MLB Writer Opines Dodgers Biggest Free Agent Regret

Despite former Dodgers All-Star Yasmani Grandal inking a multi-year contract with the Chicago White Sox on Thursday, we’re saddled in that weird Hot Stove lull before the Winter Meetings. Now is when news is a bit tougher to come by, so you find your fun in editorials and opinion pieces.

Over at MLB.com, columnist Will Leitch editorialized a topic that surely sparks debate among the 30 fan bases — “every team’s biggest free agent regret.

Moreover, Leitch opines that Darren Dreifort’s five year, $55M deal was the most regrettable free agent contract in Dodgers history.

Here’s the full section:

Dreifort pitched only 200 innings after Los Angeles gave him this deal, and he retired at the end of it.

That’s it.

Understandably, it can be difficult to come up with 30 different free agent flops for each team — especially for teams that you may not have in-depth knowledge on.

But I’m going to respectfully disagree with Mr. Leitch here, and open this up to debate amongst Dodgers Nation.

I’ll start with my first retort to the source material.

Argument One

Darren Dreifort was the Dodgers’ first pick in the 1993 first-year player draft — he was the second overall pick behind none other than Alex Rodiguez. Dreifort made his Major League debut with the club in 1994 before ever playing a minor league game.

The right-hander pitched with Los Angeles from 1994-1999 before becoming a free agent. In the 1999-2000 off-season, the Dodgers and Dreifort agreed to that aforementioned five-year deal and he played through a number of injury issues before retiring at the end of his contract in 2004.

Now, this is where we reach the grey area that, depending on how you view it, could blow up the entire setup for the MLB.com article:

Should Darren Dreifort be considered a true free agent signing for Los Angeles?

Yes, technically the former pitcher’s transactions page will read “December 11, 2000: Signed as a Free Agent with the Los Angeles Dodgers,” but considering he re-signed with his former club, do you consider him a free agent for the sake of the article’s argument?

Nevertheless, we’ll play along and next argue against Dreifort as the biggest free agent regret for the Dodgers.

Argument Two

As Leitch mentioned, Dreifort only tossed 200 innings over the life of the contract, thanks in part to Tommy John surgery that cost him most of 2001, and all of the 2002 season.

In Dreifort’s final season, he played a key role out of the bullpen for Jim Tracy’s Dodgers. He appeared in 60 games and pitched to a 3.98 FIP acting as a bridge for Guillermo Mota and reigning Cy Young closer Eric Gagne.

His knee ultimately gave out during the stretch run of the ’04 season, but he was instrumental in helping the Dodgers reach their first postseason in eight years.

When healthy, Dreifort was a nasty dude… (shout out to a baby David Ross).

Taking the long way to get here, while the contract is undoubtedly not pretty, it is hardly a complete albatross (this is purely my opinion of course). And when you consider some other names in recent history alone, you wonder why the MLB author chose Darren Dreifort out of obscurity.

Better Recent Options

  • Andruw Jones – 2 years, $36.2M
    • Jones hit to the tune of a 38 (!) wRC+ over 75 games and just one season before being released (ousted) by Los Angeles in the off-season. Worst of all, the Dodgers paid for the failed signing through the 2014 season… five years after he was released. (Woo! Deferred payments!)
  • Jason Schmidt – 3 years, $47M
    • When the Dodgers signed Schmidt, his shoulder was being held together by bubblegum and hopeful thoughts. LA GM Ned Colletti knew this was the case having just worked together with the Giants organization as recently as two years prior. Nevertheless, Ned offered up one of his famous 3-year contracts and the Dodgers got a total of 43.1 innings pitched and 5.37 FIP out of Schmidt over the life of it.

Legacy Option

If we’re looking to go back even further for the sake of flexing our memory banks of useless knowledge, people can cite the five-year deal inked by Darryl Strawberry that netted the Dodgers only 214 games played before being released ahead of the fourth year.

