Great Rule 5 picks, one really bad trade, and the Phillies at the Winter Meetings

The MLB Winter Meetings is a time when all owners and general managers come together and discuss the state of the league. It’s also reminiscent of July 31, where you may see some of baseball biggest names get dealt in the blink of an eye.

Some of the Phillies’ biggest moves in recent history came right after the Winter Meetings. The two of note include the trade for the late Roy Halladay from the Blue Jays (Dec. 16, 2009) and the signing of Cliff Lee almost a year later to the day, when he spurned the Rangers and Yankees and chose the Phils.

The Phillies haven’t been known to make blockbuster moves during the Winter Meetings, but there have been a few smaller acquisitions. Here’s a look at some of the deals they’ve made at past Winter Meetings:

Ruben Amaro Jr. finally succumbed to his “win now” mode, as Rollins was the first of the core players of 2007-11 to be traded. The move represented the end of an era for Philadelphia, and the double play combination of Rollins and Utley would never be seen again … in a Phillies uniform, that is. Utley would reunite with Rollins in Los Angeles in August 2015. Carlos Ruiz was traded to the Dodgers in August the following season, Ryan Howard remained with the Phillies until his contract expired in 2016, and Cole Hamels was traded to Texas at the trade deadline in 2015.

The Marlon Byrd deal at the Winter Meetings in 2014 looked insignificant at the time. Marlon Byrd for Ben Lively? Who’s Ben Lively? Byrd seemed to be traded to a new team every year, so he didn’t have much value. But, much to the surprise of many, Lively pitched well in the Phils’ minor league system and started a chunk of games for the big club, holding his own. While Lively doesn’t resemble an all-star pitcher, his ceiling is as a serviceable starter in the majors. That’s not bad for a then-36-year-old outfielder who played for 10 teams in his career.

The Phillies culminated a busy 2014 Winter Meetings by drafting Odubel Herrera from Texas in the Rule 5 draft. He’s easily been the best player on the team the last three seasons and was rewarded with a five-year, $30 million contract extension last December, with club options in 2022 and 2023.

In 2014, the trade of Jimmy Rollins signaled the end of an era. The selection of Shane Victorino from the Dodgers’ organization in 2004 signaled the beginning of an era. The center fielder played parts of eight years with the Phillies and was considered a sparkplug for the 2008 World Series championship team. He went to two all-star games, won two gold gloves in Philadelphia, and most importantly, brought home that long awaited parade down Broad Street. Can’t ask much more than that from a Rule 5 pick.

This was the first big move conducted by the current regime of General Manager Matt Klentak and President Andy MacPhail. With the new front office wanting to put its own stamp on a lengthy rebuild, they considered Giles expendable with the team years away from competing. The centerpiece of the trade was Velasquez, who the Phillies hope can morph into a top-of-the-line starter, but injuries and control issues have raised some questions about the 25-year-old’s future. Eshelman was arguably the Phillies’ best pitcher in the minors this season, posting a 2.23 ERA for Lehigh Valley in 18 starts. The right-hander is expected to pitch in the big leagues at some point this year. The Phillies were also hoping that the change of scenery for Mark Appel, the former No. 1 overall pick of the Astros in 2013, would do him some good. It hasn’t as injuries and poor performance has plagued the once highly touted pitcher. The Phillies removed him from the 40-man roster  last month. Oberholtzer was the definition of a throw-in.

The Phillies traded away five players for 24-year-old Von Hayes, a burgeoning star in Cleveland. His first two seasons for the Indians were so-so, hitting .252 with 15 home runs and 99 RBI in 193 games. He was a career .272 career hitter for the Phillies and made an all-star-game appearance in 1989, seven years after the trade was made. Hayes wasn’t a bad player, but he didn’t live up to the hype of the “five for one,” which is basically what he’s known as in eyes of Phillies fans.

The Phillies traded Hayes almost nine years later to the day, to the California Angels for Kyle Abbott and Ruben Amaro Jr.

That player to be named later happened to be Gio Gonzalez. The Phillies traded away Gonzalez, who has a 3.64 ERA and 1,600 strikeouts over a 10-year career that’s still going strong, for Garcia, who was 1-5 with a 5.90 ERA in 11 starts as a Phillie. Floyd, meanwhile, put up a 4.22 ERA over seven years and 1,042 innings with the White Sox.

Yeah, this trade sucked.