It has been quite some time since the Phillies have been in postseason contention. Okay, well maybe three seasons isn't that many, but Phils fans don't have too much to look forward to in terms of potential playoff scenarios over the coming years. The team really began their push to five straight NL East titles, a World Championship and two NL Championships from within. Ryan Howard, Cole Hamels, Chase Utley, Jimmy Rollins, Pat Burrell among others were drafted by the Phillies and got to contribute to this success. Low-risk acquisitions including Jayson Werth, Pedro Feliz and Geoff Jenkins also helped the Phillies compete for the World Series.

Following the 2008 championship season, the Phillies management shifted to Ruben Amaro's control. Amaro didn't have too much of a reputation before being named GM, but as we all know, that has changed. Whether it be questionable contracts or smug comments, Amaro has been scrutinized across Philadelphia recently due to the Phils fall from grace over the past few years. A big part of Amaro's tenure as GM thus far was sacrificing the future for winning now. Well, a few years ago kind of now. Ruben made deals for a trio of big name pitchers and also some other players he had hoped would bring the city another championship. Unfortunately, that plan didn't work out well and now the Phillies lack depth in the farm.

While we know that prospects are never a "for sure" thing, Amaro has certainly parted ways with a lot of high-ceiling talent while also acquiring numerous prospects in return. Let's take a look at the notable trades Amaro has made during his tenure, specifically what prospects have panned out and which ones never lived up to the hype.

December 15th, 2009 - Phillies acquire Roy Halladay from the Blue Jays in exchange for Travis d'Arnaud, Kyle Drabek and Michael Taylor

Kyle Drabek - Once deemed the "untouchable" prospect in the Phillies organization, Drabek has failed to become any sort of contributor to the Blue Jays since they acquired him in 2009. Drabek was the cornerstone of this trade from the Phillies side and luckily for them, he hasn't done much to make them regret trading him. He made his big league debut in September of 2010, but struggled in the Jays rotation in 2011, posting a 6.06 ERA in 18 games (14 starts) before being sent back to the minors. Drabek made 13 starts for Toronto in 2012 before needing his second Tommy John surgery. He posted a 4.67 ERA before getting hurt in 2012. This season in Triple-A, he posted a 4.18 ERA in 99 innings pitched, giving up 116 hits and 30 walks. He pitched three innings of relief for the Blue Jays at the end of 2014, giving up no runs while striking out five. Time is running out for Drabek to show if he still has anything left in the tank. Two Tommy John surgeries sure don't make things any easier.

Travis d'Arnaud - drafted in the first round of the 2007 draft, d'Arnaud seems the be the lone prospect in this deal that has developed into a serviceable Major League player. After a few seasons in Toronto's minor league system, d'Arnaud was flipped to the Mets in a trade that sent R.A. Dickey to Toronto. He was called up to the Mets in August 2013 and has stuck with the big league club since. He will likely be the Mets starting catcher in 2015. In 108 games during the 2014 season, d'Arnaud hit .242 with 13 homers and 41 RBI's. He caught 19% (14-for-58) of base stealers.

Michael Taylor - The Phillies were hesitant to trade either Taylor or Domonic Brown, but they ended up trading Taylor in the Halladay deal. He was immediately dealt to Oakland by the Blue Jays in exchange for Brett Wallace. Taylor is what you would call a quadruple-A player. He has torn up the minor leagues but it never transitioned over to success at the big league level. Before being traded, Taylor slashed .320/.395/.549 with Reading and Lehigh Valley in 2009. He hit 20 homers and drove in 84 runs. In his brief major league stints with Oakland and the White Sox, Taylor has hit .167 (17-for-102) with 35 strikeouts. This season in Triple-A with Sacramento (OAK) and Charlotte (CHW), Taylor hit .275 with 11 homers and 69 RBI's. Over his minor league career, spanning parts of eight years, he's hit .290 with 108 homers and 568 RBI's.

Review: The Phillies obviously got the better end of this deal. Despite Domonic Brown's significant regression, he has turned out to be a better player than Taylor while Drabek never panned out at all. Meanwhile, Travis d'Arnaud would have been nice to keep for the Phils as they lack options behind the aging Carlos Ruiz.

Though he didn't end up winning a World Series with the Phillies, Roy Halladay had a hell of a career in Philadelphia, posting a record of 55-29 to go along with a 3.25 ERA. He will be most remembered for his perfect game against the Marlins and his postseason no-hitter against the Reds. In 2010, Halladay won the NL Cy Young Award, adding to the AL one he earned in 2003 with the Blue Jays.

Stay tuned for Part II of the series, analyzing the prospects involved in both Cliff Lee trades