The MLB Winter Meetings have often been a pivotal time for the Detroit Tigers to make franchise-altering moves. Since 1995, the Tigers have used the meetings to swing several impactful acquisitions. Below, we highlight three of the most successful and memorable Winter Meetings deals Detroit has made, which all came in a short period of time.

1. December 2007 – Blockbuster Trade for Miguel Cabrera

In one of the most stunning Winter Meetings deals ever, the Tigers acquired 24-year-old Miguel Cabrera (along with pitcher Dontrelle Willis) from the Florida Marlins for a package of six prospects, including former first-round picks Cameron Maybin and Andrew Miller. This December 2007 trade instantly gave Detroit a superstar in his prime.

Cabrera lived up to the hype and then some, he became the face of the franchise, winning two AL MVP awards and even capturing the Triple Crown in 2012 (the first in MLB in 45 years) as a Tiger.

Over his Detroit tenure, Cabrera cemented himself as a future Hall of Famer with milestones like 3,000 hits and 500 home runs, and he anchored four straight division-winning teams in the 2010s. This franchise-altering trade, pulled off by GM Dave Dombrowski at the 2007 Winter Meetings, is widely regarded as the Tigers’ greatest modern-era offseason move.

2. December 2009 – Granderson Three-Team Swap Brings Max Scherzer

Two years after landing Cabrera, Detroit made another bold Winter Meetings transaction in 2009, this time a three-team trade with the Yankees and Diamondbacks. In that deal, the Tigers parted with beloved center fielder Curtis Granderson (to New York) and starter Edwin Jackson (to Arizona) in order to net a haul of young talent headlined by right-hander Max Scherzer, center fielder Austin Jackson, and lefty reliever Phil Coke.

Scherzer, a former first-round pick, soon developed into an ace alongside Justin Verlander – he won an AL Cy Young Award in Detroit and helped the Tigers to multiple playoff runs. Austin Jackson became the Tigers’ leadoff hitter and a standout defensive center fielder for several years, while Coke contributed in the bullpen.

This savvy “retool on the fly” at the 2009 Winter Meetings was initially painful for fans (losing Granderson), but it paid huge dividends: Detroit gained multiple cost-controlled core players, including a future Cy Young winner in Scherzer.

3. December 2005 – Signing Kenny Rogers and Todd Jones Sparks a Pennant

Following a 119-loss season in 2003, the Tigers were aggressive in the 2005 Winter Meetings and signed two veteran pitchers, starter Kenny Rogers and closer Todd Jones, each to two-year contracts. These moves were somewhat under-the-radar at the time, but they proved transformational for the young Tigers club. In 2006, Rogers won 17 games and was a steadying ace for the rotation; he even threw 23 consecutive scoreless innings during that postseason while leading Detroit to the World Series. Jones, meanwhile, reclaimed the closer’s role in Detroit and saved 37 games in 2006, as the Tigers earned their first World Series appearance since 1984.

The veteran duo’s experience and leadership were instrumental in Detroit’s remarkable turnaround from cellar-dwellers to American League champions. The 41-year-old Rogers famously dominated that postseason (with three scoreless playoff starts), and Jones shut the door on countless wins, making these 2005 Winter Meetings signings two of the most impactful free-agent pickups in Tigers history.

Dombrowski kept things interesting

From blockbuster trades that brought in franchise icons to free-agent signings that filled crucial needs, the Tigers have enjoyed some truly successful Winter Meetings in the past few decades, which all came under Dave Dombrowski’s watch.

The three moves above, landing Miguel Cabrera, adding Max Scherzer (and others) via the Granderson trade, and signing Rogers and Jones, all led directly to on-field success and memorable eras in Tigers history. They stand out as prime examples of Detroit “winning” the Winter Meetings and changing the trajectory of the franchise in the years that followed.