Each MLB Team's Biggest Offseason Success of the Last 10 Years

As we continue to wait on the final few big pieces of MLB's 2023-24 free agency puzzle to find where they fit, let's look back at every franchise's best November-March decision from the past decade.

We combed through every team's offseason transaction log from the past 10-plus years, looking at free-agent signings, acquisitions via trade and long-term extensions* in search of what has been the biggest home run of a single winter move.

In some cases, there are a bunch of viable candidates. The Texas Rangers made great move after great move en route to becoming the 2023 World Series champions. While neither the Toronto Blue Jays nor the New York Yankees have made a World Series in over a decade, both have five strong options for this list.

For others, it was a challenge to even find a second move worth considering. Every team had at least one really successful transaction, though.

Teams are broken up by division and listed alphabetically within each one.

*For the extensions, only the years of team control added were considered. For instance, the Phillies signed Aaron Nola to a four-year extension (plus a club option for a fifth year) in February 2019, but he still had three years of arbitration eligibility remaining at that time. All they really gained was two years of team control, which can't even hold a candle to some of their free-agent acquisitions. In all but one case, that kept long-term extensions from making the cut.

Baltimore Orioles: Traded for RHP Kyle Bradish (Dec. 5, 2019)

The O's have made two excellent one-year acquisitions in the past decade, signing Nelson Cruz for what was maybe the best season of his career in 2014 and trading for Mark Trumbo in advance of a 47-homer campaign in 2016—though, they ruined that one a bit by re-signing him for three miserable years. But the best long-term move was trading away Dylan Bundy for (among others) Kyle Bradish, who emerged as a borderline ace this past season and should be a key cog of their rotation for the next five years.

Boston Red Sox: Signed OF/DH J.D. Martinez (Feb. 19, 2018)

J.D. Martinez is a fantastic reminder that an offseason signing could be better late than never. He waited until almost the start of spring training to sign that five-year, $110 million deal with the Red Sox. He was worth the wait and worth every penny, especially in the first year of the deal when he finished fourth in the AL MVP vote and played a huge role for a World Series champion.

Trading for Craig Kimbrel in Nov. 2015 was also a strong candidate here.

New York Yankees: Signed 2B/3B DJ LeMahieu (Jan. 11, 2019)

Trading for Didi Gregorius was great. Extending Brett Gardner was better. And signing Gerrit Cole has been awesome thus far. But it's hard to argue with the return on investment the Bronx Bombers got out of DJ LeMahieu. On a two-year, $24 million deal, he hit .336 with 162-game averages of 30 home runs and 107 RBI, finishing top-four in the AL MVP vote both years. He also put up similar numbers between those two postseasons, so it's not his fault the Yankees haven't been to a World Series since 2009.

Tampa Bay Rays: Traded for OF Randy Arozarena (Jan. 9, 2020)

Certainly an argument to be made that signing Brandon Lowe to a six-year, $24 million extension before the start of 2019 was Tampa Bay's savviest offseason move. Dumping Austin Meadows on Detroit in exchange for Isaac Paredes was also rather brilliant. But trading for Randy Arozarena takes the cake. His 10-homer run through the 2020 postseason was the stuff of legends, and his AL Rookie of the Year trophy the following year was one of the most predictable ever. With at least 20 home runs and 20 stolen bases in each of the past three seasons, he has been a gigantic part of their sustained success.

Toronto Blue Jays: Traded for 3B Josh Donaldson (Nov. 28, 2014)

Toronto had maybe the best one-year move of the past decade, signing Robbie Ray for $8 million and getting the 2021 AL Cy Young out of it. But trading for Josh Donaldson in advance of his first year of arbitration eligibility was even better. Donaldson immediately won AL MVP in 2015 on a $4.3M salary and finished fourth in that vote the following year, still at a team-friendly price of $11.65M. All told, he was worth 19.5 bWAR in his three-and-a-half years in Toronto.

Chicago White Sox: Traded for RHP Lucas Giolito, RHP Reynaldo López and RHP Dane Dunning (Dec. 7, 2016)

The White Sox have made a bunch of Atlanta Braves-ish brilliant extensions over the past decade of offseasons, locking up the likes of José Abreu, Tim Anderson, Eloy Jiménez, José Quintana and Luis Robert Jr. on long-term deals. But trading OF Adam Eaton to the Washington Nationals for the above trio of pitchers was a heist. Better yet, the White Sox later traded Dane Dunning to Texas for Lance Lynn, with Lynn, Giolito and López all playing a big role in 2021.

