The 10 best draft picks gained by losing a free agent

Dilip Vishwanat

Think about what the Marlins got for Miguel Cabrera, who was 25 and the best hitter in baseball when he was dealt. It wasn't a lot. The only thing the Marlins have to show for Cabrera right now is Ryan Webb. That trade chain was like the evolution timeline taking us from mighty archaeopteryxes to filthy pigeons.

Now think about what the Red Sox got for Pedro Martinez. And what the Cardinals got for Albert Pujols. They each got someone who pitched in the League Division series on Monday. Clay Buchholz was the compensation pick for Martinez, and Michael Wacha was the compensation pick for Pujols. They weren't trades. But if they were, we'd think of them as brilliantly executed trades. A superstar on the other side of the hill for a prospect with superstar potential? You take that almost every time.

Compensatory draft picks aren't a new thing. They've been around since 1977, when the Yankees drafted Rex Hudler with the pick they got from the White Sox for losing Ron Blomberg. Wacha's success made me curious about the greatest compensatory draft picks in history. Wacha isn't going to be on there. Yet. But this list will probably be a lot different in a few years. You never know when Sherard Clinkscales is going to make a comeback.

10. Jacoby Ellsbury (Red Sox-1) - Pick from Angels as compensation for Orlando Cabrera
Clay Buchholz (Red Sox-1s) - Supplemental Pick for loss of Pedro Martinez
There are players who would have been on this list if it were a straight WAR ranking, like Travis Fryman and Brian Jordan. But there's a symmetry with these two that's impossible to ignore. Cabrera and Martinez were huge parts of the 2004 team, but both were allowed to leave via free agency. Which seems hard to believe in retrospect.

Somehow they magically transmogrified into the best players on this year's playoff team. Both of them were also positive contributors to the 2007 World Series team -- probably the difference between AL East champs and the Wild Card. That's an amazing return for Martinez and Cabrera if you look at it like a trade.

9. Shawn Green (Blue Jays-1) - Pick from Giants as compensation for Bud Black
Now, the problem with this exercise is that you can't just assume that the team losing the pick would have chosen the same player.

Just know that if Green had gone to the Giants, he would have been sucked into the ethereal void of outfield prospects that has sucked in every Giants outfield prospect since Chili Davis. The list of homegrown outfielders, since Davis debuted in 1981, ranked by WAR:

1. Marvin Benard
2. Dan Gladden
3. Mike Aldrete
4. Darren Lewis
5. Armando Rios
6. Fred Lewis
7. Nate Schierholtz
8. Calvin Murray
9. Randy Kutcher
10. Juan Perez

Green would have been ruined. Also, Perez would have finished sixth in MVP voting this year if he were drafted by the Cardinals.

8. Wally Joyner (Angels-3) - Pick from Yankees as compensation for Don Baylor
If I had taken the money I spent on Joyner rookie cards and bought Apple stock instead, I would be closer to a millionaire. I can't figure out the exact numbers, but I had about $200 worth of Joyner cards in 1987.

But it's worth remembering that Joyner had a long, productive career, even if he didn't make you rich. It wouldn't hurt to ask him for money if you see him, too. Same thing applies with Hensley Meulens. And Eric Anthony.

7. Mark Gubicza (Royals-2) - Pick from Cardinals as compensation for Darrell Porter
His career stats don't look super-impressive, but he gets bonus points for sticking with the team that drafted him for almost his entire career, and for winning a World Series four years after being drafted. If you're going to lose a guy like Porter, who was one of the more underrated players of his generation, at least you can get a championship and a dozen years out of the consolation prize.

6. Torii Hunter (Twins-1) - Pick from Reds as compensation for John Smiley
Smiley pitched only one season for the Twins. It was a good season, but the price was steep -- they gave up Denny Neagle, who became one of the better Pirates pitchers over the past two decades. And they exchanged Neagle for Jason Schmidt, who was also one of the better Pirates pitchers over that span.

But if you're going to give that up, give it up for a franchise center fielder. The Twins then got two picks for Hunter going to the Angels, but neither of them panned out.

