Hopefully, whoever Scott Proefrock and the Phillies draft tonight won't make a future version of this list. Image Credit: Howard Smith-USA TODAY Sports

MLB Draft: The worst first round draft picks in Philadelphia Phillies history

Earlier I provided a list of the five best first round draft picks in Philadelphia Phillies history. The Phillies have also made their share of mistakes in the first round. Here is a list of the five worst:

5. Greg Golson

John Mayberry Jr.: Better than Greg Golson. Image Credit: Bill Streicher-USA TODAY Sports

The Phillies chose a “toolsy” outfielder named Greg Golson in the first round of the 2004 draft. By the end of the 2008 season, they had become frustrated with his lack of development.

One of Ruben Amaro‘s first moves as general manager was to trade Golson to the Rangers in exchange for one of their first round picks who had similarly failed to meet expectations. And thus began the John Mayberry era in Philadelphia.

Six years later, the Phillies have easily been the winner of that deal. Mayberry may not be a superstar (and the word “may” is really unnecessary there), but he’s made some contributions in the major leagues. On the other hand, playing parts of four seasons, Golson never hit a home run in the major leagues.

My new rule of thumb: If you are ever traded for John Mayberry, and the team that gets you is the loser of that deal, then you merit inclusion in some sort of “worst of” list.

4. Brad Brink

The Phillies scouting department in the late 1980’s was really good at one thing. They were excellent at acquiring pitchers who would suffer injuries soon after joining the organization.

Brink – their first round pick in 1986 – was the poster child of this phenomenon, as I believe he hurt himself signing his contract. He eventually managed to stay healthy enough to pitch (poorly) in the majors, but the multitude of ailments sapped him of whatever skills the scouts once found appealing.

The Phillies probably should have played a little worse in 1985 to get a pick higher than seventh. The top six picks in the 1986 draft included Greg Swindell, Matt Williams, and Gary Sheffield.

3. Chad McConnell

Before the 1992 draft, the Phillies had been thought to be targeting two guys named Chad: Chad Mottola and Chad McConnell. The Reds ended up taking Mottola earlier in the draft, and he was a disappointment for them. He only played in 35 games before bouncing around the majors for a bit. And yet, compared to McConnell’s career, Mottola was a rousing success.

The Phillies tried to push McConnell to the majors aggressively, but he was never able to hit well enough to justify their faith in him. He never made it higher than Double A.

When your first round draft pick can’t even make it to Triple A, he thoroughly qualifies as a bust.

2. J.D. Drew

An appealing target for Phillies fans. (Image source)

An appealing target for Phillies fans. (Image source)

And speaking of Triple A…

Drew mostly lived up to his first-round billing with a long, solid career. Unfortunately, the only benefit he ever provided to the city of Philadelphia was the increase in battery sales.

Before the 1997 draft, Drew’s agent Scott Boras warned the Phillies not to draft him. It isn’t clear if Drew didn’t want to play in Philadelphia or Boras didn’t think the team would meet his contract demands. Whatever the reason truly was, the Phillies didn’t listen and drafted him anyway.

Boras may be a weasel, but he wasn’t lying about Drew being difficult to sign. There were long drawn-out negotiations that eventually resulted in Drew returning to the draft. He was drafted by the Cardinals (who almost immediately gave in to Boras’ demands) and the Phillies were awarded a compensatory pick.

While most of the blame clearly lies with Boras, if the Phillies weren’t going to eventually be willing to give in to his demands, then they never should have drafted him.

1. Jeff Jackson

Pictured: Not jeff Jackson. Image Credit: Dennis Wierzbicki-USA TODAY Sports

Positives about Jeff Jackson: He had a pretty sweet high top fade hairstyle.

Negatives about Jeff Jackson: Never played a game in the major leagues, the team passed up Frank Thomas to draft him.

Yes, not only did the #4 overall pick in the draft not reach the major leagues, to draft him, the Phillies passed up guy who was just voted into the Hall of Fame. Oops.

Jackson had speed, but that’s about all he ever displayed. He couldn’t get on base, and he couldn’t hit for any power. That’s generally a bad combination for a potential major league baseball player.

Tags: Mlb Draft Philadelphia Phillies

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