10 Of My Favorite White Sox “Win Now” Acquisitions Of The Last Ten Years

Not that the good times are here yet for the White Sox, but sometimes it’s fun to look back at the REALLY dark times and laugh.

Sadly, those dark times stretched from 2008 until we traded Chris Sale. When thinking of that time period, my mind begins wandering to some of those juicy Kenny Williams signings.

Without further ado, here are my ten favorite “win now” White Sox acquisitions dating back to the last time the Sox made a playoff appearance (2008).

10. JAKE PEAVY (2009 – 2013)

(photo via Jesse Johnson-US PRESSWIRE)

How We Got Him: Traded from the San Diego Padres for Clayton Richard, Aaron Poreda, Dexter Carter and Adam Russell

How Did He Do: (84 G) 36-29, 4.00 ERA, 1.16 WHIP

I completely get that Jake Peavy’s time with the White Sox altogether wasn’t too bad. However, if you take out his final year in 2012 (when he was an All-Star), it could’ve been ugly.

He came over in a trade with the Padres where the Sox gave up next-to-nothing. Clayton Richard is the only one of the four who did anything, but even his career hasn’t been stellar.

2010 and ’11 were pretty terrible for Peavy as he posted ERA’s of 4.63 and 4.92, respectively, while throwing just 107 and 111.2 innings. It’d be a little different if he had been able to stay healthy and eat up more innings. Like I mentioned, though, he redeemed himself in 2012 with 219 innings and a squeaky clean 3.37 ERA.

So, sorry Jake Peavy. You probably don’t deserve to be on this list; but more than anything it’s guilt by association for the time period in which you were acquired.

9. MARK KOTSAY (2009 – 2010)

(photo via gettyimages)

How We Got Him: Traded from the Boston Red Sox for Brian Anderson

How Did He Do: (147 G) .252/.318/.391, 11 HR, 49 RBI

Not that Mark Kotsay was ever a high-profile player, but he had a couple of good years in Oakland; specifically 2004 when he finished 14th in the MVP voting.

When he first came over from Boston he had a decent 40 game stretch with the Sox, hitting .292 with an OBP near .350. He was able to use that little bit of action to trick ole’ Kenny Williams into a one-year deal for his age 34 season. Kotsay then picked up just 31 RBI in 359 plate appearances. PRODUCTION.

8. JUAN PIERRE (2010 – 2011)

juan pierre
(photo via Keith Allison//CC License)

How We Got Him: Traded from the Los Angeles Dodgers for John Ely and Jon Link

How Did He Do: (318 G) .277/.335/.322, 3 HR, 97 RBI, 95 SB

The Sox were looking for a leadoff man at the time and they got one in the form of Pierre. In exchange, they traded away Jon Link, and my soon-to-be brother-in-law, John Ely. Link did nothing, while Ely had a nice stint with the Dodgers until, unfortunately, Tommy John surgery reared its ugly head.

For the most part, Pierre did what he was supposed to for the Sox. Got on base at an okay clip, stole a couple bases (a lot in 2010: 68) and didn’t provide any power.

Still, given that he was 32 at the time of the trade, it can be remembered as a very classic White Sox “win now” acquisition.


(photo via Brian Cassella, Chicago Tribune)

How We Got Him: Signed for one year/$1 million

How Did He Do: (24 g) .171/.294/.195, 0 HR, 4 RBI

One man’s trash is another man’s trash.

It’s not like we invested anything in the former-Cub with $1 mil guaranteed, it’s just funny more than anything. Honestly, I feel as though he was signed with the hope that he might do anything at all and make Jim Hendry and the North-siders look silly.


He stepped up to the plate 51 times in a White Sox uniform, reaching base fifteen times and striking out nine times.

Also, it’s definitely not on the market anymore, but Fukudome was selling his Streeterville condo back in 2016. He probably had enough of Chicago.


(photo via Bleacher Report)

How We Got Him: Traded from the Boston Red Sox for Brent Lillibridge and Zach Stewart

How Did He Do: (80 g) .236/.346/.425, 15 HR, 46 RBI

The White Sox got Kevin Youkilis, fresh off an All-Star season with the Red Sox, at a time when they were winning the AL Central. They of course did not win the AL Central that year.