Cleveland Guardians: Traded for RHP Emmanuel Clase (Dec. 15, 2019)

Like Chicago, quite a few solid long-term extensions in Cleveland that were candidates, including Corey Kluber, Andrés Giménez and José Ramírez—each of which was announced basically hours before Opening Day, by the way, barely counting as offseason moves. But flipping Kluber to Texas and getting back Emmanuel Clase was sensational for Cleveland. Not only did Kluber pitch just one inning in 2020, but Clase has led the majors in saves in each of the past two seasons.

Detroit Tigers: Traded 1B Prince Fielder for 2B Ian Kinsler (Nov. 20, 2013)

This one was more than a decade ago, however, it was 10 offseasons ago, so it counts. And thank goodness, because Detroit didn't have any other good options, unless you want to pre-emptively declare the Colt Keith extension a huge success.

What a huge trade, though. Not only was the acquisition of Kinsler great, resulting in 17.4 bWAR over the course of four seasons, but the Tigers unloaded that bad Fielder contract right before his career dropped off a cliff. It was bad enough paying Miguel Cabrera's contract. Imagine if Detroit had also been stuck paying Fielder through 2020.

Kansas City Royals: Signed RHP Chris Young (Mar. 7, 2015)

Kansas City made two key additions to its starting rotation during the 2014-15 offseason, signing both Chris Young and Edinson Vólquez. Each made a pair of appearances in the five-game World Series victory over the New York Mets. But while Vólquez signed a two-year, $20 million deal, Young was the bargain of all bargains, signing a one-year, $675,000 contract before giving the Royals a 3.06 ERA and a solid run through the postseason.

Minnesota Twins: Traded for RHP Sonny Gray (Mar. 13, 2022)

Same as Baltimore, an honorable mention to Minnesota's decision to sign Nelson Cruz as a free agent. He finished top 10 in the AL MVP in both years of the deal he signed in Dec. 2018, posting a 1.020 OPS between those two seasons. But it was Sonny Gray who pitched five scoreless innings in leading Minnesota to its first postseason series victory in more than two decades, and Gray who would have won the AL Cy Young were it not for Gerrit Cole. He anchored the best pitching rotation in baseball in 2023.

Houston Astros: Traded for RHP Gerrit Cole (Jan. 13, 2018)

Knowing they could never afford to keep him for the long haul, the Pittsburgh Pirates put Gerrit Cole on the trade block with two years of arbitration eligibility remaining, ultimately trading him to the Astros for the quartet of Joe Musgrove, Colin Moran, Jason Martin and Michael Feliz. Musgrove ended up being solid, but nowhere near good enough to make Houston regret giving him up to get two years' worth of Cole's dominance. He made 65 regular-season starts with a 2.68 ERA and led the majors in K/9 in each season. He also made seven postseason starts with an even better 2.17 ERA.

Los Angeles Angels: Traded for SS Andrelton Simmons (Nov. 12, 2015)

In February 2014, Atlanta signed Freddie Freeman to an eight-year deal and Andrelton Simmons to a seven-year deal, planning on having that core together through 2020. But two years later, it traded Simmons to the Angels for one year of Erick Aybar and two highly touted pitching prospects who ended up amounting to nothing.

Simmons was great for his first three yearsin LA, earning MVP votes and a Gold Glove in both 2017 and 2018...while LAA still finished below .500 both years, because of course it did.

Oakland A's: Traded for RHP Chris Bassitt and 2B Marcus Semien (Dec. 9, 2014)

This was an all-time heist of a trade, with the White Sox giving up Chris Bassitt, Marcus Semien and two others for one year of Jeff Samardzija (resulting in a 4.96 ERA) and Michael Ynoa, who never came close to living up to the hype that had fizzled out long before this trade happened. Both Bassitt and Semien played six seasons for Oakland, with Semien finishing third in the 2019 AL MVP vote and Bassitt getting Cy Young votes in both 2020 and 2021.

Seattle Mariners: Signed OF/DH Nelson Cruz (Dec. 1, 2014)

Cruz's one-year deal with Baltimore and two-year deal with Minnesota weren't quite enough to be deemed best for those franchises, but his four-year deal with Seattle was great for the Mariners. From 2015-18, Cruz led all MLB hitters with 163 home runs, averaging better than 40 per year. He was worth 17.1 bWAR for the M's. It's a shame they never had enough other offensive pieces around him to make the playoffs.

