He's cobbled together 30 different permutations this year, but try as he might, can't seem to unlock the combination to get the bats going.
Coming into Thursday's game against the Los Angeles Angels, the White Sox had the worst batting average in baseball and the fewest hits in the American League. Interestingly enough, they'd struck out the fewest times in the league.
They're putting it in play, just not particularly hard. For the sabremetric enthusiasts: their BABIP (batting average on balls in play) is underwhelming.
Considering their troubles, it certainly doesn't help when the ball bounces against them.
That was the case in the eighth inning when A.J. Pierzynksi's bases-loaded double, which would have tied the game at 6-all, bounded over the left-field wall, sending the speedy Juan Pierre back to third base.
Andruw Jones proceeded to fly out to center to end the late threat as the Sox lost their second straight to the Angels.
"We bounced back," said Guillen of the eighth inning, which began with his club facing a five-run deficit. "It's fun when you see guys attacking and score some runs and swing the bat well. You don't see that too often this year. When you see that, you get a little excited, but we just came up short once again."
The simple truth is, that despite four-plus months remaining on the schedule, the Sox have built themselves a serious hole in the AL Central by coming up short too often. They'll have to overcome not one, but two seven-and-a-half-game deficits. The teams they're chasing - the Minnesota Twins and Detroit Tigers - have both looked vastly more consistent than the club playing on the South Side.
It's becoming a daily occurrence, the post-game mantra that this team will turn it around, that they're just too good not to get on the right track.
"It was too little, too late, but it's tough," first baseman Paul Konerko said after this loss, which dropped the Sox eight games under .500 for the first time this year. "We are trying to go about it right and play the game hard and trust that it will bring wins.
"It's not doing that on a consistent basis at all. It's frustrating. You just got to take satisfaction that we went out and did it right. If you keep doing it, it will turn."
For every vote of future confidence, there's a number that reflects just how bad it's been.
For instance, the highest average in the starting lineup Thursday was the .272 brought in Konerko. Not exactly a murder's row to instill fear into the opposing starter.
You can preach pitching and defense all you want, but eventually pushing some runners across the plate becomes a necessity. The grinder-ball machine needs some grease every now and again.
The Sox would prefer that the cylinders start firing before it's too late.