require waivers, and to a lesser degree leading up to the Aug. 31 deadline for trades of players who were exposed to waivers.

Hindsight, of course, is in many ways an unfair vantage point from which to judge past decisions. Nonetheless, looking back over those evaluations is a necessary activity of front offices to determine how well their decision-making processes are working. 

Here, then, is a look back at how the Sox saw their pitching staff entering the July and August deadlines and the opportunities that might have existed for the club to avoid this startling September slump.

STARTING OVER IN THE ROTATION

THE DIAGNOSIS

As the trade deadline approached, the Sox recognized that they had serious concerns with their rotation. The starters were anchored by a pair of pitchers worthy of the title of "ace," as both Josh Beckett (9-4, 2.17 ERA through July 31) and Jon Lester (11-4, 3.17) had been dominant.

Those two, in turn, gave the team reason for optimism about its ability to compete on any given night. But behind them, the team recognized that its options were thinning quickly.

Clay Buchholz (6-3, 3.48) had been terrific when healthy, but the Sox had become aware that he was dealing with a stress fracture in his lower back that was likely to have him out for most if not all of the year. John Lackey (9-8, 6.20) had assembled a few good outings just before the deadline, but he nonetheless had spent much of the year being bludgeoned.

Daisuke Matsuzaka (3-3, 5.30) was done for the year after undergoing Tommy John surgery. Tim Wakefield (6-4, 5.06) had been so-so as a fill-in. Andrew Miller (4-1, 5.36) had been unpredictable. Weiland (0-1, 8.10) was a rookie with one good start and one bad one to his name in the majors.

The team had more depth -- in the minors, options included Weiland, left-hander Felix Doubront and veteran Kevin Millwood, while in the majors the team toyed with the idea of having standout swingman Alfredo Aceves start -- but certainly no one who offered a foundation of certainty.

In an ideal scenario, the Sox thought, they would like to add two starters whose major league track record and stuff suggested clear upgrades over the in-house options.

THE ONES WHO COULDN’T BE DONE

The Sox were active in exploring the market for a number of starters. Yet for the most part, there was no match to be had.

The team seemed to have the parts to match up with the Dodgers on a deal for right-hander Hiroki Kuroda, who was 6-13 but with a 3.11 ERA at the deadline, and who is 5-3 with a 3.60 mark since. But Kuroda, who had a no-trade clause, said that he would refuse any deal out of Los Angeles, thus forcing the Sox to turn their attention elsewhere.

The team discussed Ubaldo Jimenez (6-9, 4.46 entering the trade deadline with Colorado; 3-2, 4.98 in eight starts for Cleveland) with the Rockies, but the Sox did not have the elite upper-level pitching prospects to match the Indians’ package headlined by Drew Pomeranz and Alex White.

THE ONE WHO WAS NEVER ACTIVELY PURSUED

A compelling case can be made that no player who was dealt at the deadline has had the impact on the pennant race of Doug Fister.

The 6-foot-8 giant pitched far better than his 3-12 record with the Mariners would suggest. He had a 3.33 ERA over 21 starts in Seattle.

“He was outrageously good in Seattle,” noted Bedard. “All he needed was run support. He had the lowest run support in the majors. You’d feel bad for him, because he’d pitch his heart out and never get a win.”

Even so, Bedard’s claim notwithstanding, many viewed Fister’s ERA as a smoke-and-mirrors production. He was striking out just 5.5 per nine innings, and he naturally benefited from pitching in one of the most forgiving parks in the majors in front of one of the best defenses in the majors. His numbers were expected to take a hit if he was dealt elsewhere.

Yet, the opposite has occurred. In eight starts since being dealt (along with former Red Sox pitcher David Pauley) from Seattle to Detroit, the right-hander is 5-1 with a 2.28 ERA, 41 strikeouts, five walks and 7.2 punchouts per nine innings.

The Sox never foresaw such a performance. Indeed, when they made cursory inquiries on Fister, it became clear that they would struggle to match up with the Mariners.

