If I could go back in time to undo a deal, I’d rather undo the Pujols contract than Vaughn. It was less destructive to the team because it was shorter.

It didn’t even turn out all that bad. 2 productive years, one year missed to injury, and they were able to trade him for a guy who helped the team win the only WS in franchise history.

I’d also nominate Chris Davis. He didn’t change teams, but he did make it to the free agent market and was able to field offers from other teams before resigning with the Orioles.

Kei Igawa cost the Yankees 46 million bucks for 5 years.
The yankees got 2 wins and a 6.66 era for their investment.

The Marlins made out perfectly fine on the Jose Reyes signing. He also performed well with the Blue Jays after they traded him. Then the Jays traded him to the Rockies for Tulowitzki. In hindsight that didn't work out very well for the Rockies, but it wasn't a disaster in terms of production. Tulo was only so-so for the Jays. I don't I don't see how you can say Jose Reyes was a bad free agent signing.

Yeah, Marlins made out well. They had Reyes on a backloaded contract, paid him 10 million for one year, a 3 WAR season. Then offloaded the contract and got assets in return.

Even if you look at the whole deal, Reyes was paid for 6 years and gave his teams only 3 good ones. Probably better than the Angels signing Zack Cozart for 3 years and getting nothing out of it.

Cristian Guzman and Julio Lugo (both given honorable mention at shortstop) don't strike me as god awful either (well, maybe Lugo), so there may not be very many bad shortstop FA deals. Maybe Hanley Ramirez, but he didn't really play SS in Boston.

I thought for sure Ellsbury would have represented the Yankees here... (I had completely forgotten Pavano's stint with the team)

Wouldn’t the worst re-signed list be much worse? Maybe Ryan Howard is just casting a fat shadow, but these outside signings mostly don’t seem all that bad

Yes, there need to be two categories: "least value for the money as it turned out," but also "we could have told you that was a disaster from the start."

Mo Vaughn was just shy of 31, an established star, went on to hit 69 HR in the next two years, then got hurt (as Rally notes).

Gary Matthews Jr., now, had a career OPS+ of 97, and at age 32 was coming off by far his best season ever. The odds of him staying that good for five years or even one year were basically nil. (TFA does give the Matthews contract honorable mention.)

Josh Hamilton, signed at age 31, is somewhere in between. Some people at the time thought the Angels had done great – Hamilton like Vaughn was a legitimate star. But he had visibly lost a step (or more) in the outfield and a huge 5-year deal was clearly not advisable. Still, I thought he would do OK for a year or two in Anaheim …

For all their MoneyBall savvy, and given their self-imposed limited budget, the A's have turned in some real stinkers in recent years. Off the top of my head.

Khris Davis, 3 years, $16.5 million per, for nothing (though it's possible that their swap for Elvis Andrus may turn out ok)
Billy Butler, 3 years, $10 million per, for nothing
Trevor Rosenthal, 1 year, $11 million, for nothing

Mo Vaughn

Gary Matthews Jr.,

Josh Hamilton,

Gee the Angels have not covered themselves in glory over the years....

Angels have not covered themselves in glory

And trading Mike Napoli for Vernon Wells isn't even in this discussion :)

The cardinals get two honorable mentions with Tino and Dexter - well earned. Brett Cecil should have gotten and honorable mention on relief pitchers.

The cardinals have been repeatedly saved by fate. They almost signed Pujols, Heyward, Price and nearly bought Stanton’s big contract. Instead they got Holliday, Goldschmidt and Arenado. Jury is still out on Arenado but if that isn’t devil magic , I don’t know what is.

#9: Technically Khris Davis wasn't a FA signing.

Agreed I don't see any reason to limit this to FA signings. A long-term extension for a player (esp if they have 6+ service time or are over 30) is the same thing.

