It takes two to make a trade.
And it often takes years, along with a healthy bit of hindsight, to examine the ledgers and decide who got the better end of each deal.
But with some potential blockbusters looming yet this summer — the Red Wings’ Dylan Larkin already asked out of Detroit, while the jury is still out on Tarik Skubal and the Tigers’ playoff fate — we figured now is as good a time as any to look back at the recent history of major trades for this city’s four major pro sports teams.
Here’s 20 of the biggest deals from the last 30 years (prior to this summer and ignoring draft-day swaps), plus 10 more trades that left a mark over that span:
1. Jan. 30, 2021: Lions trade Matthew Stafford to Los Angeles Rams for Jared Goff, 2021 third-round pick and 2022 and ’23 first-round picks
More than five years later, it seems fair to call this one a win-win deal. With Detroit beginning another rebuild under a new regime, Stafford requested a trade and new general manager Brad Holmes landed a sizable return from the Rams. At the time, the focus was mostly on the draft capital, which Holmes managed to turn into a haul (via draft-day trades) that brought in Jameson Williams, Jahmyr Gibbs and Sam LaPorta, among others. He also found a replacement in Goff, who has racked up more than 20,000 passing yards, earned three Pro Bowl honors and led the Lions to back-to-back NFC North titles and their first playoff wins since 1991. Stafford, meanwhile, brought the Rams a Super Bowl title in his first season in Los Angeles and was the NFL MVP in 2025.
2. Dec. 4, 2007: Tigers trade Cameron Maybin, Andrew Miller, Mike Rabelo, Burke Badenhop, Frankie De La Cruz, Dallas Trahern to Florida for Miguel Cabrera, Dontrelle Willis
Dave Dombrowski was never shy about swinging for the fences as the Tigers’ president, but the 2007 blockbuster with his former team in Florida proved to be a grand slam. In Cabrera, he acquired a 24-year-old future Hall of Famer who’d go on to win two MVP awards, a Triple Crown and four batting titles in Detroit, finishing his career with more than 3,000 hits and 500 home runs. Willis struggled in his two-plus seasons in Detroit, while the top prospects Dombrowski gave up — Maybin and Miller — both went on to long, productive careers. Miller was a two-time All-Star who was a bullpen star in Cleveland’s run to the World Series in 2016.
3. Oct. 9, 1996: Red Wings trade Paul Coffey, Keith Primeau and 1997 first-round pick to Hartford for Brendan Shanahan and Brian Glynn
Shanahan wanted out of a hopeless situation in Hartford, and Primeau wasn’t happy with his role in Detroit. But the big winner in this trade was Scotty Bowman, who got the power forward he needed to help the Red Wings end their championship drought. Shanahan was a huge part of the Wings’ three Stanley Cups (1997-98, 2002), while Primeau had a solid career that ended a decade later due to post-concussion syndrome. Coffey, whose attempts to derail the trade enraged Bowman, ended up getting dealt again to Philadelphia, where the offensive-minded defenseman was on the losing end of the ’97 Cup finals. That first-round pick was Nikos Tselios, who played in just two NHL games.
4. Aug. 3, 2000: Pistons trade Grant Hill to Orlando Magic for Ben Wallace, Chucky Atkins
An abandonment turned out to be a real find for the Pistons. Hill, the Pistons’ franchise cornerstone, wanted out after six years in Detroit, and in Orlando he hoped to be part of a new “Big Three” with Tracy McGrady and Tim Duncan. But Duncan stayed in San Antonio, and Hill, a former No. 3 overall pick, played in just 200 games over the next seven seasons due to ankle problems. Meanwhile, the Pistons’ return in the resulting sign-and-trade with the Magic included Wallace, who’d become the anchor of the Pistons’ “Goin’ to Work” championship era. The four-time NBA defensive player of the year ended up a Hall of Famer and a franchise icon.
5. July 1, 2001: Red Wings trade Vyacheslav Kozlov and 2002 first-round pick to Buffalo for Dominik Hasek
Adding the “Dominator” was a stunner, no doubt. Hasek was the top goalie in the world and had just won his sixth Vezina Trophy as the NHL’s best netminder. But with the Sabres in the midst of a roster teardown, Red Wings GM Ken Holland pounced on the opportunity to add another Hall of Famer to a stacked roster that was a few years removed from back-to-back Cup wins. Hasek replaced Chris Osgood in net and backstopped another title run, posting a 1.86 goals-against average with six shutouts in the playoffs. He briefly retired after that, then returned twice more to the Wings, winning another Cup in Detroit as Osgood’s backup in the 2008 playoffs. Kozlov, who’d been part of the Russian Five in Detroit, only spent one year in Buffalo before finishing his NHL career in Atlanta.
