6. Darrin Jackson
First Tenure: 1994, .312/.362/.444
Second Stay: 1999, .275/.288/.430
Jackson was part of the most infamous "What If" White Sox team of the modern era, the 1994 team that had its chance to win a World Series wiped away by baseball's strike that season. Jackson enjoyed what was probably his finest professional season that summer, hitting well and playing a good right field, just like Ellis Burks -- the team's previous stopgap solution in right -- did the year before.
The Sox looked much different when Jackson returned a few years later after a couple seasons in Japan, and stops in Minnesota and Milwaukee. Gone were all of the players from the previous team who might have made a title run, except for Frank Thomas, around whom the Sox were trying to build a new core of young players.
Jackson was different, too. Instead of a starting right fielder, he played as a fourth outfielder. What was so disappointing about Jackson's return wasn't so much his play in that role, or the sad reminder of the last talented team that collapsed, but that the Sox had an abundance of young outfielders who needed looks.
Three of those those young outfielders did emerge with firm holds on jobs by the end of the year (Magglio Ordonez, Carlos Lee and Chris Singleton), and among the others who auditioned (Jeff Liefer, Jeff Abbott, McKay Christensen and Brian Simmons), the most noteworthy thing any of them did after leaving the Sox was when one of them locked himself in the bathroom during a game. So in that sense it didn't cost the franchise any opportunity to let a kid run with a job. And Jackson was so well-liked he remained with the team, first in the TV booth before moving over to radio.
Still, even season ticket holders weren't interested in watching Jackson start half the games in center field, which knowing how then-manager Jerry Manuel liked to run things, might have been a job-share that persisted had Jackson dropped in a few more singles.
5. Sandy Alomar
First Tenure: 2001-2002, .264/.296/.382, then 2003-2004, .254/.289/.365
Third Stay: 2006, .217/.255/.358
Perhaps the biggest laugher in the "Trade for an Alomar!" jokes longtime general manager Ken Williams wrote in the early and middle parts of the previous decade.
The first time the Sox brought in Alomar, they needed a catcher. After trading him to Colorado, they brought him back again as a veteran caddy for a young Miguel Olivo. Then Olivo was traded, and Alomar could not credibly start over Ben Davis. That's OK. Life is rough for catchers near the end of their careers. A.J. Pierzynski fell in the Sox's laps that offseason, and catcher wasn't a huge concern for nearly a decade.
Then when the Sox began spinning their wheels during July of their 2006 title defense, they reached for the old security blanket by bringing Alomar back again, this time in a trade with the Dodgers for some guy you've never heard of.
It's not that Alomar was costly. It's not that he wasn't marginally better than they guy he replaced (Chris Widger). It's not like he even mattered in his 19 games played behind the workhorse Pierzynski. He was a backup catcher, so who cares?
It was just the pointlessness of it. Trading for a guy who was barely better than the incumbent, who probably wasn't at all better than Chris Stewart, who wasn't all that good either, and who wasn't even going to play much, all while there were much bigger issues.
4. Roberto Alomar
First Tenure: 2003, .253/.330/.340
Second Stay: 2004, .180/.203/.449
Again, it's hard to see past the pointlessness of this one. Alomar was a shell of himself when the Sox traded for him to man second base in 2003. When it turns out the contract Alomar and Williams worked out with a handshake, on a bar napkin, or whatever was alleged, Alomar took his steeply declining career to Arizona for even less money.
The decline was so steep that Alomar, Utility Infielder of '04 was even more disappointing than Alomar, Second Baseman '03.
The only happy part of this reunion story is that Williams and the Sox weren't out the money they would have been if Alomar had been cornered without his agent.
3. Esteban Loaiza
First Tenure: 2003-04, 30-14, 3.65 ERA
Second Tenure: 0-0, 6.80 ERA, 3 IP
Loaiza was the first, and maybe remains the most famous of Sox pitching coach Don Cooper's reclamation projects. A journeyman in his 30s when he joined the Sox as a minor league free agent before 2003, Loaiza learned a cutter and finished second in the Cy Young voting that season while going 21-9 with a 2.90 ERA.
His second season in Chicago was a little rougher, and with no contract extension likely to be worked out, he was traded for Jose Contreras.
The Sox must have remembered his success with them fondly, because despite only one solid season after his exodus from the team, they brought him back for a look after he was released by the Dodgers during the 2008 season.
Be it that the end was near all along, or rumors that Loaiza wasn't working out and in game shape between stays in organizations, he never recaptured his stuff.
2. Bartolo Colon
First Tenure: 2003, 15-13, 3.87
Second Stay: 2009, 3-6, 4.19 ERA, 13 unearned runs, 13 HR allowed in 62 1/3 IP
Colon couldn't quite put the White Sox over the top and into the playoffs during his first stay, but rode a gaudy win total to a Cy Young Award a couple seasons later in Anaheim. Always an innings eater, and probably an eater of many other delicious things, his massive workload that year probably set the stage for the health problems that plagued him since, and only ended once he found a unique medical treatment.
It wasn't just the results that were a letdown from Colon, though that was less than expected, too. It's that while battling injuries, he also went missing for a time, leading to some amusing speculation that it had something to do with the King of Pop's demise.
Despite a drug suspension stemming from his treatments, Colon has been back. A couple solid seasons in Oakland even helped him sign another albatross contract the Mets would be happy to unload right now. Don't look for them to unload it on the Sox now.
1. Harold Baines
First Tenure: 1980-89, 1996-97, .288/.346/.463, 220 HR
Third Stay: .166/.240/.225, 1 HR
The first reunion was great, despite the circumstances surrounding it. The third and final reunion cut deeply into Baines' playing time as he was added via trade to be a bench bat for an ill-fated playoff run in 2000.
At the time the Sox picked him up from Baltimore, Baines was batting .266/.349/.437 with 10 home runs. This was coming off a .312/.395/.533 year with 25 home runs split between Baltimore and Cleveland. With 2,842 hits in his career, Baines looked to be one and a half healthy seasons away from reaching the 3,000 milestone that might have bolstered his Hall of Fame case.
Hindsight tells us 3,000 probably wasn't in the cards for Baines. If he declined between 1999 and 2000, then he absolutely fell off a cliff after the trade back to the White Sox. He hit only one more home run in his career, on Aug. 15, 2000, appropriately against Baltimore. With a double that night he also had his last multi-hit game.
Baines came back with the Sox in 2001, presumably in the same bench role he occupied down the stretch the previous season. Even when a season-ending injury to Frank Thomas opened the door for playing time to rebound from a .105/.150/.105 start and start marching up the career hit list, Baines couldn't answer the bell. He finished May with a barely improved line of .117/.187/.130. Because of injuries and ineffectiveness, he played three more games, collected two more hits, and came to the plate a final time on Sept. 27 as a pinch hitter, striking out to close his career.
What was most disappointing about this reunion was that if everything had worked out as planned, the Sox would storm to another division title like they had with a young team the year before, Baines would add a few more marks on his record sheet, but probably come up short of making things tough for Hall of Fame voters.
When Thomas got hurt and contention fell through, the would-be consolation prize -- watching an old hero get a legitimate run at 3,000 hits -- also evaporated.
Even if Baines had no real shot at matching the hopes of wishful White Sox fans, in a way it was still like watching the present burn and the past fade at the same time. Or like with Jackson, for Sox fans it was facing an uncertain future while holding on to a past we couldn't make more glorious.
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