5. Mark Langston (Mariners-2) - Pick from Rangers as compensation for Bill Stein
And if we're going to play the trade-chain game, not only did Langston have a fantastic career with the Mariners, but he was traded for Randy Johnson, who in turn led to Freddy Garcia and Carlos Guillen, who were huge parts of the 116-win season in 2001.

Basically, half of everything good that has ever happened to the Mariners in franchise history happened because someone on the Rangers really, really wanted Bill Stein, who was the Ryan Theriot of his day.

4. Mike Trout (Angels-1) - Pick from Yankees as compensation for Mark Teixeira
And here we learn of Mark Teixeira, franchise builder. He is the Reverse Galactus of the AL West, making life where none existed before. He's tangentially responsible for the Rangers' two pennants, and he's the reason the Angels have the best player in baseball for at least the next four seasons.

Now picture Trout on the Yankees.

But the Yankees used Teixeira to win a World Series, too, so it's one of those win-win things. Except that the rest of the world who had to watch the Yankees win it. Mostly win-win, though.

3. David Wright (Mets-1s) - Supplemental Pick for loss of Mike Hampton
Hampton was just as good of a hitter, but he couldn't field third worth a lick. The Mets came out ahead on that one. While there are a lot of impressive names on this list, there aren't a lot of Hall of Famers. Wright's probably about three or four good seasons away (or six/seven decent years for the counting stats). Depending on what Trout does, Wright has a good chance to retire as the greatest supplemental pick of all time.

2. Johnny Damon (Royals-1s) - Supplemental Pick for loss of Kurt Stillwell
Stillwell was the big prize the Royals got for trading 25-year-old Danny Jackson, but the shortstop was kinda sorta okay, nothing more.

But thinking about Damon and the Royals depresses me. Mark Ellis went with Damon to the A's, meaning that close to 100 wins went the other way in a trade that brought back Angel Berroa and A.J. Hinch.

Even worse is the idea that Hinch as a manager or general manager probably would have led to more Royals wins. Not like Hinch has proven himself in either capacity … but you're quietly nodding your head.

1. Rafael Palmeiro (Cubs-1) - Pick from Padres as compensation for Tim Stoddard
This would have been the only Hall of Famer on the list, if not for the unpleasantness that followed. And that's also one of the Padresiest things I've ever typed. The Padres have a rich history of talent slipping through their fingers -- from Ozzie Smith to Gary Sheffield to Roberto Alomar. Of course they have the #1 player on this list.

Here's Tim Stoddard. He was, like, the Hector Carrasco or Guillermo Mota of his day. But he apparently impressed the Padres during the 1984 NLCS, and that's the story of how they lost the chance to draft and sign Rafael Pameiro.

Of course, the Cubs wasted him, too. Maybe that was the worse fate after all.

In the team photo:

Todd Zeile (Cardinals-2s) - Supplemental Pick for loss of Ivan de Jesus
Travis Fryman (Tigers-1s) - Supplemental Pick for loss of Lance Parrish
Brian Jordan (Cardinals-1s) - Supplemental Pick for loss of Jack Clark
Rondell White (Expos-1) - Pick from Angels as compensation for Mark Langston
Chris Carpenter (Blue Jays-1) - Pick from Rangers as compensation for Tom Henke
Brian Roberts (Orioles-1s) - Supplemental Pick for loss of Rafael Palmeiro
Adam Wainwright (Braves-1) - Pick from Diamondbacks as compensation for Russ Springer
Nick Swisher (Athletics-1) - Pick from Red Sox as compensation for Free Agent Johnny Damon
Gio Gonzalez (White Sox-1s) - Supplemental Pick for loss of Tom Gordon

Worth nothing: Zach Cone was a supplemental pick for the Angels because they couldn't sign Matt Harvey. Whoops.

More from Baseball Nation:

Sympathy for C.B. Bucknor

Predicting the AL playoffs

Predicting the NL playoffs

Clayton Kershaw’s big test

Jim Bouton on the ‘63 World Series

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