6. Dec. 8, 2009: Tigers trade Curtis Granderson to New York Yankees, Edwin Jackson to Arizona in exchange for Max Scherzer, Austin Jackson, Phil Coke, Daniel Schlereth
Granderson was a fan favorite in Detroit, and included in his productive time in New York was an MVP-caliber year in 2011. But the return made everyone forget about that. Not coincidentally, so did the Tigers’ playoff series wins over the Yankees in 2011 and ’12. Scherzer joined Justin Verlander atop a dominant rotation over his five years in Detroit, winning a Cy Young Award and helping the Tigers to four straight division titles and a World Series appearance. Dombrowski also landed a leadoff hitter in Jackson, who was a runner-up for rookie of the year in 2010, and a reliable left-handed reliever in Coke, who pitched in nearly 300 games for the Tigers over five seasons.
7. March 23, 1999: Red Wings trade Anders Eriksson, 1999 and 2001 first-round picks to Chicago for Chris Chelios
Holland was pulling out all the stops to try to win a third straight Stanley Cup in 1999. But on a day where he acquired winger Wendel Clark from Toronto and veteran goalie Bill Ranford from Edmonton, a deal with the rival Blackhawks managed to steal the headlines. Chicago was in the midst of a fire sale and Chelios, who’d spent a decade there, wasn’t ready to play out his contract and retire. And after drawing interest from San Jose and Philadelphia, Detroit swooped in with an offer that included a contract extension. It didn’t take long for him to win over the fans, and Chelios would go on to play another decade for his third Original Six team, winning two Stanley Cups and cementing his Hall of Fame credentials. Eriksson only played one full season in Chicago, and the two first-round picks — Steve McCarthy and Adam Munro — didn’t make much of a mark, either.
8. Feb. 19, 2004: Pistons trade Zeljko Rebraca, Bob Sura, 2004 first-round pick to Atlanta Hawks and Chucky Atkins, Lindsey Hunter, 2004 first-round pick to Boston Celtics in three-way deal for Rasheed Wallace, Mike James
This trade proved to be a “guaran-Sheed” winner for Joe Dumars and the Pistons. In Wallace — a versatile, if temperamental, All-Star power forward — they added the missing piece to a championship team, and he’d remain in Detroit for five more seasons after that 2004 title. Hunter ended up re-signing with Detroit a week later and bolstered the Pistons’ bench along with James. The first-round picks turned into Tony Allen (Boston) and Josh Smith (Atlanta), though Smith would end up signing with the Pistons in free agency a decade later.
9. Sept. 11, 2002: Pistons trade Jerry Stackhouse, Brian Cardinal, Ratko Varda to Washington Wizards for Richard Hamilton, Hubert Davis, Bobby Simmons
The timing was a surprise, coming a few weeks before the start of training camp. But while Dumars took a risk in trading away a two-time All-Star and the team’s leading scorer in Stackhouse, he got a younger scoring guard in return with Hamilton. He was happy to get out of Michael Jordan’s shadow with the Wizards, and he thrived in Detroit, leading the Pistons in scoring for the next decade and helping the team reach six straight Eastern Conference finals. His No. 32 jersey is now hanging from the rafters. Stackhouse only spent two seasons in Washington and after 2003 he only started a total of 58 games the rest of his lengthy NBA career.
10. Aug. 31, 2017: Tigers trade Justin Verlander to Houston Astros for Franklin Perez, Jake Rogers, Daz Cameron
The on-again, off-again talks involving Verlander went down to the wire in the summer of 2017. And it wasn’t until the Tigers made it clear that a deal with the Chicago Cubs wasn’t going to happen — minutes before the midnight deadline — that Verlander signed off on the trade to Houston. He was dominant down the stretch for the Astros, who won the World Series that season, and Verlander went on to win two more Cy Young Awards and another World Series ring in Houston. Detroit’s return didn’t pan out as hoped for GM Al Avila, who also picked up part of Verlander’s salary in the deal. Perez, a top-50 prospect, never made it past Double A and Cameron hit .201 in three abbreviated seasons in Detroit. Rogers is the only remaining piece as the Tigers’ backup catcher.
