Phillies’ 6 biggest MLB Winter Meetings moves

The MLB Winter Meetings always bring a flurry of moves across the league. From minor transactions to major franchise-altering deals, there's no lack of excitement when the top team executives get together with players and their agents for four days of wheeling and dealing.

It's hard to say what the Phillies' front office plans on doing at this year's Winter Meetings. The team has some areas of need, so president of baseball operations Dave Dombrowski and general manager Sam Fuld should be active in Nashville. It's unlikely that they'll make a franchise-altering move this time around. But you never know.

The Philadelphia Phillies have had their fair share of significant Winter Meetings over the years, although not all moves are completed at the December convention. Sometimes it's just the groundwork that's laid for future signings and trades.

The Phillies have worked on some big deals at the Winter Meetings that didn't come to fruition until later. Think of the famous Roy Halladay trade in 2009, when they finalized the deal with the Toronto Blue Jays about a week after the Winter Meetings concluded. And then there was Bryce Harper's February 2019 free agent signing, which was kick-started the preceding December when the Phillies emerged as one of the frontrunners in the Harper sweepstakes.

That being said, here are six of the franchise's biggest deals to happen during the Winter Meetings.

First up, an 11-year contract that may yet prove to be one of the biggest Winter Meetings signings in franchise history.

No. 6: Phillies sign Trea Turner to an 11-year deal on Dec 5 , 2022

The Phillies' most recent big Winter Meetings signing was only a year ago. Although for Trea Turner, his first season in Philadelphia might have felt more like a decade with the ups and downs he went through.

Fresh off their World Series defeat at the hands of the Houston Astros, the Phillies landed one of the biggest free agents on the market when they inked Turner to an 11-year, $300 million contract. It's a deal that will see him in red pinstripes through the 2033 season, in theory.

At the time, the move was deemed a massive success for Dombrowski and Fuld. About halfway through the 2023 season, however, the tide had turned as the two-time All-Star shortstop struggled through the worst season of his illustrious career with a paltry .247 batting average and .687 OPS at the All-Star break.

As it turned out, once Turner locked in, he helped catapult the Phillies to a 90-win season and the top Wild Card spot before helping guide them to within a couple of victories of the World Series. It wasn't the outcome many had hoped for (or assumed) when he was first signed, as a second consecutive trip to the Fall Classic was on everyone's minds.

There's still plenty of time for Turner to prove his Winter Meetings signing to be an even bigger franchise move, with the team's core poised for another few years of deep playoff runs. If he helps capture the Phillies' next title, the signing may be higher up the next iteration of this list.

NEXT: Another recent Winter Meetings signing added a top-end starter to the rotation.

No. 5: Phillies sign Mets' free agent Zack Wheeler on Dec 9 , 2019

Another free agent signing from more recent memory is the 2019 deal with ace pitcher Zack Wheeler. On Dec. 9, Fuld's predecessor Matthew Klentak inked the former New York Met to a five-year, $118 million contract, leading many to declare the Philadelphia Phillies as one of the winners of that year's Winter Meetings.

While the Phillies didn't make the postseason in his first two years in Philadelphia, it wasn't for lack of anything Wheeler did.

After going 4-2 with a 2.92 ERA in 11 starts during the COVID-shortened 2020 season, he came through for his new team in a big way in 2021. He pitched to a 14-10 record with a 2.78 ERA, led the Majors with 213 1/3 innings, and led the National League with 247 strikeouts. The right-hander finished second in Cy Young Award voting, was named to his first All-Star team, and even received MVP votes.

Paired with Aaron Nola, Wheeler and his 2.82 ERA helped carry the 2022 Phillies into the postseason and all the way to the World Series. Unfortunately, after a great run through the Wild Card, NLDS, and NLCS, he fell apart in the World Series and lost both his starts against the Astros with a 5.23 ERA.

In 2023, it seemed like the now 33-year-old was determined to make up for his failings the previous year. He was brilliant through his 13-6 campaign, finishing with the best fWAR (5.9) of all MLB pitchers. He finished sixth in Cy Young voting and earned his first Gold Glove Award.

Wheeler was absolutely brilliant in the playoffs this past October. He led the way for the Phillies' rotation with a 3-0 record, a 1.95 ERA, and a 0.72 WHIP with 35 strikeouts in 27 1/3 innings. That included his seven-inning, eight-strikeout gem in Game 5 of the NLCS against the Arizona Diamondbacks:

Wheeler is heading into his final year of the deal in 2024, and although there's been chatter about a possible extension, at this point, he has one more season to prove his Winter Meetings signing belongs higher on this list.

