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Help us choose the most regrettable Red Sox moment of 2014

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It may not have been 2011 or 2012, but 2014 wasn't without moments the Red Sox would like to have back.

Joe Nicholson-USA TODAY Sports

On Monday we asked you to vote for the funniest moment of the 2014 Red Sox season. Today, the SB Nations Awards nominations roll on with an altogether different category: the most regrettable moment of 2014.

You'd think that it'd be easier to find regrettable moments than funny ones in such a disappointing season. And, in a year like 2011 or 2012, you'd certainly be right. When things go well and then fall so suddenly apart in the end as they did in 2011, there are so many different decisions both in-game and out that can be called potential turning points.  And when a bad season plays out in the Soap Opera fashion of 2012 with anonymous text messages, there's plenty to regret there.

2014, however, was different. 2014 was bad, but in entirely mundane fashion. The only decision the Red Sox could have made to save the season was to abandon ship altogether on their young players in January and assume quite a few injuries to boot. And without a $250 million payroll there's no way to build a team like that without it ending in disaster.

So instead we turn to the small things. What could have made this season more enjoyable, and where did the Red Sox lose value in the margins?


1. Signing A.J. Pierzynski

If you didn't see this one coming, you're either new here or haven't been paying much attention. While technically this occured in December 2013, it was certainly a part of the 2014 season. And an awful part at that.

The Red Sox had come into the offseason with Pierzynski barely on the radar. They weren't terribly gung-ho about bringing back their own starting catcher in Jarrod Saltalamacchia after his defensive issues had almost cost them dearly in the playoffs, but there was interest in what could be a diminished market for Brian McCann, and perhaps even more in Philadelphia's Carlos Ruiz.

The Yankees went all-in on McCann, however, and Ruben Amaro Jr. pulled a Ruben Amaro Jr. by first outbidding the Red Sox, and then himself in giving Ruiz a three-year deal. The Red Sox backed off, and took A.J. Pierzynski because, well, he was all that was left.

One can't help but wonder if they wouldn't have been better just giving it a miss entirely. Pierzynski was never going to be good given a history of offensive mediocrity and defensive ineptitude, but he could not even live up to those low expectations in 2014, putting up a truly terrible line of .254/.286/.348 in his time in Boston while looking like, well, A.J. Pierzynski behind the plate.

As mentioned earlier, Pierzynski was hardly the difference between a winning team and a losing team. He was more an easy symbolic representation of everything that the Red Sox had left behind in 2013 than anything else. But he contributed nothing to the team, cost the Red Sox a fair bit, and was hard to root for to boot. It may not have been a more successful season without him, but it probably would have been better.

2. The Jon Lester negotiations

Hindsight, as they say, is 20/20. And with the benefit of a full season of hindsight, the Red Sox have to be looking back at their spring negotiations with Jon Lester and wondering "what if".

At the time, Lester was looking for a contract in the neighborhood of five years and $100 million. The demands weren't that high, but there were two issues.

The first: 2012 and, with it, the middle months of 2013. Lester's march through the postseason had left him looking like one of the best pitchers in the majors, but the two years leading up to that point had actually seen more bad than good from the lefty, leaving the Red Sox understandably reluctant to go all-in on Lester without first seeing how he looked in 2014.

The second: the home-team discount. The story goes that Lester mentioned the possibility of a home-team discount, the Red Sox "lowballed" him, and Lester shut the negotiations down  One wonders, if that had never been brought up at all, if they might have gotten something done before 2014 started.

And, really, that's when they had to get it done, because the biggest complication of all was 2014 itself. If Jon Lester was just his usual strong self, the sort of pitcher the Red Sox saw from 2008 to 2011, then there's every possibility that he and the Red Sox would have come together on a deal before the chance to trade him even came about. Instead, Lester stepped up his game to a whole new level, emerging as a legitimate Cy Young candidate, splitting a 2.46 ERA over 220 innings between Boston and Oakland, walking a career-low 48 batters while approaching a career-high in strikeouts. With that sort of performance in a contract year, any chance the Red Sox had of keeping Lester out of free agency vanished.

We all know the rest of the story. Lester was traded to the Athletics, and now we're all left wondering if he's pitched his last game in a Red Sox uniform.

If we're taking away context, ignoring the historian's fallacy, and going full-on hindsight, this is the easy choice. And even with all that taken out, it's a strong contender.

3. Bringing back Stephen Drew

The beauty of the Stephen Drew move, at the time, was that it had no real downside. The money was money the Red Sox simply hadn't found a place for in the offseason that would essentially just vanish if left unspent. If Drew brought the Red Sox some much-needed life, excellent! If he didn't, they were none the worse for wear.

So how can this move be regrettable? It all comes down to your interpretation of Xander Bogaerts' season.

To some, Xander Bogaerts is just a sophomore who suffered a traditional, if pronounced Sophomore slump. To others, Xander Bogaerts is a shortstop who was forced into an unfamiliar position at third base by Drew, completely derailing what had been a fantastic season through the first two months.

The numbers line up, too. Xander finished his last game at shortstop in the first half with a .816 OPS. His next two games went well, but from that point to the trade deadline when Drew was shipped off to the Yankees for...well, for funsies...Bogaerts hit .182/.217/.300.

The argument against is that it took another month for things to get better. Bogaerts returned to Shortstop in August, but hit even worse in that month, only bouncing back with a .806 OPS in September.

Depending on your view of things, signing Drew was either an unsuccessful but ultimately low-cost attempt to revive a struggling Red Sox team, or an entirely successful if unintentional sabotaging of what was looking to be the introduction we had all hoped for from Xnader Bogaerts. We leave that up to your vote.

4. Holding onto Koji Uehara

Again, this one is up for some debate.

Heading into the trade deadline, the Red Sox were clearly out of contention, making the only question what return they would see for their assets. Jon Lester netted Yoenis Cespedes, John Lackey brought back Joe Kelly and Allen Craig, and Andrew Miller was good for Eduardo Rodriguez, who now ranks in as a top-5 prospect in Boston's system by most estimation.

And Koji Uehara? Koji stayed, and the Red Sox got nothing for the last few months of his season.

The good news is that Koji is also back, signed to a two-year deal during the exclusive negotiation period. And, if you think that Boston keeping him at the deadline is the reason he's going to be back in 2015 (and you like the fact that he'll be back in 2015), then this doesn't seem like a regrettable outcome at all.

If, however, you think the Red Sox could have had Koji back at that price even after a midseason trade, then that's one heck of a missed opportunity given that Andrew Miller was worth a fairly impressive prospect himself.

Once again, we leave it up to your vote.