Final Thoughts

As writers, we’re all entitled to our opinions, but sometimes our opinions are wrong. All joking aside, it’s safe to say that at the very least Will Leitch was very successful in stoking conversation…

Who is your biggest free agent flop for the Dodgers? Let us know in the comments below.

Clint Pasillas

Clint Pasillas has been writing, blogging, and podcasting about the Los Angeles Dodgers since 2008. Under Clint's leadership as the Lead Editor, Dodgers Nation has grown into one of the most read baseball sites in the world with millions of unique visitors per month. Find him online on Twitter/X or his YouTube channel!


  1. Wow! you are so right. I when I initially saw the article (without reading it), I immediately thought of both Jones and Schmidt. Both of those signings were abhorrent to the Dodgers during their time.

    The Dreifort signing did not register at all. I loved Dreifort during his tenure in LA. I just wished the Dodgers would have played him more on the field. Guy could mash. Came out of college as a two way player. Dodgers should have explored that a little more.

  2. Too bad Dreifort couldn’t have been converted to a first baseman. He stroked some nice home runs for the Dodgers as a pitcher (6 in five years) but in College in 1993 he was the DH for the Wichita State Shockers and knocked 22 home runs which was second to the team high of 28. He was a 3 time All Missouri Valley Conference player as a pitcher and Designated Hitter-Utility Player. But I guess when the Knee goes, its goes… In those days there wasn’t a lot you could do about it. Surgery is so much more advanced and automation assisted that the surgeries are more precise with out as much time needed for healing as back then… I those days, there was a lot of cutting with scalpels that left little room for error….

    It was too big of contract for the times, worked out by Scott borA$$ on the basis of future potential, not consistent accomplishment…

  3. What a botch job on him. Called up with no minor league experience? No wonder he was always a hack

  4. Clint, I very much agree with you and the other two who have responded here. I would rate Strawberry as the worst, for a Dodger career of awesumly Bad, Jones 2nd, then Schmidt. In one game, Jones, my no. 2, K-ed FOUR times and GIDP in one of his 5 ABs. i hate $$$ FAs.

  5. That YouTube video pretty much said it all about Darren Dreifort. David Ross couldn’t catch Dreifort’s slider/sinker, neither could Mike Piazza. It wasn’t until Charles Johnson became the catcher that Dreifort began to flourish. He could throw any type of pitch to Charles Johnson. Dreifort was awesome from 1999 – 2000.

    1. 13-13 with a 4.79 in 1999
      12-9 with a 4.16 in 2000
      He had good stuff for sure but his problem was he was done a disservice having had very little time in the minors to fully develop. When not injured he was just an average pitcher with moments of filthy stuff

    1. But they were at least, “forgettable” along with being “regrettable”. A few of us here will never “forget” Strawberry, Jones, and Schmidt. Give me 5 ABs, and I can strike out 4 times and IF the opportunity presents itself, GIDP. Looking at you, Andruw Jones.

  6. I’d have to go with Darryl Strawberry. Much hyped homecoming that fell flat. He couldn’t keep his nose clean.

    1. In general, I absolutely hate signing mercenaries from another team. Put them in a Dodgers uniform and watch them under-perform. Maybe it’s the movee starz, maybe it’s the Golden-ness of the state of California. Maybe it’s the sky-high taxes of CA. Don’t know but it always UNDERWHELMS in my humble opinion. The Bats won WITHOUT Harper.

  7. Darren Dreifort was a sad case. He appeared to have the potential to be Drysdale reincarnated, even the name had that ring. He had one injury after another. My perception, however, was he was hell bent to try to earn his money. He retired only after multiple attempts to contribute. Flashes of what might have been, but a tragic career overall. He was worth the signing risk. Jones and Schmidt were far worse.

  8. I’m a Dodgers fan to the end. I have followed them from a boy. I am now three score ten.

Leave a Reply

Your email address will not be published. Required fields are marked *

Back to top button