Before there was CC Sabathia, there was Sutton, who was already considered a future Hall of Famer when the Brewers added him for the 1982 playoff push. He went 4-1 with a 3.29 ERA in seven regular season starts, the biggest a duel with Baltimore's Jim Palmer on the final day of the season, with the American League East crown on the line. Boosted by two Robin Yount home runs, Sutton worked eight innings and limited the Orioles to two runs for the Brewers' first division title.
2. July 7, 2008: Brewers receive CC Sabathia from the Indians for Matt LaPorta, Zach Jackson, Michael Brantley and Rob Bryson.
Sabathia strapped a postseason-starved franchise on his broad back, going 11-2 with a 1.65 ERA in 17 regular season starts after the trade and leading the Brewers to their first playoff appearance in 26 years. He made his final three starts on three days' rest and, despite pitching only three months in the National League, led the circuit with seven complete games, including a four-hit gem in the regular-season finale that clinched the Wild Card.
"Big game, big moment, big man," Brewers pitching coach Mike Maddux said. "It was the right situation."
LaPorta was the Brewers' top prospect at the time, but has struggled to get established in Cleveland. The best player in Cleveland's haul proved to be Brantley, who was a player to be named in the original swap.
3. June 15, 1977: Brewers receive Mike Caldwell from the Reds for Rick O'Keefe and Garry Pyka.
The Brewers were one year away from their breakthrough season when they acquired the left-handed Caldwell, who would win 22 games in 1978 and go on to become the Brewers' record holder for complete games (81) and second in club history with 102 wins and 1,604 2/3 innings. He pitched for the Brewers through 1984.
4. July 27, 2012: Brewers receive Jean Segura, Johnny Hellweg and Ariel Pena from the Angels for Zack Greinke.
If Greinke hadn't been acquired in the offseason, he would be on this list. When it was clear he would not re-sign with the Brewers, general manager Doug Melvin pitted the Angels against the Rangers -- AL West rivals -- for Greinke's services, and wound up with the Brewers' shortstop of the future -- Segura, who was an All-Star the following season -- and two top pitching prospects. Time will tell how those pitchers pan out, but considering the Angels missed the postseason and then lost Greinke to free agency, the Brewers look like clear winners in the deal.
5. Aug. 31, 1996: Brewers receive Jeromy Burnitz from the Indians for Kevin Seitzer.
Burnitz was 27 at the time of the trade and went on to play parts of six seasons with the Brewers, ranking ninth in Brewers history with 165 home runs. He was an All-Star in 1999.