After all, the Sox had to involve a third team in order to get the prospects to match up in a Bedard deal. And with Seattle aiming high on Fister, seeking a right-handed power bat (Detroit had Casper Wells to offer) in order to part with a player who will not be arbitration eligible until after the 2012 season and who will not be a free agent until after 2015, there were no real grounds for a deal.

Perhaps the Sox could have made a play for Fister if they’d offered a package centered around catcher/DH Ryan Lavarnway. However, the Sox had already decided that they would not deal Lavarnway for any of the players being offered by the Mariners.

In retrospect, at least right now, only two teams appear to have given Fister his due credit: the Tigers and Mariners. Seattle held out for a rich prospect package, and Detroit ultimately had enough conviction about Fister’s abilities that it was willing to part with a significant group of young talents (Wells, pitchers Charlie Furbush and Chance Ruffin, Double-A third baseman Francisco Martinez) to get him. 

If Fister continues his performance both for the rest of 2011 and beyond, then the Sox will be left to wonder why they didn’t evaluate Fister accurately. At the same time, they will not be the only team engaged in such an exercise.

THE ONE WHO WAS NEARLY ACQUIRED

The Sox wanted to acquire both Rich Harden and Erik Bedard, pitchers with swing-and-miss arsenals who were admittedly health risks but who could resemble top-of-the-rotation options if at their best. Acquiring both pitchers, moreover, would also give the Sox some insurance should injuries render either one unavailable.

In retrospect, Harden is the deal (or rather non-deal) that is the easiest to second guess. The Sox had a match with another team, and indeed, they’d even identified the players who would be involved in the deal. But the Sox chose not to make the move for the 29-year-old.

An agreement in principle had been struck, pending a review of the medical records, on July 30. Certainly, the Sox were aware of Harden’s injury-checkered history, but when they actually saw the documentation of his records, that was when they became convinced that the cost of acquiring him was too great to tolerate given the significant risk that he would make no more than a limited number -- perhaps a handful -- of starts on a five-day routine.

At that point, the Sox were no longer willing to make the deal as it had been constructed for first baseman Lars Anderson and a player to be named.

Anderson, once the top prospect in the Sox’ system, had seen his stock fall in the eyes of major league evaluators because he had yet to show big power numbers in the minors. Moreover, he had become blocked in the Sox organization by the acquisition of Adrian Gonzalez in the winter. In some respects, it was more difficult for the Sox to part with the secondary component of the deal.

The player to be named would be a prospect of some significance, a player in the lower levels of the minors who was far from the big leagues (hence with a wildly uncertain future) but with a significant ceiling. As such, the list from which the A’s would choose a player featured minor leaguers who were held in high regard by both organizations.

Among the players on the list, according to major league sources, were 18-year-old Raul Alcantara (who signed out of the Dominican for $500,000 two years ago and dominated in the Rookie Level Gulf Coast League this year before struggling after an aggressive promotion took him to Lowell) and 23-year-old Brandon Workman, a 2010 second-rounder who signed for $800,000 and went 6-7 with a 3.71 ERA and 7.9 strikeouts per nine innings in Single-A Greenville this year.

The idea of parting with such prospects -- especially Alcantara, who was already showing mid-90s velocity this year -- for perhaps just a few starts by Harden was difficult to stomach.

Yet, Harden has now made eight starts since the trade deadline -- more than the Sox considered likely given what they saw in his medicals. His results have been mixed.

He’s gone 2-2 with a 5.08 ERA, and opponents have a line of .271/.345/.475/.820 against him. He’s averaged about 5½ innings per start and has made three quality starts among his eight outings. Those numbers aren’t terribly impressive, but he does have a tremendous 10.8 strikeouts per nine innings.

It does bear mentioning that Harden was given extra rest prior to his most recent start on Wednesday (eight days) in order to allow him time to get back to full strength. Moreover, he hasn’t been dominant.

But had the Sox pulled the trigger, there is a reasonable likelihood that Harden would have offered the Sox greater rotation depth than what they currently have. More to the point, the concerns that led the Sox to pull the rug out from under this trade have not come to fruition.

