What were they thinking? Phillies' 5 worst summer trades as 2021 MLB deadline approaches

In the past, the Phillies haven't determined whether they will be buyers or sellers until just before the July 31 deadline.

That apparently was the case up until Monday, when Phillies president Dave Dombrowski told John Clark of NBCSports Philly that he intends to be a buyer. The Phillies' 10-4 record this month heading into their game Tuesday against the Yankees was enough to convince Dombrowski to make a push for the NL East title.

The Phillies, at 47-45, are only 2½ games behind the first-place Mets, who just placed pitcher Jacob deGrom and shortstop Francisco Lindor on the injured list.

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The Philles can certainly use the help, whether it's a center fielder, a starting pitcher, or a reliable late-inning reliever.

But these deals don't always work out. And sometimes, the best trades are the ones that aren't made.

That was never more apparent than the early 2000s when the Phillies were reportedly considering trading Ryan Howard, who at the time was unhappy that he was stuck in the minor leagues behind Jim Thome, to the Pirates for starting pitcher Kris Benson.

Then-general manager Ed Wade was reportedly discussing a deal for Oakland A's star pitcher Barry Zito in return for prospects second baseman Chase Utley, reliever Ryan Madson and outfielder Michael Bourn.

Credit Wade for saying no. The Phillies would never have won the 2008 World Series, or five straight division crowns, had they made those trades. But they still made some bad deadline deals over the past 40 years. 

The five worst are listed below. On Wednesday, we'll have their five best deadline deals.

5. August 2020

The Phillies had the right intentions, desperately trying to fix a bullpen that was by far the worst in the major leagues.

But they struck out on each of their three trades for relievers. They acquired David Phelps from the Brewers, David Hale from the Yankees, and Brandon Workman and Heath Hembree from the Red Sox.

In the three deals, pitcher Nick Pivetta was the only player of consequence that the Phillies gave up.

It was still a disaster because Hale and Hembree each had ERAs over 12, and Workman's was 6.92 with three blown saves in eight chances.

In all, the Phillies finished last season with a club-worst bullpen ERA of 7.06, the second-worst in major-league history.

Needless to say, they missed the playoffs, none of the four relievers are still with the team, and general manager Matt Klentak lost his job.

4. July 2015

The trade came six days after Cole Hamels pitched a no-hitter. It was a fitting Phillies finale for a player who was drafted by the team in 2002 and was the ace of the 2008 World Series championship team.

But in 2015, the Phillies needed to trade Hamels because they were in the midst of rebuilding and Hamels could bring back the most in return.

So the Phillies sent Hamels and reliever Jake Diekman to the Rangers in return for six players, mostly prospects.

None panned out. The only saving grace in this trade was that catcher Jorge Alfaro was later included in the 2019 deal with the Marlins for J.T. Realmuto. Pitcher Jerad Eickhoff and outfielder Nick Williams were marginal major leaguers.

Hamels, meanwhile, reached the playoffs with the Rangers in both 2015 and 2016, then again with the Cubs in 2018. Who knows? He might return to the Phillies at some point this season.

3. July 2000

In some ways, it made sense to trade Curt Schilling.

The Phillies were well on their way to their seventh straight losing season, even with one of the best pitchers in baseball.

By then, Schilling was 33, and openly fed up with losing. Wade, not operating from a position of strength, sent Schilling to Arizona for four players who all contributed, albeit without much success.

Omar Daal, who ended up going a combined 4-19 in 2000 with Arizona and the Phillies, rebounded and went 13-7 in 2001. First baseman Travis Lee also followed up a tough 2000 season with 20 homers with 90 RBIs in 2001. Nelson Figueroa was a serviceable pitcher.

Vicente Padilla turned out to be the best of the bunch, which obviously isn't saying much. Padilla went 49-49 with a 3.98 ERA in six seasons with the Phillies.

It wasn't nearly enough to make up for the loss of Schilling, who as it turned out had several good years left. Schilling and Randy Johnson combined to form the top pitching duo in 2001 when the Diamondbacks won the World Series. Schilling then won two more World Series titles with the Red Sox.

2. July 2012

The Phillies, coming off five straight NL East crowns, were reeling at 13 games under .500 in late July. Both Ryan Howard and Chase Utley had missed significant time with injuries, and Roy Halladay was clearly pitching through pain that would end his career the following season.

The Phillies tried rebuilding on the fly by making two trades. They sent Shane Victorino to the Dodgers, and Hunter Pence, whom they acquired at the deadline the year before, to the Giants.

That was supposed to give phenom Domonic Brown a chance to play every day.

All of it failed miserably. The Phillies got little in return in either trade, with only Tommy Joseph, acquired in the Pence trade, doing anything at the major-league level. As for Brown, he had one good season in 2013, when he made the All-Star team. He was out of baseball after the 2015 season.

1. July 2002

Scott Rolen wanted out. The Gold Glove third baseman and 1997 NL Rookie of the Year turned down the Phillies' $140 million extension offer and was going to become a free agent after the 2002 season.

The fans certainly weren't sympathetic, booing Rolen constantly at home.

The Phillies, were 10 games under .500 and in last place, a huge disappointment considering that they were in contention until the final weekend of the 2001 season.

So the Phillies sent Rolen, easily their best player, to the St. Louis Cardinals in return for infielder Placido Polanco and pitchers Mike Timlin and Bud Smith.

Polanco was by far the best player in the deal, but he and David Bell were blocking a young Utley from playing every day. It wasn't until Polanco was traded in 2005 before that changed.

As for Rolen, he was quoted as saying he went to "baseball heaven." The Phillies, meanwhile, were stuck in baseball purgatory.

Contact Martin Frank at mfrank@delawareonline.com. Follow on Twitter @Mfranknfl.