NEXT: A Winter Meetings robbery brought one of the franchise's top outfielders over from the White Sox.

No. 4: Phillies trade for Johnny Callison on Dec. 9, 1959

In one of the shrewdest Winter Meetings trades in Phillies history, general manager John Quinn swiped Johnny Callison from the Chicago White Sox in 1959 for Gene Freese, who spent all of one season in Chicago. Callison went on to become a mainstay in right field for the Phillies for 10 seasons and ended up as one of the top outfielders in franchise history.

Initially very high on the 20-year-old, the White Sox gave up on Johnny Callison after just 67 games over two seasons and a .220 batting average. The Phillies, who had finished last in the National League in 1959 with a 64-90 record, were content to let the young outfielder figure it out.

And figure it out he did.

After a couple of years in Philadelphia, Callison put together an All-Star season in 1962. He hit .300 with an .854 OPS, hit 23 home runs, drove in 83, led the NL with 10 triples, and earned MVP votes. His breakout campaign coincided with the Phillies climbing out of the basement of the NL standings, back to a respectable 81-80 record.

Callison put together another pair of All-Star seasons in 1964 and 1965, and while he never hit for that kind of average again, he discovered his power stroke. In 1964, he hit 31 home runs, drove in 104, and scored 101 times. He was second in MVP voting and the Phillies challenged for the NL crown, finishing 1.0 game behind the first-place St. Louis Cardinals.

He even hit a walk-off three-run homer in the 1964 All-Star game:

In 1965, the left-handed slugger hit a career-high 32 long balls, had 101 RBI, scored 93 runs, and led the Majors with 16 triples.

The dependable right fielder was no slouch with the glove, either. He was one of the top fielders in his prime and led the NL in outfield assists from 1962 through 1965. He led all right fielders with the highest range factor per game five times and finished in the top four in fielding percentage among right fielders in seven of his 10 seasons in Philly.

Over his 1,432 games as a Phillie, Callison accrued a 34.7 fWAR, which stands as the 11th-highest total among position players in team history, and seventh among outfielders. He finished his tenure in Philadelphia with a .271 batting average, .795 OPS, 1,438 hits, 185 home runs, 666 RBI, and 774 runs scored.

He was traded to the Chicago Cubs after the 1969 season and was enshrined in the Phillies Wall of Fame in 1997.

NEXT: A rejected Rule 5 Draft pick who reached the pinnacle of the sport in Philadelphia.

No. 2: Phillies acquire Tug McGraw from Mets on Dec. 3, 1974

In another Winter Meetings move that saw the Phillies claim a division rival's player, Philadelphia traded for Tug McGraw from the New York Mets on Dec. 3, 1974.

The left-handed reliever had spent nine seasons in New York before being acquired by the Phillies, along with Don Hahn and Dave Schneck. The Phillies sent Del Unser, John Stearns, and Mac Scarce back in what turned out to be a winning deal for general manager Paul Owens.

Known for his larger-than-life personality, McGraw and his screwball spent 10 seasons in Philadelphia, where he threw 722 innings of 3.10 ERA relief, finishing with a 49-37 record and 94 of his 180 career saves.

The "Ya Gotta Believe" mantra-toting southpaw made a big first impression with his new team, being named to his second-career All-Star game in his 1975 Phillies debut season. He threw a whopping 102 2/3 innings over 56 appearances, converted 14 saves, and kept a tidy 2.98 ERA and a 1.17 WHIP.

Already a World Series champion with the 1969 Mets, McGraw made playoff appearances in 1976, 1977, and 1978 with the Phillies before finally helping to secure the franchise's first World Series in 1980. He also pitched in the 1981 postseason.

That 1980 championship season was McGraw's best with the Phillies. He pitched 92 1/3 innings over 57 games, recorded 20 saves, and ran a 1.46 ERA and a 0.92 WHIP. He finished fifth in Cy Young Award voting and even earned MVP votes. In the World Series, he made four appearances with a 1.17 ERA and struck out 10 in 7 2/3 innings, registering two saves.

How big was this Winter Meetings trade? McGraw got the final out of the Fall Classic that year.

NEXT: A Winter Meetings free agent signing that brought the all-time hits leader and a World Series to Philadelphia.

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.

More popular Philadelphia Phillies news and analysis