The Sox likely would be a better staff right now with Harden than they are without him. All the same, based on his performance with the A’s, it is unclear how much of an upgrade the tantalizing right-hander with power stuff would have been.

THE ONE WHO GOT DONE

The Sox had identified Bedard as a desirable trade candidate as early as spring training, when it appeared that his stuff was trending back toward the dominant performances he’d produced -- when healthy -- with the Orioles and Mariners a few years earlier.

His stuff and execution of stuff with the Mariners this year (en route to a 4-7 record but with a 3.45 ERA and nearly a strikeout an inning) both suggested that he represented a clear upgrade over what the Sox had.

And while the Sox understood that he had a checkered health record -- including a month spent on the disabled list for a left knee strain just before the trade deadline -- they felt that Bedard would be healthy enough down the stretch to be worth the cost of admission. The left-hander was viewed as a safer bet, from a medical standpoint, than Harden. 

Bedard (1-2 with a 3.66 ERA and 32 strikeouts in as many innings) has been the better pitcher when on the mound to date. But Harden, surprisingly enough, has been the healthier one.

That said, those two pitchers should not be viewed as an either/or, since the Sox were working to acquire both. They did not choose Bedard over Harden. They simply got Bedard done; had they not been anxious about Harden’s medicals, or had they been able to renegotiate a modified deal with Oakland, then they likely would have had both.

THE ONE WHO LEFT

The Sox thought that Kevin Millwood could provide depth. It is worth noting that the Sox didn’t just capriciously release the veteran; instead, he chose to opt out of his deal (just as he did when he left the Yankees’ minor league system earlier in the year) and leave the PawSox once Boston acquired Bedard.

The line to the Boston rotation had gotten a bit too long for Millwood’s tastes, as he didn’t foresee a combination of events along the lines of what happened to the Sox a month later. Meanwhile, Colorado -- a barely fringe contender that was nine games out in the NL West -- had an immediate vacancy in its rotation.

It wasn’t that the Sox didn’t think Millwood could still be a useful major league option. He had veteran guile and an ability to locate his 87-88 mph fastball and curveball to both sides of the plate.

It was simply that the team had other options with better stuff, a list that included not just rotation members Wakefield and Bedard but also the depth options such as Miller and Weiland and Doubront, a group with better raw stuff than Millwood. Ultimately, the veteran recognized that and moved on to the Rockies, for whom he is 3-2 with a 3.68 ERA in seven starts, spanning 44 innings. 

Right now, their staff in tatters, the Sox would love to have Millwood as a potential source of stability. But five weeks ago, when the right-hander opted out of his contract, it would have been difficult to make the case that he should wait in the Sox organization for several weeks rather than looking for a more immediate opportunity elsewhere.

HOW DO YOU SPELL RELIEF? IN THE TRADE MARKET, WITH GREAT DIFFICULTY

The rotation was the clear priority for the Sox. But at times in late July when it became unclear whether the team would reinforce its group of starters, it made sense to look into the relief market.

To that point in the year, the need was not glaring in the bullpen -- a far cry from what’s transpiring in September.

Jonathan Papelbon (3.50 ERA, 60 strikeouts, eight walks in 43 2/3 innings through July 31) and Daniel Bard (1.76, 49, 13 in 51 innings) represented a dominant back end of the bullpen. Matt Albers (2.09 ERA, 43 strikeouts, 18 walks in 43 innings) and Alfredo Aceves (3.19 ERA) had emerged as pleasant surprises. Dan Wheeler (4.54 season ERA, but a 1.78 mark since returning from the DL in early May) had also joined the ranks of the reliable.

Certainly, it would have been natural to wonder whether Albers might return to earth. Even though his stuff had been, by and large, overpowering, his career track record made it reasonable to wonder if his performance was sustainable, particularly given the year-to-year (and even month-to-month) volatility of relievers. But of course that sort of skepticism is a powerful argument against trading for relievers in the first place, especially in the middle of the season.