Todd Hundley seems a bit unfair. As the article notes, in 1998, Vaughn got 6/$80 and Albert got 5/$65 and, in 2000, Hampton got 8/$120. Hundely is cited here for 4/$23.5 in 2000 ... not chump change but hardly an expensive contract even in those days. He had been obviously terrible in 98 and not good in 99 and only made 82 starts in his excellent 2000 so the Cubs knew they weren't getting a star and didn't pay him star money.

Granted, there haven't been a lot of C FA contracts and most seem to have worked out OK so maybe it was just a lack of competition. It is hard to beat a zero in the denominator of a $/WAR calculation after all. B McCann 5/$85 for 7.5 WAR; Martin about the same; Pudge worked out very well for Detroit. Those are the ones that spring to mind. James McCann might give Todd a run for his money.

And trading Mike Napoli for Vernon Wells isn't even in this discussion :)

And the Justin Upton trade (and short extension) hasn't worked out too well either. CJ Wilson was better than I remember but nothing to brag about.

And while it pales in comparison to Napoli for Wells, why does nobody ever give the Jays grief over Napoli for Frank Francisco 4 days later?

#14 The Jays did get a lot of grief for Napoli. I mean he was a monster in 2011 and when you've moved an all-star for a generic middle reliever people are going to remind you.

But here's the thing. They'd have cheerfully moved Wells for a month old bagel. Getting a year of reasonable middle relief was way more than they'd hoped for and everybody knew it. It's hard to be too critical.

Tulo was only so-so for the Jays.

The Jays got 5 WAR over 2.5 seasons from him, but were still paying him 3+ seasons after he played his last game for them. All told, they ended up on the hook for roughly $100 million for that performance, so so-so might be overstating things a little.

Madison Bumgarner is making a bid to join this list

5 years 85 M. Through first two years with Dbacks

35 GS, 188 IP, 5.07 ERA, 5.20 FIP, 1.1 WAR, 37 HR allowed ! Struggles to break 90 on his FB, cutter sits in low to mid 80’s at best. It’s a miracle his numbers aren’t worse

MadBum just needs to discover his inner Moyer.

The Dodgers had a couple of "great" free agent signings in the first years of of free-agency in 1980

Dave Goltz, 6 years, $3 million, -0.5 WAR and then released
Don Stanhouse, 5 years, $2.1 million, -0.7 WAR

These two washouts didn't stop them from winnning a World Series in 1981, of course.

19. Then LA signed Rick Honeycutt. When he started off roughly, the fans dubbed him "Honeygoltz"

Honeycutt came over in a trade with the Rangers for Dave Stewart and a PTBNL, replacing Burt Hooton in the rotation in 1984, who was demoted to the Bullpen. Hooton himself then went over to the Rangers in 1985 but was really done by that point. Honeycutt later got traded to the A's for Tim Belcher, joining Dave Stewart, then the Dodgers beat the A's, who also had acquired Bob Welch, and who had let Mike Davis leave as a free agent to join the Dodgers. Mike Davis had a terrible season for the Dodgers in 1988, only to pinch hit in the first game of the World Series, and coax a walk which allowed Gibson an at bat, where of course he hit his famous home run. Also in the strange Texas/Oakland/Dodger continuum that year was Jay Howell, who came over from the A's just the year before in the trade that sent Bob Welch to the A's, which also brought Alfredo Griffin from the A's and Jesse Orosco from the Met's to the Dodgers.

Rather than putting up the pre-inflated numbers of old busts it would have been worth listing % of payroll. Of course that might make bad NYY signings look better but a bust might hurt the Royals more than the Dodgers if the teams were otherwise competitive. That's probably what the writer is thinking in putting in Mark Davis.

1B really seems like the position with lots of groaners. Mo, Pujols, Hosmer, Davis, Fielder plus early extensions for Miggy and Howard ... could add in the Glenn Davis trade and FA/extension, maybe even the Richie Sexson trade. FOs always dig power of course so it makes sense that the biggest contracts mainly go to 1B/OF (and young power-hitting SS) so that's where we'd expect to find the most spectacular flops but that still seems like a pretty long list and my memory of 70s-90s FA deals isn't that good -- Glenn Davis got about $10 M out of the O's for 3 year which doesn't sound like much but, at the time, that was the highest AAV in O's history.

