No. 1: Phillies sign Pete Rose on Dec. 5, 1978
Widely considered the team's best Winter Meetings deal, the Phillies inked hitting legend Pete Rose to a four-year contract on Dec. 5, 1978. Beating out many suitors, the Phils made the 38-year-old the highest-paid player at $800,000 a year.
After the Phillies lost three straight NLCS appearances from 1976-78, signing Rose was a move designed to help put them over the top and finally win a World Series. And boy, did it pay off. He spent five seasons in Philadelphia, helping the team win the 1980 Fall Classic.
The all-time hits leader collected 826 of his 4,256 hits as a Phillie, including his record-setting 3,631st hit in 1981 to pass Stan Musial as the all-time NL hits leader. He earned four All-Star nods from 1979 to 1982, and won his lone career Silver Slugger in 1981.
In his 1979 Phillies debut season, he hit .331 with an .848 OPS, which included an NL-leading .418 on-base percentage.
His 1980 regular season wasn't as impressive; he hit .282 but led the league in doubles with 42. However, in the postseason he did what the front office had hoped the proven playoff performer would do. Rose hit .326 with a .780 OPS over 11 games on his way to his third World Series title and, more importantly, the team's first.
He continued performing on the biggest stages into his 40s with the Phillies. He slashed .300/.364/.350 in the 1981 NLDS and then put together a .344/.382/.375 line in the 1983 playoffs, which saw the Phillies win the NL pennant and head to the World Series again.
Rose finished his Phillies career with a .291 batting average and .726 OPS in 745 games, but his lasting legacy in the city is the franchise's first World Series title.