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The Padres won the offseason 16 months ago, then everything fell apart

James Shields is gone, which means it's time to rank the sad transactions from the Padres' sad 2014-2015 offseason.

Jake Roth-USA TODAY Sports

With the benefit of hindsight, I'm starting to think that the Padres' decision to go all-in before the 2015 season was a bad idea.

Wait, hear me out. There is supporting evidence, and the James Shields trade just reinforces the regret and pain. He was supposed to be the final piece, the top starter they needed to help a lineup that was almost entirely turned over. He was ineffective, homer-prone, and expensive, instead.

This was a headline before they signed Shields:

The wild offseason of the amazing Padres

Even if I had reservations about most of the players they acquired, it's not like they were all going to flop. Then they signed Shields, and they were officially the lords of the offseason. A month later they traded for Craig Kimbrel, and they were the intergalactic lords of the offseason.

A year-and-a-half later, the Padres were willing to give Shields away for a couple of raffle tickets and salary relief. It ended up being a disastrous deal. Almost all of the transactions were disastrous, really.

That means it's time to rank the Padres' trades and signings from the 2014-2015 offseason in order of pain. We'll cull through the Baseball-Reference transactions page, start with the least disastrous, and get progressively sadder.

7. Traded Jordan Paroubeck, Cameron Maybin, Carlos Quentin, Matt Wisler and 2015 competitive balance pick (round A) to the Atlanta Braves. Received Craig Kimbrel and Melvin Upton Jr

Matt Wisler would sure look good in the middle of a Padres rebuilding program, but they still made out well with this deal, just in a roundabout way. They traded Kimbrel to the Red Sox and recouped their biggest losses, with three of the prospects (Logan Allen, Carlos Asuaje, and Manuel Margot) performing well in the minors right now, and Javier Guerra's glove still works even if his bat doesn't. I'm not prospect-savvy enough to know if I would prefer to have those three instead of Wisler, but it sure looks like it from here.

This was not a regrettable move from the Padres' regrettable offseason.

6. Traded R.J. Alvarez and Jesse Hahn to the Oakland Athletics. Received Seth Streich, Derek Norris and cash

Norris was never supposed to be Johnny Bench, but there was promise with his combination of power bat and acceptable defense behind the plate. It wasn't just theoretical promise, either, as he realized it in each of the last two seasons.

His start to the season was ghastly, but he's picked it up over the last month, and he's still relatively cheap for the next couple years. Alvarez and Hahn haven't done much for the A's, so this one could still be considered a winning deal.

This was not a regrettable move from the Padres' regrettable offseason. Stop here if you want to stay happy.

5. Signed James Shields for 4 years, $75 million

Let's check in with Twitter on February 9, 2015, the day James Shields signed with the Padres:

Ah, the parallels are magnificent. Somehow the White Sox went from winning the offseason to losing the real season to winning the real season, and they came away with the cherry on top of the other winning offseason. I don't know what this means, but it probably means everything.

The Padres will have paid roughly $45 million for two wins above replacement, Erik Johnson, and a prospect they could have had for $800,000 last summer. That's not great. But don't think of the glass being $45 million empty. Think of it as $27 million full. They can use that money on lots of things. Like James Shields, if he opts out of his contract!

4. Traded Seth Smith to the Seattle Mariners. Received Brandon Maurer

A minor deal, but one that really stinks in retrospect. Smith was one of the only hitters of any worth for the 2014 Padres, as he had a 134 OPS+ and proved that Petco didn't mess with him as much as the typical hitter. He was traded for a middle reliever because the new-look Padres were just loaded now.

Since the deal: 620 plate appearances with the Mariners, with 18 homers, a .346 on-base percentage, and a 120 OPS+. That last stat would lead this year's Padres, but you knew that. Perhaps even more damaging is that Smith would probably fetch a fair prospect bounty this deadline, while Maurer isn't a bet to make it through the season on the active roster.

3. Traded Max Fried, Dustin Peterson, Jace Peterson and Mallex Smith to the Atlanta Braves. Received Aaron Northcraft and Justin Upton.

The prize was supposed to be Fried, and he still could be, but he hasn't bounced back from his Tommy John surgery as quickly as the Braves might have hoped. Even without Fried's contributions, though, Mallex Smith is looking like someone the Padres should have hung onto. A plus defender with speed and doubles power will always fit nicely in Petco.

The real problem, though, was the Padres hanging on to Upton during the trade deadline last year. They didn't want to go full Marlins and sell the players that had just recently excited the fans, and that's understandable. But this would have looked a lot better if the Padres could have aped the Kimbrel deal, recouping their losses and and kicking the prospect can a little farther down the street.

2. Traded Jake Bauers, Rene Rivera, Burch Smith to the Tampa Bay Rays. Traded Joe Ross, and Trea Turner to the Washington Nationals. Received Jose Castillo, Gerardo Reyes, Ryan Hanigan and Wil Myers

Wil Myers is having a nice season. He's slugging .480, which is no small feat in San Diego. Even though it doesn't seem like he'll ever be a .300 hitter or big OBP guy, he's still just 25 and inexpensive.

Myers is a first baseman, though. It's possible that he could be a below-average corner outfielder again or an awful center fielder again, but he's probably found a home at first. That's going to limit his value, especially if he doesn't develop 30-homer power or better plate discipline. And to get that kinda-cool first baseman, the Padres gave up Joe Ross, who is probably an All-Star right now, and Trea Turner, who has a chance to be an All-Star for years at a much more important position.

The all-time WAR leader at shortstop for the Padres is still Ozzie Smith, who played just four seasons with them. They've employed 37 other shortstops since 1969, and they've combined for 24 WAR. I imagine that when Turner was drafted by the Padres, he was a little scared.

There's something more powerful than the Padres' ability to grind shortstop prospects into shortstop powder, though. And that's their legendary ability to regret trades. Here's another one, even if Myers is still a nice player to have.

1. Traded Zach Eflin, Yasmani Grandal and Joe Wieland to the Los Angeles Dodgers. Received Tim Federowicz, Matt Kemp and cash.

Here's the worst of the lot, the biggest mess of them all. The Padres gave a young starting catcher to their division and regional rival, and they received an expensive handyman's special in return. Kemp is hitting .236/.245/.464 for them this season, and his fielding is still the .245 OBP of fielding. He has four walks and 55 strikeouts, which gives you an idea of just how much he needs to cheat if he wants to hit a ball hard. He's under contract for three more years after this, with the Padres paying $18.25 million in every one of them.

It's the kind of deal that will hurt the Padres if they contend in the next three years because they'll be financially limited. It's the kind of deal that makes fans irritable and disgusted right now because they have to watch Kemp struggle. It's the kind of deal that can get even worse, with Eflin thriving in Triple-A for the Phillies (where he went in the Jimmy Rollins trade).

In a sense, this was the perfect metaphor for the entire offseason. The Padres got a guy who, if he worked out, had an MVP-caliber bat. Things didn't work out, and now it seems ludicrous that anyone ever thought they would. The optimism was misguided, and now there are regrets. Feels like I've heard that before.

Oh, right, it's their slogan for this season. Points for the honesty.

Seven moves of different scope. A couple of players worth keeping. A whole lot of regrets around them, though. The Padres were exciting as all heck just 16 months ago. Now they've ditched their final veteran puzzle piece, and they have to start all over. The dreams of the most exciting offseason of the decade are dead, and there's nothing growing out of the soil yet. What a cruel sport this can be.