The Best Transactions of the 2016 Offseason

While the offseason isn’t quite over yet, we’ve reached a point at which most of the major transactions have probably already been made. Sure, we might see Jonathan Lucroy moved in a deal over the next few weeks, but outside of some unforeseen blockbuster, it’s mostly going to be minor moves from here on out. So, with the heavy lifting behind us, it’s time to take a look back at the 10 moves that I most liked this winter.

Overall, I’ve tried to balance the value added by acquiring a player — not just his own performance, but his impact on the team’s chances of reaching and advancing in the postseason — with the price paid to make the move. In some cases, teams on this list made themselves worse in the short-term, but the potential long-term benefit suggests that it was a worthwhile sacrifice. Other teams are here for making shrewd additions that improved their chances in 2016, and one of these moves even manages to potentially improve the franchise in both the present and future; you’ll find that rare big win at the very top the list.

Of course, these are all just based on my perceptions at this point in time, and several of these moves won’t look so hot as time goes on. Last year, I really liked the Chase Headley deal for the Yankees and put the Red Sox’ acquisition of Wade Miley one spot ahead of the Blue Jays’ pickup of Josh Donaldson, so, you know, don’t take this as gospel. But based on how I look at these moves right now, without the benefit of hindsight, there are the 10 moves I’ve liked the most this offseason.

Honorable Mentions

Rays Acquire Brad Miller, Danny Farquhar, and Logan Morrison
Rays Acquire Corey Dickerson and Kevin Padlo
Yankees Acquire Aaron Hicks
Cubs Acquire Adam Warren
Mets Acquire Neil Walker
Dodgers Sign Howie Kendrick
Mariners Sign Hisashi Iwakuma
Cubs Sign John Lackey
Giants Sign Denard Span

#10: Phillies Turn Reliever Into Assets
Acquire: Vincent Velasquez, Mark Appel, Brett Oberholtzer, Thomas Eshelman, Harold Arauz
Cost: Ken Giles, Jonathan Arauz

Let’s make no mistake about it: Ken Giles is an excellent reliever, and with five years of team control remaining, the Phillies gave up a valuable piece in this trade. However, rebuilding teams don’t have much need for elite relief pitchers, and turning one guy with an expiring shelf-life into a bundle of interesting pitchers is exactly the kind of move the Phillies needed to make this winter. Velasquez’s health and Appel’s ability to get high-level hitters out are both still in question, but there’s more than enough upside here to make this a terrific deal for the Phillies.

#9: Cubs Add Excellent Veteran Depth
Acquire: Ben Zobrist
Cost: 4 years, $56 million

With Addison Russell, Starlin Castro, and Javier Baez around, the Cubs already had a crowded middle infield, and could have simply gone forward with the kids. With perhaps the best roster in baseball heading into 2016, however, they saw an opportunity to upgrade at a good price and took advantage. Adding Zobrist as their everyday second baseman not only makes them better at the position than they would have been with either Castro or Baez, but it allowed the team to ship Castro to New York for Adam Warren, who bolsters the pitching depth. For the extra $4 million per year they took on with Zobrist as opposed to keeping Castro, they significantly improved their lineup and their bullpen; it’s hard to make that kind of upgrade for such a modest cost these days.

#8: Brewers Smartly Rebuild
Acquire: Chase Anderson, Isan Diaz, Aaron Hill
Cost: Jean Segura, Tyler Wagner

This is the kind of small move that isn’t going to draw a lot of attention in offseason recaps, but it exemplifies the fantastic rebuilding plan that Milwaukee has executed this winter. Rather than keeping Segura around for any longer, letting even more of his distant prospect-sheen wear off, the Brewers managed to turn the last vestige of his 2013 All-Star reputation into a starting pitcher who is potentially more valuable both now and in the future, along with a young infield prospect whose early statistical indicators suggest he could turn into a player of legitimate value. The Brewers had to take on a portion of Hill’s contract in order to facilitate the swap, so they didn’t quite turn a bad shortstop into a better pitcher and a nice prospect, but for the small cost of throwing away some money in a rebuilding year, this was still a fantastic acquisition for Milwaukee.

#7: Angels Upgrade at Shortstop
Acquire: Andrelton Simmons, Jose Briceno
Cost: Sean Newcomb, Erick Aybar, Chris Ellis

This summer, I ranked Andrelton Simmons as the 30th most valuable trade chips in all of MLB; a few months later, he was traded for a high-risk pitching prospect and an average player in the final year of his contract. Certainly, teams don’t pay for defensive excellence like they do for offense, but no one questions Simmons’ value in the field, and despite the truth that defense peaks early, previous defenders at this level have proven to be quite valuable even as they age. This is the kind of return that you’d expect for a short-term upgrade, but Simmons is signed through 2020 at below-market rates, giving the Angels some real value even beyond 2016. The fact that no one else stepped up to outbid the Angels suggests that the league doesn’t place as high a value on Simmons as the public does, or maybe the industry thinks we’re selling Sean Newcomb short, but from my perspective, the Angels added one of the best shortstops in baseball for a pitcher with a high likelihood of failure.

#6: Cubs Add Another Young Star
Acquire: Jason Heyward
Cost: 8 years, $184 million; opt-outs after third and fourth years

With a core group of young stars that carried the team to 97 wins a year ago, the Cubs didn’t need the best free-agent position player on the market, but they had the resources to poach him from their division rivals, and in doing so, they swung the balance of power in the NL Central for years to come. While signing Heyward to play center field adds an element of risk to the deal, his overall value should make him a high-quality contributor even as he adjusts to a new position, and the Cubs are buying enough prime-years that Heyward’s elite defensive value shouldn’t be expected to dissipate too quickly. The dual opt-outs limit the upside here, making it almost impossible for the Cubs to get a long-term bargain, but the price for an elite talent was right, and the Cubs are in perfect position to take advantage of Heyward’s short-term value.