Texas Rangers: Acquired OF Adolis García (Dec. 21, 2019)

Doesn't get much better than this for an offseason move. Texas scooped up García for nothing when St. Louis released him to make room on its 40-man roster for a newly acquired pitcher. And with three years of team control still to come, he has already racked up 97 home runs and 298 RBI for the Rangers, not including his record-setting 22 runs driven in during the postseason run this past October.

Atlanta Braves: Traded for SS Dansby Swanson (Dec. 9, 2015)

With an extremely honorable mention to the decision to sign Freeman to an eight-year extension before he reached arbitration, it was the trade for Dansby Swanson—who Arizona took with the No. 1 overall pick just a few months prior—that made up for the aforementioned trading away of Simmons. Atlanta sent Shelby Miller and Gabe Speier to the D-Backs for Swanson, Ender Inciarte and Aaron Blair. Miller never pitched well for the Snakes and Speier never pitched for them at all, while Swanson played well enough in Atlanta to be deemed worthy of a seven-year, $177M deal last winter with the Chicago Cubs.

Miami Marlins: Traded for RHP Sandy Alcantara and RHP Zac Gallen (Dec. 14, 2017)

What did Miami need to give up to get two of the best starting pitchers in baseball today? Just Marcell Ozuna, who did at least give the Cardinals two reasonably solid years before hitting free agency. But what a laughably lopsided deal that has become with the benefit of hindsight. The Marlins did end up trading Zac Gallen away before fully appreciating how good he would become, but they're not exactly kicking themselves for making that one-for-one swap of Gallen for Jazz Chisholm Jr.

New York Mets: Traded for SS Francisco Lindor and RHP Carlos Carrasco (Jan. 7, 2021)

New York gave up both Andrés Giménez and Amed Rosario in this deal, and ended up committing a boatload of money to Lindor a couple of months after acquiring him from Cleveland. But for a shortstop who finished ninth in the NL MVP vote in each of the past two seasons, it's a good deal, no? And though he was dreadful this past season, Carrasco was a key piece of that 101-win starting rotation in 2022.

Philadelphia Phillies: Signed OF/DH/1B Bryce Harper (Mar. 2, 2019)

The Phillies have made a lot of good offseason moves during their development into an annual contender, not the least of which was the aforementioned extension for Nola back in February 2019. But it was the signing of Bryce Harper a few days after the agreement with Nola that set in motion what the Phillies would become today. He has become the exact face of the franchise they were hoping for, including winning NL MVP in 2021.

Washington Nationals: Signed RHP Max Scherzer (Jan. 21, 2015)

It's not often that a $210M contract ends up feeling like a bargain, but Scherzer was worth every single penny to the Nationals, winning two Cy Youngs, nearly winning four others and playing a gigantic role during that 2019 World Series run. He was worth 38.9 bWAR to the Nationals and was part of the trade (along with Trea Turner) that netted the Nats their likely 2024 Opening Day battery of Josiah Gray and Keibert Ruiz.

Chicago Cubs: Signed LHP Jon Lester (Dec. 15, 2014)

Trading for Dexter Fowler in Jan. 2015 was huge for the Cubs. Both in the regular season and postseason, he was indispensable in center field. But the acquisition of Jon Lester one month prior to that trade was even bigger in the quest to break the curse. It certainly wasn't a cheap signing. That six-year, $155M deal was a big risk. In 2016, though, he almost won NL Cy Young and was phenomenal in the postseason, including his three-inning relief appearance in Game 7 of the World Series. The Cubs would have paid $300 million knowing he'd be that pivotal. Lester was also strong in 2015 and 2018.

Cincinnati Reds: Traded for RHP Luis Castillo (Jan. 19, 2017)

Castillo was traded four times before making his MLB debut, and it was Cincinnati who won that game of Prospect Hot Potato. In his five-plus seasons with the Reds, Castillo was worth 18.0 bWAR and the starting pitcher for one of the two postseason games this franchise has played in the past decade. And when the Reds decided to trade him away two summers ago, Castillo netted them Noelvi Marte, Levi Stoudt, Edwin Arroyo and Andrew Moore, which was quite the gift on his way out the door.