11. Nov. 3, 2008: Pistons trade Chauncey Billups, Antonio McDyess, Cheikh Samb to Denver Nuggets for Allen Iverson
If Dumars could have this one back, he would. Trading Billups proved to be a mistake at the end of the Pistons’ six-year run as NBA title contenders. Billups, the 2004 NBA Finals MVP, was the team leader, but Dumars opted to unload his contract and then sign Hamilton to an extension instead, while trading for Iverson and the polarizing former league MVP’s expiring deal. Iverson’s lone season in Detroit proved to be a disaster on and off the court, and while the Pistons won just 39 games and got swept by LeBron James and Cleveland in the first round, Billups went to the conference finals again in Denver.
12. Jan. 29, 2018: Pistons trade Avery Bradley, Tobias Harris, Boban Marjanovic, 2018 first-round pick, 2019 second-round pick to Los Angeles Clippers for Blake Griffin, Brice Johnson, Willie Reed
Seven years into his tenure as Pistons owner — and 10 years removed from the franchise’s last playoff win — Tom Gores gave the OK for a blockbuster deal to land a long-sought star player in Detroit. Blake Griffin looked the part initially, but knee problems that began late in his second season here muted the impact of the deal and three years after he arrived the Pistons bought out the remainder of his contract. Harris ended up returning in free agency in 2023, helping the Pistons finally end their playoff drought. But that first-round pick (12th overall) was used to select Michigan State’s Miles Bridges, but was traded to Charlotte on draft night for the No. 11 pick, Shai Gilgeous-Alexander, the two-time reigning NBA MVP.
13. July 23, 2012: Tigers trade Jacob Turner, Rob Brantly, Brian Flynn to Florida for Anibal Sanchez, Omar Infante
Dombrowski traded away the team’s No. 1 prospect in Turner, but the return helped the Tigers make a pair of deep postseason runs. Sanchez posted a 1.77 ERA in Detroit’s World Series run in 2012, then led the AL in ERA in 2013 after signing a five-year, $80 million extension. Infante became the Tigers’ starter at second base in ’13 and batted .318 with a .795 OPS. Turner never panned out, winning just 14 games in an injury-riddled, eight-year MLB career.
14. June 29, 1994: Red Wings trade Steve Chiasson to Calgary for Mike Vernon
The Red Wings knew they had a team capable of winning the Stanley Cup. But after a disastrous Game 7 loss to San Jose in the first round of the 1994 playoffs — sealed by Osgood’s puckhandling gaffe — Bowman wanted some veteran insurance in net. The Wings had pursued Vernon for more than a year, but finally landed the former Cup winner (1989) and five-time All-Star that summer, giving up Chiasson, an offensive defenseman who was an alternate captain in Detroit. Vernon backstopped the Wings to the Cup final in 1995, then served as Osgood’s backup in the ’96 playoffs. But Bowman turned back to his veteran in ’97, and Vernon went 16-4 with a .927 save percentage in the postseason run as the Wings ended their 42-year championship drought. He was traded to San Jose later that summer for a pair of second-round picks.
15. July 9, 2023: Red Wings trade Dominik Kubalik, Donovan Sebrango, 2024 conditional first-round pick and fourth-round pick to Ottawa for forward Alex DeBrincat
Ottawa GM Pierre Dorion thought he’d hit the jackpot when he paid a ransom to add Debrincat, a 40-goal scorer, to his young core in the summer of 2022. But a year later, after the star winger had made it clear he wouldn’t sign an extension to stay with the Senators, Dorion was forced to take a lesser return from Detroit, DeBrincat’s hometown team. Steve Yzerman gave up an expendable winger in Kubalik, a middling prospect (Sebrango) and a conditional first-round pick that ended up the 25th overall selection (Dean Letourneau), and then signed DeBrincat to a four-year, $31.5 million extension. Debrincat has scored 107 goals in his three seasons with the Wings, including a team-best 41 in an 85-point season in 2025-26.
16. Feb. 26, 2008: Red Wings trade 2008 second-round pick, 2009 fourth-round pick to Los Angeles Kings for Brad Stuart
Stuart was arguably the final piece to another Stanley Cup in Detroit, acquired at the deadline from the Kings to shore up the Wings’ blueline. Stuart joined Niklas Kronwall to form a reliable second defensive pair behind Nick Lidstrom and Brian Rafalski down the stretch. And he proved to be far more than a playoff rental, signing a four-year, $15 million extension to remain that summer. The second-round pick (Peter Delmas) never played in the NHL, but the fourth-rounder became Ben Chiarot, who ended up in that same second-pair defensive role in Detroit some 15 years later.
