When general managers went bad

June, 3, 2014
Jun 3
7:34
PM ET
There are a million stories about the Major League Baseball amateur draft, or the First-Year Player Draft as it's officially called (thank you, J.D. Drew and Scott Boras). Here are some of the biggest ones during the draft's 50-year history, courtesy of Allan Simpson, the founder of Baseball America.

One interesting aspect of the draft has been the history of compensation picks. These are the picks teams surrender when they sign a top free agent. The rules have changed through the years, but beginning in 1978, the general rule was if you lost a Type A free agent you received the signing team's first-round pick if it was in the bottom half of the draft or the team's second-round pick if it it was in the first half of the round. There were also supplemental picks between rounds that would be applied.

The rules are slightly different now, but we saw how much teams value draft picks when free agents like Stephen Drew and Kendrys Morales were left unsigned or Nelson Cruz had to settle for a one-year deal. Those players were tied to draft picks, so a team drafting 11 through 30 would have lost its first-round pick for signing them (along with the slot money allocated for that draft position).

But teams haven't always valued draft picks so highly. I thought it would be fun to go through and check the worst free agent signings that cost a team a first-round pick. It's pretty amazing how dumb general managers used to be.

WORST FREE AGENTS: THE EARLY YEARS

The first years of free agency led to some of the worst free agents signings. Yes, free agency was new and maybe general managers didn't fully understand the system, but it also shows how clueless many front offices were back then and how they failed to properly evaluate the value of players. Yes, first-round picks -- especially late in the round -- rarely develop into stars, but there's always that chance one will turn into one, and signing a scrub just isn't worth it. But consider some of these signings:

1. Ron Blomberg, White Sox, 1978. The first-ever compensation pick was Rex Hudler, taken 17th overall by the Yankees for losing Blomberg. You may remember Blomberg as the first designated hitter but when the White Sox signed him he had played one game in two years due to shoulder and knee injuries. He played 61 games for the White Sox before retiring. Hudler only played a few games with the Yankees but did have a long career as a utility player.

2. Rowland Office, Expos, 1980. Office had hit .246 with 16 home runs over the previous three seasons as a part-time player with the Braves, worth -3.2 WAR. Yes, minus. He played OK for the Expos in 1980 but lasted just 31 more games in the big leagues. Ex-teammate John Milner would testify during the Pittsburgh drug trials in 1985 that he used cocaine during games with Office. Braves selected: P Jim Acker (5.8 career WAR).

3. Dave Roberts, Astros, 1981. When signed, Roberts hadn't batted more than 251 times since 1974. He'd hit .238 with 10 home runs as a utility player for the Rangers in 1980. The Astros, coming off a loss in the 1980 NLCS, apparently thought he could put the team over the top. He didn't. Roberts had 59 plate appearances in his Astros career. Rangers selected: P Al Lachowicz (0.2 WAR).

4. Larry Biittner, Reds, 1981. Two i's, two t's. Biittner was a platoon first baseman/corner outfielder coming off a year where he'd hit .249 with one home run. He was 35 years old. Yes, general managers used to think this type of players had value or had veteran presence. Or something. Biittner played sparingly in two years with the Reds and was released. Cubs selected: P Vance Lovelace (0.0 WAR).

5. Tim Blackwell, Expos, 1982. Not learning from the Office mistake, the Expos decided they needed a 29-year-old backup catcher with six career home runs. Blackwell played 29 games for Montreal. Cubs selected: SS Tony Woods (never reached majors).

6. Pete Falcone, Braves, 1983. Falcone was a 29-year-old lefty coming off a decent year with the Mets (3.84 ERA), so this wasn't quite as bad as the others. But it's worth mentioning because with a supplemental pick received for losing Falcone, the Mets drafted Calvin Schiraldi ... whom they later traded to the Red Sox and, well, you know the rest. Mets selected: OF Stan Jefferson (-0.2 WAR).

THE MID-'80s TO MID-'90s
In this period, teams started wising up, at least a little bit. But there were still some bad players teams were willing to punt their first-round pick for.

1. Tim Stoddard, Padres, 1985. To be fair, the former NC State basketball player did have a good year as a reliever with the Cubs in 1984 with a 3.82 ERA in 92 innings. But he'd also had a 6.09 ERA the year before and always had trouble throwing strikes. Stoddard lasted just over a year in San Diego before he was traded for Ed Whitson (which actually turned out to be a good trade). But the Cubs got a pretty good compensation pick. Cubs selected: OF Rafael Palmeiro (71.6 WAR).

2. Rick Dempsey, Indians, 1987. Dempsey was a 37-year part-time catcher with great defense and no bat. GM Joe Klein decided he needed to have a .208-hitting catcher. Hey, this was the year Sports Illustrated picked the Indians to win the World Series. Dempsey hit .177, was released, the Indians lost 101 games and Klein was fired. Orioles selected: P Brad Duvall (never reached majors). They also get P Pete Harnisch as a supplemental pick.

3. Eddie Milner, Reds, 1988. Milner had hit .259 with 15 home runs in 1986 for the Reds and was then traded to the Giants, where he was bad in 1987. The Reds decided they needed him back, even though he was 33 years old and they had Eric Davis, Kal Daniels and Paul O'Neill in the outfield. He played 23 games and his career was over. Giants selected: SS Royce Clayton (19.5 WAR).

