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The 5 biggest regrets of the last MLB offseason

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If every team could pull a lever to undo a move from last offseason, which five teams would move the quickest?

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We were so innocent back then. Look at us, all excited about the White Sox and Padres, envious of their busy offseasons. Right when we thought the Padres were done, blammo, James Shields, and right after that, gadzooks, Craig Kimbrel. The White Sox dumped a bunch of money on a closer and Melky Cabrera, and it made sense at the time because ... well, I can't remember. But it was fun!

The dust has settled, and we have a better idea of which moves were a mistake and which moves were inspired. Also, the dust came from postseason hopes that burned up upon reentry. It smells like burning hair. Do not breathe the dust in. Please get away from the dust.

It's too late for these teams. Here are the five offseason moves that teams would undo if they could. If you gave them a lever to pull, they would pull it, possibly over and over again, while sobbing regretfully.

5. Marlins trading Nathan Eovaldi for Martin Prado

The Marlins are currently on pace to lose 97 games, which gives them a shot to lose 100. Even more than the Padres and White Sox, they're the face of "Wait, they thought they had a shot?" They were all in, dealing prospects for Dee Gordon (which made them look smart) and Mat Latos (which ... didn't), but at least they'll have Gordon for the next couple years, and at least they got some value back when they returned Latos to the transaction store, slightly dinged.

The Eovaldi move is going to haunt them, though. He's about to get expensive through arbitration, but he's still a young, cheap, and relatively inexpensive arm, something a team should trade if they're supremely confident in their rotation depth. Which brings me to a list of teams in baseball that should be supremely confident in their rotation depth:

  • ...

That isn't to say that teams should never trade from their stashes of pitching depth, but remember when the Dodgers supposedly had dozens of starters with nowhere to put them? They just traded for two more, and they're already starting to have buyer's remorse that they didn't shop at the expensive boutiques. The Rays looked like team with 10 starting pitchers before the 2014 season, and just over a year and a half later, they've dipped into the depth below the depth to build a successful rotation. They're lucky they didn't play fast and loose with their extra pitchers. A team that's trading a talented fifth starter because they have a sixth starter should really, really, really be sure they're getting the appropriate value back.

Prado's been okay for a couple years now. Not a player who's going to mess up the lineup. Not a player who's going to make his team worse. But just okay. He's already paid a fair sum, he's over 30, and he had a troubling gulf in his walk and strikeout totals last year, which was totally unlike him. The power he showed in Yankee Stadium was going to disappear in Marlins Park, and presumably even the Marlins expected it to.

It was a weird fit for a weird plan. Meanwhile, after a funky and erratic start, Eovaldi has some serious buzz in New York. Now he's occasionally throwing 102, which is absurd for a starter, and his splitter is revamped and deadly:

The Marlins could find someone like Prado on the free agent market this offseason. They won't be able to find a pitcher like Eovaldi, not for the low price he's going to command for the next two years.

4. Twins signing Ervin Santana

Goodness, what a weird move. The Twins had the best 1-2 prospect punch in baseball, but both Byron Buxton and Miguel Sano were delayed in 2014 because of injuries. When they signed Santana, it was an indication that they were going to sacrifice the long-term payroll to make sure they were going to contend in 2015, which, wait, what's the rush? Planning for happy surprises in 2015 and allocating their money for a major 2016 push made far more sense.

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Because they got those happy surprises. The Twins have used a little luck and a little talent to hang around the Wild Card race, with Sano arriving a touch ahead of schedule to become a major part of that. Except Santana isn't helping at all for the postseason push, and he can't help at all if they make the postseason because of his suspension for Stanozolol. The worst part is that he could futz up next year's chances, too, which always should have been the priority for the Twins.

Without Santana and Ricky Nolasco, the Twins could have arrived at the winter meetings with $100 million in unmarked bills, setting up a little stand in the lobby with glossy brochures of Sano and Buxton, letting free agent pitchers come to them. Instead, the plan is probably something like "hope Santana and Nolasco are good for the first time in two or three years and, uh, fill in the pieces around them?" For a team that's had a little trouble developing their own pitchers, spending on free agent arms was the right move. But why the last two years? Why those two pitchers?

Even if Santana didn't get suspended for PEDs, it would have been a questionably timed move. Add in the suspension, and it's a debacle for a team that could have used the financial flexibility at the trade deadline, if not this offseason.

3. Red Sox signing Hanley Ramirez

The Pablo Sandoval signing was a mess, don't get me wrong, but a lot of that has to do with the benefit of hindsight. He was still in his mid-20s, coming off a productive year and a stretch of four average-to-great years with the Giants. He looked like a great fit for Fenway, and he filled a position of need. The pieces are all still there, and I wouldn't be surprised to see the Red Sox give him another year -- maybe even two -- to make good on the deal. Maybe an offseason of reflection and quiet contemplation will do him wonders.