The Sox felt relatively comfortable with what they had, particularly given the depth of right-handed options (with players such as Michael Bowden and Scott Atchison in Pawtucket to handle right-handed hitters) in the organization. From the left side, there was greater uncertainty, but the team hoped that someone from the group of Doubront, Franklin Morales, Randy Williams, Hideki Okajima and others could fill the void.

The Sox saw few potential impact relievers on the market. For most of those who did represent potential upgrades, there wasn’t much of a match with the clubs who were making them available.

Mike Adams was the biggest name to move at the deadline, going from the Padres (for whom he had a 1.13 ERA, 49 strikeouts and just nine walks in 48 innings) to the Rangers in exchange for a pair of well-regarded minor league starters in Robbie Erlin and Joseph Wieland.

Adams is one of the most dominant right-handed relief men in the game, someone whom any team would like to acquire. And he would not be eligible for free agency until after the 2013 season, thus making him even more appealing as a trade option.

But the Sox didn’t have the kind of pitching depth in their system to match what the Rangers offered. The Padres weren’t thrilled with the prospect pool in the Boston system, and the two teams never found a real basis to get close to any deals at the deadline.

The Orioles were willing to move Koji Uehara, and they ended up trading the 36-year-old (1.72 ERA and a remarkable 62-8 strikeout-to-walk ratio with Baltimore) to the Rangers -- who used their considerable prospect depth to undertake an incredibly far-reaching midyear overhaul.

But Baltimore, like most teams, typically seeks greater return when consummating intradivision trades. Given that approach, conversations with the Sox never advanced as far as even exchanging names.

After all, whereas Texas acquired the right-hander with freakish control for first baseman Chris Davis and pitcher Tommy Hunter, a comparable package of Sox prospects -- for instance, Anderson and Doubront -- likely would not have moved Baltimore to send Uehara to another AL East team. (Since the deadline, Uehara has a 5.27 ERA, but an excellent 16-to-1 strikeout-to-walk ratio for Texas.)

That same approach by the Orioles also represented an impediment to the possibility of a deal for left-hander Mike Gonzalez in August. Gonzalez might have been attractive as a left-handed specialist -- he’d held southpaws to a .211 average and .575 OPS with the Orioles, and in his first two weeks in Texas lefties were 1-for-9 with a walk against him. But again, the Sox were unlikely to find the acquisition cost for Gonzalez reasonable.

One reliever did move who has pitched quite well for his new club. The A’s dealt hell-on-righties submariner Brad Ziegler to the Diamondbacks. Ziegler had a 2.39 ERA for the A’s at the time of the deal (which sent power hitting, defensively challenged first baseman Brandon Allen and lefty Jordan Norberto to Oakland); since the July 31 deal, Ziegler has a 1.56 ERA in 17 1/3 innings.

The Sox had kicked around the idea of Ziegler, but in July the Sox felt that they had plenty of strength among right-handed relievers and that it made little sense for them to commit a prospect (or prospects) to land a right-on-right specialist.

In hindsight, that determination is easy to second guess, but then, at a time when the Sox’ pitching staff as a whole is in a freefall, there is plenty that can be second guessed. And it is only natural to embrace an exercise in revisionist history, and think through the deals the Sox didn’t make and how that might have altered the course of September.

FINAL THOUGHT

The reality is that the Bedard trade, at least for August, did exactly what the Sox hoped it would. The Sox rotation stabilized and became deeper, with Boston enjoying a 3.97 ERA from its starters during the month.

September has been another matter, with Sox pitchers hammered by injuries and ineffectiveness, resulting in a shocking inability to deliver even five innings on most nights, and a bullpen that is buckling under the weight of its season-long workload.

Could the Sox have done more to build insurance in case they were stricken by a sudden succession of ills? Yes. But then, it would have taken a nearly impossible degree of prescience to forecast such a succession.

Therein lies one of the cruelties of a potentially epic collapse. It strikes with such suddenness that there is no opportunity to prepare for it until it is too late.