2014 SB Nation MLB Awards: Rockies Most Regrettable Moment nominations

Last week, we presented the Rockies' nominees for the first 2014 SB Nation MLB Awards category, Funniest Moment. The line between that and today's list, Most Regrettable Moments, can be very thin, especially for a team that finished with the second-worst record in the National League. With that in mind -- and with the help of the readers -- I tried to keep this to things that weren't necessarily funny when they happened (though they can probably be laughed about right now).

Here are the nominees, in chronological order:

1) May 28: Howard sends Rockies into tailspin

Ryan Howard days as a good Major League Baseball player are behind him. The 34-year-old first baseman owns a .233/.309/.412 line since the beginning of the 2012 season, a far cry from his first seven years in the big leagues, when he averaged 41 home runs and a 139 OPS+ for a bunch of good Phillies teams.

But for one at-bat in late May, Howard was good enough to provide the turning point in an awful season for the Rockies. Howard hit a game-winning three-run home run off of Boone Logan, who was brought in specifically for the left-on-left matchup. That game was only the beginning of the troubles Logan saw in 2014; the veteran southpaw was an expensive disaster, and there was no better example of that than this. And the Rockies, who had a chance to regain some momentum with a series victory on a tough road trip, lost 10 of their next 11 games.

2) June 21: Brewers clear bases on wild pitch

The Rockies got their revenge a week later on a Little League home run by Wilin Rosario, but this might have been the event that caused a large chunk of the fan base to officially give up on the 2014 season. Friedrich, making his first big league start since 2012, didn't get any help from his defense while falling behind big early in this game. But he also didn't do himself any favors on this play:

Purple Row reader sevopie said it best in the comments:

That was the day I (mostly) stopped watching this season; I was pretty much embarrassed for the team after that one. I kept seeing things around the web for a couple weeks along the lines of "Hilarious Rockies fielding debacle" or "Worst defensive play ever," so I don't imagine many will forget that one for a while.

3) July 10: Monfort can't put down his iPad

Dick Monfort did not have a good July. First, there was his infamous "If product and experience that bad don't come!" message to a Rockies fan who traveled to Coors Field from Grand Junction only to see his favorite team get squashed. Later, Colorado's owner expressed his disdain for bringing an outside presence into the organization for fear that it might upset its culture.

But the worst of the worst was when, in another one of his iPad email rants, Monfort told a fan that "Denver doesn't deserve a team." More than 30,000 people showed up to Coors Field on a nightly basis to see a 96-loss team, but Monfort acted like his club's struggles were the fault of paying customers. The backlash was huge; players eventually became disgruntled, largely due to all of the negative attention surrounding the team's front office, and longtime general manager Dan O'Dowd stepped down after 15 years in the position.

Maybe things will be better with Jeff Bridich at the helm, but Monfort's gaffes left a significant part of the fanbase with little to no hope for real improvement at 20th and Blake, regardless of who works under the meat-packing millionaire.

@PurpleRow @psaundersdp Gracious yes, but it sounded pretty status quo to me. Might need to watch his emails though. pic.twitter.com/rDSQ4G5P6M

— Steve Baxley (@Steve__Baxley) July 9, 2014

4) July 31: Rockies stay quiet at trade deadline

July 31 was far too much like most other days of the season for the Rockies. They lost to the Cubs, 3-1, to clinch yet another road series loss in a game started by a pitcher -- in this case, Pedro Hernandez -- who should've been nowhere near the rotation. The problem is, it shouldn't have been that way; the Rockies had pieces to part with but chose to stand pat, leaving a bad taste in the mouths of fans all over the Rocky Mountain region.

Colorado received a good offer for Jorge De La Rosa and perhaps could have moved Drew Stubbs, Justin Morneau, LaTroy Hawkins and others to contending teams while hoping for an overpay. Instead, the Rockies continued to lose, had neither of their star players see the field again and, perhaps most importantly, missed a shot at improving their future.

Next up: Rockies Defensive Play of the Year. After you vote on the Most Regrettable Moment, leave your nomination for best glove work in the comments.