17. March 18, 1997: Red Wings trade future considerations to Toronto for Larry Murphy
Scapegoats are priced to sell, apparently. And in Murphy, the Red Wings got a true bargain, because the floundering Maple Leafs were looking to unload their highest-paid player in a salary dump. Leafs GM Cliff Fletcher found a trade partner in Bowman, who’d won a couple Stanley Cups in Pittsburgh with Murphy, a veteran defenseman feeling the wrath of fans in Toronto that winter. And the Wings found an ideal partner for Lidstrom, as Murphy’s veteran savvy and offensive skill helped solidify the blue line in Detroit as the Wings won back-to-back Cups. The Hall of Famer even re-signed and played until he was 40 at the end of the 2000-01 season.
18. Nov. 20, 2013: Tigers trade Prince Fielder to Texas Rangers for Ian Kinsler
Owner Mike Ilitch made a bold move in free agency in 2012, instructing his front office to target Fielder as a replacement for Victor Martinez, who’d been lost for the season to an ACL injury. The resulting nine-year, $214 million deal was palatable in Year 1, but after Fielder’s disappointing playoff performance in 2013, it was already time to move on. Lucky for the Tigers, they found a taker in Texas, who offered up a three-time All-Star second baseman in Kinsler, who had four productive seasons in Detroit. The Tigers also picked up $30 million of the remaining $168 million due to Fielder, who retired after three injury-plagued seasons for the Rangers.
19. July 31, 2014: Tigers trade Austin Jackson to Seattle, Drew Smyly and Willy Adames to Tampa Bay for David Price
Dombrowski made another blockbuster at the deadline, adding Price, another former Cy Young winner, to a stacked rotation that already featured Verlander and Scherzer. Price pitched well for the Tigers down the stretch and helped them clinch a fourth straight division title, but that team was swept by Baltimore in the ALDS. And after earning another All-Star nod in 2015, Dombrowski then dealt Price to Toronto that summer in a deadline selloff that marked the end of his tenure as president in Detroit. Smyly went 52-54 pitching for six teams over the next decade, Jackson batted .270 for six teams over four years and Adames went from top prospect in Tampa to a starting shortstop who signed a seven-year, $182 million deal with San Francisco two years ago.
20. Oct. 14, 2008: Lions trade Roy Williams and 2010 seventh-round pick to Dallas Cowboys for 2009 first-, third-, and sixth-round picks
This was the first big test for interim GM Martin Mayhew after Matt Millen was fired as team president in September. And with the haul he got for Williams, the Lions’ disgruntled No. 1 receiver, the deal goes down as one of the worst in Cowboys history. Dallas signed Williams to a $54 million contract extension, but he caught just 94 passes in 40 games before Dallas released him in 2011. Mayhew used the first-round pick on tight end Brandon Pettigrew, who caught 301 passes in seven seasons for the Lions, while the other picks — receiver Derrick Williams and running back Aaron Brown — made little impact.
30-for-30
Here’s 10 more trades that didn’t make the list:
1. March 19, 2020: Lions trade Darius Slay to Philadelphia for 2020 third- and fifth-round picks
2. Nov. 2, 1999: Tigers trade Frank Catalanotto, Francisco Cordero, Bill Haselman, Gabe Kapler, Justin Thompson to Texas for Juan Gonzalez, Danny Patterson, Gregg Zaun
3. July 30, 2011: Tigers trade Francisco Martinez, Charlie Furbush, Casper Wells, Chance Ruffin to Seattle for Doug Fister, David Pauley
4. March 11, 2003: Red Wings trade Sean Avery, Maxim Kuznetsov, 2003 first-round pick, 2004 second-round pick to Los Angeles for Mathieu Schneider
5. Jan. 8, 2004: Tigers trade Ramon Santiago, Juan Gonzalez (not that one) to Seattle for Carlos Guillen
6. Nov. 1, 2022: Lions trade T.J. Hockenson, 2023 fourth-round pick, 2024 fourth-round pick to Minnesota for 2023 second-round pick, 2024 third-round pick
7. March 1, 2023: Red Wings trade Filip Hronek and 2023 fourth-round pick to San Jose for 2023 first- and second-round picks
8. April 12, 2021: Red Wings trade Anthony Mantha to Washington for Jakub Vrana, Richard Panik, 2021 first-round pick and 2022 second-round pick
9. March 10, 2015: Lions trade 2015 fourth- and fifth-round picks to Baltimore for Haloti Ngata and 2015 seventh-round pick
10. Oct. 30, 2018: Lions trade Golden Tate to Philadelphia for 2019 third-round pick
john.niyo@detroitnews.com
@JohnNiyo
This article originally appeared on The Detroit News: Niyo: Taking a look at Detroit’s 20 biggest trades in the last 30 years
Reporting by John Niyo, The Detroit News / The Detroit News
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By John Niyo, The Detroit News | USA TODAY Network