Note: You should not expect Sandoval to spend the offseason reflecting and quietly contemplating.

The Ramirez signing was a bold, dumb move, though. It was a thought experiment: In theory, if Manny Ramirez could play left field, couldn't everyone play left field?

Nope! Very nope. So very nope. Ramirez has been playing left field like he's wearing a backwards Batman cowl, and he forgot to hit along the way. It was the roster-shaping equivalent of "if I take off my clothes and jump into the pool, everyone's going to follow me and this party will turn around," a miscalculation that was obvious after about five seconds.

With Sandoval, the Red Sox can try again because it's not like they have a better choice at third, at least not yet. Ramirez makes so much money, and the Red Sox have a full outfield, a living legend at DH and an understandable desire not to assume Ramirez can handle first base just because anyone can do it. He's a positionless player on a team that doesn't have a need for him, and he makes too much to leave on a doorstep somewhere.

If it were anyone else, some sort of super-utility role would make sense, where Ramirez gets his starts based on the opposing pitcher, the various ouchies in the lineup, and other in-season concerns. As is, Ramirez might be the biggest start-or-pout candidate in the majors, even if there's no justification for him to keep starting. It's a mess, and if the Red Sox could pull the undo lever on just one of their many unfortunate moves this offseason, this would be the one.

2. Everything the Padres did

Maybe that's not fair to the players who are doing what they were expected to, like Justin Upton and (more or less) Derek Norris, but this isn't about the decision to go for it. It's about the Padres' theoretical desire to hit a reset button if they could. If they could do that, they would have:

  • A starting shortstop next year
  • At least one or two rotation-ready, cheap starters
  • Yasmani Grandal
  • Not Melvin Upton
  • About $148 million to spend on future contracts
  • Close to a dozen extra prospects
  • The No. 13 pick in the 2015 draft

Pretend that's all on the table. And the Padres can get it back. All they have to do is give up James Shields, Matt Kemp, Derek Norris, Melvin Upton, Craig Kimbrel, the ability to negotiate with Justin Upton exclusively for a week, the compensation pick if/when Upton leaves, and Wil Myers. Do they do it? It would be tough to give up on Norris and Myers, but everything else seems like something they could pick up this offseason with those extra millions, keeping the prospects along the way.

The idea to go for it was inspired, and the fans were truly excited for a spell. If they could undo it all, though, and get back exactly what they gave up, though, I don't think they would spend more than five seconds thinking it over.

1. Rays trading for Steven Souza instead of Trea Turner and Joe Ross

It was a major surprise that the Rays were willing to trade Wil Myers, but it makes sense in retrospect. He was, and remains, a confusing, confounding player with all the talent in the world, but no guarantees that he'll ever realize it. He was a defensive enigma. Trading him a year too early made more sense than trading him a year too late, considering how much of his trade value was wrapped up in unrealized potential.

So the Rays shopped him around. And the Padres said, yes, we will give up two exciting prospects for him -- a pair of first-round picks with six or seven years of team control left. The Rays entertained the offer, but then essentially moved those players for a 26-year-old outfielder whose perceived value was based on about 90 games of Triple-A success.

Again, you could see what the Rays were thinking at the time. They wanted to eat cake, and they wanted to stuff the freezer with more cake. They were reloading, not rebuilding, and Souza was supposed to come close to what Myers could do in the present, Burch Smith added to the rotation depth in the majors, and Jake Bauers and Travis Ott helped the lower levels of the minors. It was a near-win for the present, combined with a win for the future. Bauers, Ott, and the injured Smith are all still prospects, so don't sell that part of the deal short. In five years, we might look at dumb articles like this in a whole new light.

But they would almost certainly take Turner and Ross with the benefit of hindsight. Turner is already up, and he's going to start for the Nationals next year. Ross is already in the Nationals' rotation, and he looks like a future ace. There is an All-Star ceiling for those two that might be realized for 2016. Souza has been a disappointment, a player with a limited ceiling who doesn't have the same chances to overcome Tropicana Field that Myers did.

How in the heck did the Nationals worm their way into that deal in the first place? They didn't have a place for Souza, so it made sense that they were talking with the Rays, but how did they come away with the two best prospects in a deal that featured Wil Myers? A lot of teams have questions about last offseason. Nothing comes close to the aww-shoot the Rays are feeling about this one.

OK, maybe the Padres come close. Also, the aw-shoot of 29 different teams when it comes to Jung-Ho Kang is pretty strong, too. When it comes to the fortunes of a super-low budget team with designs on contending in 2016, though, it sure would have been nice to have a starting shortstop and No. 3 pitcher making the major league minimum. Sure would have been nice.

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