He was supposed to be one of the last pieces to the puzzle as we sorely needed a third baseman at the time. I distinctly remember being very excited about the trade, and all things considered I guess it didn’t go too horribly outside of his .236 batting average. He hit a decent amount of home runs and stayed on the field. For that I say thank you, Kevin.

However, as most White Sox acquisition went during this time period, Youkilis’s time in Chicago essentially represented the end of his career. He would go on to play just 28 games with the Yankees in 2013 before retiring.

5. OMAR VIZQUEL (2010 – 2011)

Omar Vizquel, Alexei Ramirez

How We Got Him: Signed for 1 year/$1.375 million

How Did He Do: (166 g) .268/.324/.323, 2 HR, 38 RBI, 12 SB

I suppose looking back on it, signing Omar Vizquel did more long-term good than anything. He acted as a pretty good mentor for Alexei Ramirez and even ended up as manager of our Class-A team, the Winston Salem Dash.

Still, signing a well-out-of-his-prime 43-year-old shortstop was sooooo 2010 White Sox.

With everything in perspective, I suppose a .268 batting average for a guy in his mid-forties isn’t too bad; neither is twelve stolen bases (though he was caught nine times).

Vizquel is just the tipping point of old dude White Sox signings that remain on this list.

4. ADAM DUNN (2011 – 2014)

Rick Osentoski-USA TODAY Sports

How We Got Him: Signed for four years/$56 million

How Did He Do: (528 g) .201/.321/.410, 106 HR, 278 RBI

For better or worse, Adam Dunn will forever live prominently in my White Sox memory. His signing was the definition of “win now” as back in 2011 the Sox slogan was literally, “all in.”

We signed him off a pair of anomaly seasons where Dunn was able to post batting averages of .260+, something he wasn’t even able to come close to touching for the rest of his career. Looking back on it now, .260 for the Swamp Donkey was like any other player hitting .350.

He nearly made history during the 2012 season striking out a mind-numbing 222 times.

Two. Hundred. Twenty. Two. That means Dunn struck out 34.2% of the time he stepped into a batters box that season.


The number is the second-highest in the history of baseball, second to only Mark Reynolds who whiffed an even more incredible 223 times in 2009.

It’s possible that nobody represents the dark period of White Sox baseball more than Adam Dunn.

3. ANDRUW JONES (2010)


How We Got Him: Signed for one year/$500,000

How Did He Do: (107 g) .230/.341/.486, 19 HR, 48 RBI

Now we start the run of my three favorite post-prime White Sox acquisitions.

Jones is a guy that the Sox actually tried to get from the Braves when he was still a perennial All-Star. Obviously that didn’t happen; but better yet, we got him when he was washed up!

My last line reminded me of Step Brothers. Sorry.

Nineteen dingers ain’t bad, especially for a guy who wasn’t brought in to start, and he did have his highest average since 2006, the last time he was an All-Star.

Keeping up with the theme; Jones would go on to play just 171 more games after his stint with the White Sox.

2. KEN GRIFFEY JR. (2008)

(Jonathan Daniel/Getty Images North America)

How We Got Him: Traded from the Cincinnati Reds for Nick Masset and Danny Richar

How Did He Do: (41 g) .260/.347/.405, 3 HR, 18 RBI

How disgusting is it that the last time the Sox played a playoff game, Ken Griffey Jr. was on the roster. Typing that hurts my heart. The funny thing is, Griffey approved the trade from the Reds to the Sox in hopes of playing in the World Series for the first time in his career. It’s an actual shame that we only got to see KGJ play 18 playoff games across his 23-year career. Not that I knew baseball existed until about nine years into it.

Blackout game though.



How We Got Him: Traded from the Los Angeles Dodgers for salary relief

How Did He Do: (24 g) .261/.420/.319, 1 HR, 2 RBI

Ramirez was a late-season, desperation acquisition for a White Sox team that was willing to do literally anything to make the playoffs. That sentence right there is dripping with Kenny Williams’ blood.

I’m not trying to do this, but I’m going to: Ramirez sported a .420 OBP over 69 at-bats with the White Sox. Some sentences write themselves.

Believe it or not, ManRam is supposedly still playing ball today at age 45 for the Kōchi Fighting Dogs, although the team’s website doesn’t officially list him.

Thanks for the memories, Manny.

SIDE NOTE: obviously this turned out to be less of a “ranking” and more of a “let’s look back at ten of the funniest White Sox acquisitions of the last ten years.” Either way, hope you enjoyed.

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