4. Ken Oberkfell, Astros, 1990. Oberkfell had once been a decent player but by 1990 was a 34-year-old backup infielder who hadn't posted an above-average OPS since 1984. This would kind of be like signing Willie Bloomquist and giving up your first-round pick. Except Oberkfell couldn't even play shortstop. Oberkfell hit .214 with one home run in two seasons. Giants selected: OF Adam Hyzdu (-0.1 WAR).

5. Ken Dayley, Blue Jays, 1991. Dayley was a 32-year-old lefty reliever and had a string of good seasons with the Cardinals, but he immediately got hurt and pitched just five innings with the Blue Jays. By the way, the Toronto GM was Pat Gillick. More on him later. Cardinals selected: P Allen Watson (2.8 WAR).

6. Damon Berryhill, Reds, 1995. When signed, he was a 31-year-old catcher with a career OPS+ of 77. He hit .183 for the Reds and was released the following spring. Red Sox selected: OF Corey Jenkins (never reached majors).

THE MODERN ERA

OK, general managers had gotten a lot smarter. More of them knew about sabermetrics. Or, maybe more importantly, as salaries increased, front offices simply started valuing young (ie: cheap) players more. But there were still questionable signings, mostly relief pitchers ...

1. Doug Henry, Astros, 1998. Henry had posted a 4.78 ERA over the previous two seasons and was 34 years old. He actually helped the Astros to the postseason in '98 by going 8-2 with a 3.04 ERA. Still. Giants selected: OF Tony Torcato (-0.1 WAR). OK, you've noticed that a lot of these picks never panned out. But the player drafted after Torcato was CC Sabathia, so the Astros lost a chance at drafting Sabathia by signing Henry.

2. Mike Magnante, A's, 2000. Another reliever. He'd posted a 3.38 ERA for the Angels in 1999 and pitching was scarce in those steroid-infused days of yore, but he also owned a 4.10 career ERA and was 35. Angels selected: P Chris Bootcheck (-1.5 WAR). But Adam Wainwright went later in the round.

3. Sandy Alomar Jr., White Sox, 2001. A good player in his prime but at this point he was a 35-year-old catcher coming off two injury-marred seasons. Indians selected: P Alan Horne (never reached majors).

THE PAT GILLICK MEMORIAL GROUP
Gillick -- that's Hall of Famer Pat Gillick -- was the Mariners' general manager from 2000 through 2003 and then a special consultant for Seattle in 2004 and 2005. During this era he helped build four straight 90-win teams plus the 116-win team of 2001 (although he obviously inherited a good deal of talent as well). Gillick was a win-now GM but his decisions to sign many free agents over multiple years also created a valuable lesson. A quick look:

2000 -- Lost first three picks for signing John Olerud (good), Aaron Sele (good) and Arthur Rhodes (good, except for those pitches to David Justice). Also signed Mark McLemore, who didn't cost the Mariners a pick.

2001 -- Lost first-round pick for signing Jeff Nelson (did have one good season and made the All-Star team in 2001).

2002 -- Failed to sign first-round pick John Mayberry Jr.

2003 -- Lost first-round pick for Greg Colbrunn. This made no sense. First, the Mariners still had Olerud and Edgar Martinez to play first base and DH. Colbrunn had been a part-time player for the previous six years and was 33. Why give up first-round pick? He'd play 22 games for Seattle and was traded back to Arizona after the season.

2004 -- Lost first-round pick for Eddie Guardado (the Twins drafted Glen Perkins with the pick). They also lost their second-round pick for signing Raul Ibanez (although he had some good years as the rest of the team fell apart).

2005 -- Lost second- and third-round picks for Adrian Beltre and Richie Sexson.

Anyway, other than Colbrunn, none of the free agents were disasters, but in the big picture all those signings cost the Mariners a lot of early picks and the farm system dried up for a five-year span. Those missing years helped create the losing seasons in recent years. Mix in some bad trades under Bill Bavasi (Adam Jones, Shin-Soo Choo) and Gillick's win-now strategy, while successful for a few years, also hurt the Mariners in the long run.

BEST COMPENSATION PICKS
Here's a list of the 10 best compensation picks. I looked only at first-round selections and didn't include supplemental picks. There have been some good players selected that way -- David Wright, as one example, was a supplemental pick the Mets received for losing Mike Hampton.

1. Mike Trout, Angels, 2009 (25th overall). From Yankees for losing Mark Teixeira.
2. Rafael Palmeiro, Cubs, 1985 (22nd). From Padres for losing Tim Stoddard.
3. Torii Hunter, Twins, 1993 (20th). From Reds for losing John Smiley.
4. Chris Carpenter, Blue Jays, 1993 (15th). From Rangers for losing Tom Henke.
5. Adam Wainwright, Braves, 2000 (29th). From Diamondbacks for losing Russ Springer.
6. Jacoby Ellsbury, Red Sox, 2005 (23rd). From Angels for losing Orlando Cabrera.
7. Shawn Green, Blue Jays, 1991 (16th). From Giants for losing Bud Black.
8. Michael Wacha, Cardinals, 2012 (19th). From Angels for losing Albert Pujols.
9. Charles Nagy, Indians, 1988 (17th). From Giants for losing Brett Butler.
10. Nick Swisher, A's, 2002 (16th). From Red Sox for losing Johnny Damon.

David Schoenfield | email

SweetSpot blogger

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