Milwaukee Brewers: Traded for OF Christian Yelich (Jan. 25, 2018)

During the 2014-15 offseason, the Miami Marlins signed Yelich to a seven-year extension for a total of just under $50M. But rather than keep him for the duration of the deal, they traded him to Milwaukee less than three years later for Lewis Brinson, Isan Diaz, Monte Harrison and Jordan Yamamoto—a quartet with a combined career bWAR of negative-6.8. Meanwhile, Yelich won NL MVP in his first season with the Brewers and narrowly missed winning it again in his second season.

Pittsburgh Pirates: Traded for OF Bryan Reynolds (Jan. 15, 2018)

One year away from reaching free agency for the first time in his career, the San Francisco Giants decided they couldn't wait to get their hands on Andrew McCutchen, giving the Pirates Bryan Reynolds (and Kyle Crick) for Cutch's expiring contract. It did not age well for the G-Men, who were sitting at .500 at the end of August when they traded him to the Yankees. But it worked out beautifully for the Pirates, with Reynolds playing well over the past five years and signed through at least 2030.

St. Louis Cardinals: Traded for 3B Nolan Arenado (Feb. 1, 2021)

Due diligence was done here, jotting down the trades for Paul Goldschmidt and Jason Heyward as well as the decision to give Matt Carpenter a six-year extension. But nothing was ever going to beat the highway robbery that was the Nolan Arenado trade. The Cardinals gave up a pupu platter of five players who have yet to amount to anything and got back a great hitter and one of the best gloves in the business. In his first three years in St. Louis, Arenado hit 90 home runs, was an All-Star in all three seasons and might have been NL MVP in 2022 were it not for teammate Goldschmidt winning instead.

Arizona Diamondbacks: Signed RHP Zack Greinke (Dec. 8, 2015)

In due time, this will likely be replaced by the decision to lock up Corbin Carroll on a long-term deal, which already looks incredible. But let's give that a few more years to ferment before we vault it ahead of the Greinke signing. He wasn't as good in his three-plus years with Arizona (3.40 ERA) as he was in the preceding three seasons with the Dodgers (2.30 ERA), but Greinke was outstanding in 2017 as the Diamondbacks recovered from a 93-loss 2016 campaign to become a 93-win playoff team.

Colorado Rockies: Traded for RHP Germán Márquez and LHP Jake McGee (Jan. 28, 2016)

Here's the antithesis of shocking news: There were one, maybe two viable candidates for the Rockies' spot on this list, depending on whether you're ready to declare last winter's offseason trade for Nolan Jones a big success. (Certainly looks good thus far.)

But at least Colorado made this trade with Tampa Bay eight years ago, getting both one of the best starting pitchers in franchise history and a reliever who served as the closer for a short while, all for the modest price of Corey Dickerson and Kevin Padlo.

Los Angeles Dodgers: Traded for OF Mookie Betts and LHP David Price (Feb. 10, 2020)

Same as the Nolan Arenado trade for St. Louis, quite the no-brainer pick here for the Dodgers. Even with David Price's albatross of a contract included in the deal, getting Mookie Betts for Alex Verdugo, Jeter Downs and Connor Wong was a fantastic swap for the Dodgers, and a massive part of their winning the 2020 World Series and averaging 106 wins over the past three regular seasons.

San Diego Padres: Signed 3B Manny Machado (Feb. 21, 2019)

The Dec. 2020 trades for Blake Snell and Yu Darvish worked out beautifully, but the initial 10-year, $300M contract with Manny Machado was an awesome deal for the Padres. In his first four years in San Diego, Machado hit .280 and slugged .504, nearly winning NL MVP in both 2020 and 2022. Because there was an opt-out in the deal, they re-signed him to an 11-year, $350M deal this past offseason, and that one might get pretty painful before it runs its course. But the initial signing? A+.

San Francisco Giants: Extended SS Brandon Crawford (Nov. 17, 2015)

San Francisco has signed some quality free agents (Alex Cobb, Carlos Rodón, etc.) and made some solid trades (Mike Yastrzemski, LaMonte Wade Jr., etc.) over the past 10 offseasons. But if the Giants hadn't signed Crawford to a six-year, $75M extension, they might have lost him to free agency after the 2017 season. Had that been the case, they would have missed out on both an All-Star season in 2018 and what was darn near an MVP campaign in 2021 when he anchored that 107-win squad.