MadBum just needs to discover his inner Moyer.

He's tried. I got to speak with him multiple times between ST and end of the season. I was especially interested to see if and how he was developing his Changeup which he had previously used sparingly.

He said that he was trying but it was simply a pitch he has never had a feel for and it was his 4th best pitch, so he didn't try to throw it much. But he started trying to use it more last year and by August-September he threw many more than usual, but he didn't get good results

Without the ability to dial in the Changeup, I don't see how he's going to be able to have a Moyer like old age. His Fourseam/Cutter/Curverball repertoire just isn't cutting it anymore. (Pun not intended)

Rather than putting up the pre-inflated numbers of old busts it would have been worth listing % of payroll. Of course that might make bad NYY signings look better but a bust might hurt the Royals more than the Dodgers if the teams were otherwise competitive. That's probably what the writer is thinking in putting in Mark Davis.

Maybe percent above league average salary but that's a lot of work.

I don't agree with naming Albert Belle as the worst FA OF signing ever.
For six years in a row, 93-98 he's in the conversation for best hitter in baseball not named Bonds, averaging 160 OPS+.
Coming off a 7.1 bWAR 172 OPS+ season, he opts out of his contract with CWS, and Baltimore signs him for 5 years.
He produces a 143 OPS+ season, then gets hurt. He limps through 2000, then never suits up again. They keep him on the 40 man roster, so insurance covers most of the salary, thus they are not financially hamstrung.

Guy got hurt, what can you do? He was a great hitter, and had earned a big paycheck. (Unless "degenerative hip condition" is just a euphemism for something else?) Give him the MVP he deserved in 1995 instead of Mo Vaughn, and he was on a Hall of Fame trajectory. And maybe Vaughn is not on this list, because he doesn't get overpaid so much after being overrated.

Speaking of Vaughn, I'd consider Greg Vaughn for this list before Belle. Article doesn't mention him: signed by Tampa Bay 4/$34M in 2000 (star-level money) he put up OPS+ of 119, 103, 62, then released in spring training. So TB had to pay him out, right? That's a bad return on investment. I suspect that's now a gold standard bad contract, mixing in that Greg was 34 when he signed it.

ed: signing GVaughn for big money was perhaps not as rare for TB as I remembered. They were just bad, I forgot who the players were, but in that era they were also throwing big money (not always as FA signings, just in terms of bad $$$) at vets like Vinny Castilla, Wilson Alvarez, and Roberto Hernandez that weren't giving them much production.

He said that he was trying but it was simply a pitch he has never had a feel for and it was his 4th best pitch

There are so many changeup grips. I hope he is using the offseason to find a changeup that works. He seems like a bright guy, Brent Strom, the new Diamondbacks pitching coach, coached Dallas Keuchel, a noted changeup artist. I betcha there are quite a few former major leaguers with good changeups living in Arizona that could help as well. Alas, Doug Jones is no longer one of them.

He's tried.

It took Jamie himself about 15 years, MadBum just needs to be patient. :-)

#26: the brand new Devil Rays were trying to make a quick splash. Looking back, in year 1, they already had McGriff, Boggs, Alvarez, Arrojo (the big pitching prize out of Cuba), Hernandez and several other recognizable vet names. Alvarez by the way had been a very good pitcher and was pretty good for the Rays in his first two seasons then got hurt. That didn't work well in 98-99 so ... they decided to try again with Castilla and Vaughn in 2000. That first wave of signings worked out pretty well -- McGriff, Alvarez (until hurt), Arrojo and Hernandez all produced, Boggs was just there to sell tix and try to steal a HoF plaque. The second wave not so good. Oh well, at least they tried.

#23, likely due to old player skills and the early aging thing.

they decided to try again with Castilla and Vaughn in 2000.

That haul also included Juan Guzman, who got $12 million over two years for 1.2 IP.

