It seems crazy today, but at the time, Derrek Lee for Hee Seop Choi was considered a challenge trade.

Beyond that...Kuenn for Colavito? Don Baylor for Mike Easler? Challenge trades of guys playing the same position are so rare.

There was Frisch for Hornsby, but the Giants threw in another player. Texas gave the A's more than just Sierra for Canseco, but I considered that to be something of a challenge trade.

Could Doyle Alexander for John Smoltz count as a challenge trade, or do the two players involved have to be around the same age?  I'd say both teams were happy with how this trade turned out.

One of the freshest challenge trade memory I have from the Blue Jays' past is trading Shawn Green to the Dodgers for Raul Mondesi. Green, after a couple monster years for the Jays, wasn't going to resign with the Jays. Therefore, he was traded to the Dodgers for the disgruntled Mondesi. Growing up as a kid, Green was my favourite player so I was obviously sad to see him leave. Furthermore, Mondesi was atrocious for the Jays over the next couple years, leaving an even more bitter taste in my mouth. To add onto it, Green put up a couple more monster years for the Dodgers. It was an awful trade for the Jays.

slitheringslider (love the name btw),
 
You're clearly letting your memory be colored by the disappointment of losing Green and how Mondesi left Toronto. In 2000, Mondesi was clearly better than Shawn Green or at the very least equivalent (Mondesi was limited to only 99 games but Mondesi had better SLG and the same number of HR in more than 200 fewer ABs). Mondesi had another decent year (OPS+ 106) and then fell off the map. Green had two huge years after his disappointing 2000 and then became average and since turning 30 he isnt' an everyday player. Mondesi's contract was (thankfully) picked up by the Yankees in perhaps the greatest swindle JP puled off... so what am I saying here? Mondesi wasn't atrocious in 2000 and 2001 (as you state) and we didn't lose anything with green who would have left for LA after 2000 (a season in which the Jays got a better player than Green). Don't get me wrong, I've never liked this trade but it wasn't an awful trade for the Jays by any stretch of the imagination the Jays didn't lose anything and gained an exciting (remember the steal of home) player with attitude problems (reminiscent of George Bell in some ways)... sorry for the rambling, but to sum up, yes it was a challenge trade and over the important year (2000) it was a trade won by the Jays as Green would have left after the 2000 season. Mondesi disappeared after 2003 but Green has been over-rated and over-paid since 2003 as well... that said, if Rios were traded for Lincecum, Green would have been a decent fit in RF. Also, I agree he and Carlos were wonderful to watch on the under-rated 1998 and 1999 Blue Jays teams.

Ozzie Smith for Garry Templeton always sticks out in my mind.

From Baseball-Reference:
December 10, 1981: Traded by the San Diego Padres with a player to be named later and Steve Mura to the St. Louis Cardinals for a player to be named later, Sixto Lezcano, and Garry Templeton. The San Diego Padres sent Al Olmsted (February 19, 1982) to the St. Louis Cardinals to complete the trade. The St. Louis Cardinals sent Luis DeLeon (February 19, 1982) to the San Diego Padres to complete the trade.

Ozzie was 4 years into his career and while a great gloveman (he'd won Gold Glove awards in '80 & '81) had only topped .230 AVG once during that time. He'd averaged a 65 OPS+ and was coming off a year in which he ran a .222 / .294 / .256 line with only 22 SBs vs 12 CS.

Garry Templeton was actually two years younger, but had been in the league for 6 years at the time of the trade. He was a career .300 hitter who had twice posted 200 hit seasons and had rougly a 102 OPS+ for his career. He was coming off a .288 / .315 / .393 year, with only 8 SBs - his worst season since his rookie year. He was also a hazard defensively, once making 40 errors in a season, twice topping 30, and another at 29. I realize this is a basic look at his defensive abilities, but clearly, the teams were dealing a glove for a bat.

In the end, we all know St. Louis got the better part of the deal. Templeton never again topped 100 OPS+ but was SD's regular SS for the next decade regardless.

Ozzie was the starting SS in StL for 13-14 years and topped 100 OPS+ 4 times during that span, with his best season being a 2nd place MVP finish in 1987 - .303 / .392 / .383 with 105 OPS+. He continued to steal bases, averaging about 35 a year, and continued to be an outstanding defensive shortstop.

I was hoping to pull career win shares figures for both players, but couldn't find them online. Can someone tell me where historical WS figures reside?

Gary Templeton for Ozzie Smith, San Diego and St. Louis, when both were young, established shortstops entering their prime (about 1980-- I'm too lazy to look it up...)

 

 

 

I don't mean to sidetrack this discussion, but RIP, Johnny Podres.

My memory may be faulty because the info is coming from me recall of baseball cards when I was a kid, but didn't Buddy Bell get traded straight up for Toby Harrah? That would be a challenge trade, no?

Good call, rpriske -- in the '78 offseason, the Indians traded the 30-year-old Bell to the Rangers for the 27-year-old Harrah.  Both were fine players who did well with their new teams, and they were even briefly teammates in '85 when Harrah returned to Texas before Bell was traded to Cincinnati for Duane Walker and a PTBNL who turned out to be Jeff Russell.

The Indians dumped Harrah on the spendaholic Yankees of the '80s for a package centered around Otis Nixon and George Frazier.  Harrah made one All-Star team with the Indians while Bell made four with the Rangers and brought a better package back in return (though nobody knew Russell would become a multiple 30-save-season guy at the time) ... I think the Rangers pretty clearly "won" that one, no?

One of my favourites was the Fullmer/Segui/Stevens three-way challenge. The Jays won that one in the short term, but it didn't really make an impact for anyone in the long-term.

Would Doyle Alexander for John Smoltz qualify? Same position, but more of a winter-spring challenge. 

And I'm certain Doyle Alexander for Duane Ward doesn't hit the mark. No SP for RP, I gather.

I'm surprised nobody has mentioned this one yet: George Bell for Sammy Sosa.

Winners above (need I mention): the team not acquiring Doyle or George.

I guess the Clemens- Wells trade was packed with other pieces of notable value to prevent it from being a head-on challenge trade, but how about the Wells-Sirotka trade?

I thought the Devon White trade might qualify, but I see it was essentially Junior Felix and Luis Sojo for White.  Then there's Gruber for Sojo two years later -- yet Sojo was primarily a 2B.

Nearly a challenge trade: Carl Pavano and a PTBNL for Pedro Martinez.

PTBNL:  Tony Armas.

Scott Kazmir for Zambrano (essentially -- wouldn't you say?).

Who could forget the big swap of first basemen/designated hitters Al Oliver and Len Matuszek!