#5: Mets Bring Back Yo
Acquire: Yoenis Cespedes
Cost: 3 years, $75 million; opt-out after first year

All winter, the Mets told anyone who would listen they weren’t re-signing Yoenis Cespedes. They even signed Alejandro De Aza to serve as outfield depth, signifying that they were moving on, but as his price began to drop, the Mets found themselves in a position where they simply couldn’t ignore the benefit any longer. Cespedes isn’t a great fit as a center fielder, and Juan Lagares probably would have been just fine out there if given the opportunity, but you don’t get too many chances to sign an above-average player with this kind of limited risk. Clearly, the market didn’t love betting on Cespedes’ future value as he aged, but with just a three year commitment — and the dangled carrot of the opt-out as motivation — it’s hard to see this deal going too terribly wrong. And if Cespedes continues to hit for power the way he did last year, this could end up being the free-agent steal of the winter. For a team with elite pitching and a chance to get back to the World Series, $75 million to bring Cespedes back to New York was just too good of a deal to walk away from.

#4: Padres Get a Haul For Their Closer
Acquire: Manuel Margot, Javier Guerra, Carlos Asuaje, Logan Allen
Cost: Craig Kimbrel

I’ve been pretty down on a lot of the moves A.J. Preller has made since taking over in San Diego, but the second of his Craig Kimbrel trades could very well turn out to be a massive win for the franchise. While Kimbrel remains one of the game’s best relievers, he’s not all that young or cheap anymore, and yet the Padres still managed to turn some high-risk years of a guy they didn’t need into a massive talent return. In Margot and Guerra, the organization landed two top-100 prospects, and Allen is interesting in his own right; this is the kind of return that the Padres could have only dreamed about when they realized they’d have to ship out some of their veterans. While minor leaguers are always high-risk propositions, getting this kind of talent back for a declining reliever makes this a big win for the Padres.

#3: Royals Retain Their Best Player
Acquire: Alex Gordon
Cost: 4 years, $72 million

While Lorenzo Cain may be more obviously exciting, and Salvador Perez gets more headlines as the team’s leader on the field, Alex Gordon is the Royals’ best player, and one of the primary reasons they’ve been able to turn their franchise around in recent years. Despite his advancing age, Gordon has sustained his across-the-board skills, and while he won’t be a gold glove left fielder forever, he’s good enough to justify this contract in the next couple of years, even if he’s not that good by the time it expires. Gordon is easy to take for granted, but he may very well have been the second best available free-agent position player, and the Royals managed to bring him back to Kansas City for the kind of price that gets you a back-end starter these days. I have been a pretty vocal critic of a lot of the moves the Royals have made the last few years, but re-signing Gordon was one of the best decisions anyone made this winter.

#2: White Sox Find a Third Baseman
Acquire: Todd Frazier
Cost: Frankie Montas, Trayce Thompson, Micah Johnson

A year ago, the White Sox tried to go for it despite a flawed roster, and ended up struggling due to the vast amount of at-bats wasted on replacement-level scrubs. This winter, the White Sox have again attempted to push their chips to contend in the short-term, but those hopes got a nice boost when they somehow managed to convince the Reds to give them Todd Frazier for a package of talent that won’t cripple the organization. Frazier’s second-half swoon may have dragged his value down below a reasonable level, since teams saw him hit just .220/.274/.390 in the second half, but kudos to Rick Hahn for taking advantage and turning some spare parts into a +3 to +4 win third baseman. With Frazier at third base, the team has turned a black hole into a real strength, and while they could still use some additional improvements, the Frazier acquisition should go a long way to getting the White Sox back into the AL Central race.

#1: Braves Reload and Improve Simultaneously
Acquire: Ender Inciarte, Dansby Swanson, Aaron Blair
Cost: Shelby Miller

It’s still actually hard to believe the Braves pulled this off. Shelby Miller is a solid pitcher, having been worth between +2 to +3 WAR per season depending on how much weight you put on FIP or ERA. With his three arbitration years remaining, Miller represents a nice value for a mid-rotation starter, and is still young enough that it’s not crazy to think he might have some room for improvement. But in a market flooded with free-agent pitching, and plenty of other teams looking to sell their starting pitchers as well, the Braves still somehow managed to flip three years of Miller for five years of Ender Inciarte — arguably a player of nearly equal value on the field, and one who has five years of control remaining himself — as well as the #1 pick in last summer’s draft, plus they got one of the Diamondbacks better pitching prospects just for the heck of it.

Inciarte and Blair for Miller would have been something like a fair swap on its own. Or, separately, maybe the Braves requesting Swanson straight-up for three years of Miller could have been justified as a reasonable asking price, given the risky nature of prospects. But to somehow land all three players in the deal? It’s still remarkable, even a couple of months later. Inciarte probably offsets almost all of the lost value the team gives up in 2016 by not having Miller on the mound, and it’s not unreasonable to think Blair could be pitching in Atlanta this summer, so it’s possible that the Braves actually improved their 2016 record by making this deal. Except they get two additional years of control on the big leaguer they acquired, plus whatever Blair turns into, and a top-20 prospect who could be their franchise shortstop beginning in 2017.

We don’t see too many trades like this anymore. This is the kind of move that has a chance to be the modern-day version of Bartolo Colon for Grady Sizemore, Cliff Lee, and Brandon Phillips. It probably won’t turn out that way for the Braves, but the fact that they were able to make a move that has that kind of upside made this an easy pick for the best move any franchise made this winter.