Darren Dreifort was a Dodger doozy. Don't the Red Sox have a minor league fiasco out of Cuba they paid $50M for?

I used to love to keep track of Steinbrenner's lousy moves, going as far back as the Steve Kemp & Dave Collins moves.

Merry Christmas all.

I forgot about Yasmany Tomas

4 years 68 Million

309 Games, 1175 PA, -2.5 WAR, -6.2 WAA

DFA’d and Banished to AAA in 2018, saw all of 6 more PA in MLB after that

Wow, I didn't know about Yasmany Tomas.

At least Arizona got one year with 31 home runs from him. The Yankees didn't even get that from Kei Igawa.

Rather than putting up the pre-inflated numbers of old busts it would have been worth listing % of payroll. Of course that might make bad NYY signings look better but a bust might hurt the Royals more than the Dodgers if the teams were otherwise competitive. That's probably what the writer is thinking in putting in Mark Davis.

The Royals had the highest payroll in baseball when they signed Mark Davis.

Two words: Wayne Garland. After that experience, the Indians forsake the entire notion of pursuing a big name free agent.

Cleveland later masterminded the practice of extending young stars early though ... which is what they were trying to do by signing Garland. (If memory serves, Garland was FA on a bit of a technicality ... or maybe they were still working out the rules ... but he had only a few years in the bigs, not many innings and became FA following his age 25 season.) And he wasn't as bad as I recalled -- he had a 4 WAR season in Cleveland, a standard 280 IP. Then he got hurt. Reasonably healthy again at 29, he was about average, then done (maybe hurt again). Arguably a less "stupid" signing than the Gerrit Cole contract.

At least Arizona got one year with 31 home runs from him.

Even that managed to be the 4th least valuable 30 homer season in MLB history

Cleveland later masterminded the practice of extending young stars early though ... which is what they were trying to do by signing Garland. (If memory serves, Garland was FA on a bit of a technicality ... or maybe they were still working out the rules ... but he had only a few years in the bigs, not many innings and became FA following his age 25 season.) And he wasn't as bad as I recalled -- he had a 4 WAR season in Cleveland, a standard 280 IP. Then he got hurt. Reasonably healthy again at 29, he was about average, then done (maybe hurt again). Arguably a less "stupid" signing than the Gerrit Cole contract.

There was no minimum years of service requirement initially. Don't know if you just had to have a MLB contract or what. Billy Smith had been with the Angels for parts of 1975 and 1976, mostly minors in 1976. Played out his option, became a FA, signed with the Orioles. Marvin Miller wound up negotiating this right away.

I forgot about Yasmany Tomas

Very similar to the Rusney Castillo contract. Red Sox dfa’d him. Could’t release him or have him up as a backup outfielder, or else the dollars would count against the luxury tax. So he spent 4 years as the richest man in Pawtucket.

Rusney and Crawford (both for the Red Sox!) deserved spots in the OF. There was little reason to think Rusney would be a Major League hitter, and he wasn't. $72 mil wasted. Crawford was $140 mil. for 3.5 WAR. They were both arguably worse than all 3 of Hamilton, Upton, and Belle.

Here’s how I’d look at this systematically.

1. Figure out the going rate for dollars to WAR at the time the deal was signed. You can use a shortcut here, for example if 8 million is the going rate when average team payroll is 120 million, assume 2 million was the going rate when teams has 30 million dollar payrolls.
2. How many wins did the team pay for?
3. How many did he actually produce?

That way you can do a reasonable job comparing Wayne Garland to Josh Hamilton.

And trading Mike Napoli for Vernon Wells isn't even in this discussion :)

This trade created my favorite primate/thinkfactory moment of all time.

First, it's announced that Napoli has been traded to the Jays, with no other information available. Primates are upset because the Angels never gave Napoli a chance. Complaints of Scocia favoring the inferior Mathis. Then, the anger escalates as we learn that the trade involves Wells. I believe it was the first comment of this new post that simply said "lol wut". The absolute perfect response to such absurdity and I reference it at least monthly.

The thread then just kept getting better and better as people speculated on how much money Toronto would have to throw in (50 million?) and what kind of players Toronto would have to add to sweeten it.

As we all know, it would be the Angels throwing in the extra player, and no money was exchanged. I can still taste the rage.

Kronic :


Here is the thread

from the other thread:

32. Rough Carrigan Posted: January 22, 2011 at 02:21 AM (#3734433)
Wow. First the Angels trade for Scott Kazmir just when it's become obvious that he's not the pitcher he was in 2006 and 2007 [....]

..............

[in 2021 - more than a decade after that post - the Giants both won 107 games and gave Scott Kazmir 4 starts. the heart wants what it wants.]

............

77. shock Posted: January 22, 2011 at 03:35 AM (#3734501)

Leaving the money aside

I see no reason why you would do that.

Wells is a Yankee by 2013

.................

[Wells IS a Yankee - in 2013.

March 26, 2013: Traded by the Los Angeles Angels of Anaheim to the New York Yankees for Exicardo Cayones (minors) and Kramer Sneed (minors).

73 starts in LF, 23 in RF, 22 as DH, 1 at 1B

74 OPS+ in 458 PA, released

paired nicely with the rotting corpse of Ichiro and his 77 OPS+ in 555 PA, mostly starts in RF]

Here's an amusing one from the Wells thread:

Now the Halos have Wells penciled in for 2011, 2012, 2013 and 2014(!) to the tune of $20+ million per year? That is the money you could have dangled in front of Albert Pujols - or any other true superstar. This is maddening.

This turned out not to be a problem.

Here is the thread

oooh, updating the email I sent to my friends in 2011. Thanks!!

This turned out not to be a problem.

...for a year or so, and then back into a problem for the next nine.

Primates are upset because the Angels never gave Napoli a chance. Complaints of Scioscia favoring the inferior Mathis

Mike Napoli retired after 2017 and his third stint with the Rangers, always a fan favorite here.

And three years later Jeff Mathis was still catching regularly for the Rangers. I wish I'd predicted that in 2011; nobody would have believed me.

I hate click-bait articles like this, but I had to lick it just to make sure Hundley is the choice at catcher. He is. Thus, I endorse this article.

re Mathis - he was STILL ACTIVE IN 2021.

he went 0 for 9 with 5 K for the Braves, but still.

in 2019, he had an 11 OPS+ in 224 PA for the befuddled Rangers.

career OPS+ of 48 for 6 teams in 17 MLB seasons. he turns 39 on March 31. any GMs out there feel ... lucky?

P.S. He was in a deal that had about as many players who ultimately "mattered" as you'll ever see:

November 19, 2012: Traded by the Toronto Blue Jays with Henderson Alvarez III, Anthony DeSclafani, Yunel Escobar, Adeiny Hechavarria, Jake Marisnick and Justin Nicolino to the Miami Marlins for Emilio Bonifacio, John Buck, Mark Buehrle, Josh Johnson, Jose Reyes and cash.

Yankees fans of a certain age are pretty shocked that this article does not consist entirely Yankees.

Dbacks had Mathis in 2017. BB REF didn't include framing runss in his fielding, so he registered -0.4 WAR in 60 games, but Fangraphs included the framing runs, so he ended up in the black with +0.4 fWAR, so a swing of about 8 runs or so.......maybe, YMMV on framing runs.

Dback fans were apoplectic when Torey Lovullo didn't start Chris Iannetta at catcher in the Wild Card Game against Colorado and again vs LA in Game 1 of the NLDS. Chris had a big year for Arizona that year, 17 hr in 300+ PA and a 120 wRC+. 2.3 fWAR

So of course Mathis had an RBI knock in the Wild Card game and a homer off Kershaw in game 1 of the NLDS to knock him out of the game. Ironically the pitching staff gave up a lot of runs with Mathis behind the plate that post season. In the 3 games he caught they gave up 8,9 & 3 runs for a total of 20. YCPB, amirite ?