The table below shows these stats over the course of his career. Data from Baseball Reference.
These last two years his OPS+ has been well above anything he ever did before. He has his lowest strikeout rate in 8 years and his lowest GDP rate in 6 years (for strikeout rate it was K/PA with IBBs taken out-GDP rate is GDPs divided by opportunitites). He his making more contact which should make more GDPs a possibility but he is avoiding them more than in the past (see what I say below as to how his low 2005 GDP rate is another example of how lucky the Sox were that year).
The chart below shows Konerko's OPS+ over time.
A regression with OPS+ as the dependent variable and year as the independent variable yields an r-squared of .4 and the trend line is positive. He did not peak before 30 like most guys and then trend downwards
Now for the strikeout rate and the GDP rate.
Except for that wild fluctuation in the middle of his career, his GDP rate seems to be trending downward. He has always been slow but his GDP rate is not rising as he ages.
I think it is interesting that his GDP rate took such a big dip in 2005. He only grounded into 9 double plays that year. The year before it was 23 and the next year it was 25. Hitting into 10-15 fewer DPs must have really helped the Sox that year. This may be another way they were lucky that year. The Sox had to go down to the last week of the season before they clinched a playoff spot. It was not a sure thing. They beat their main competitor, the Indians something like 14 out of 19 that year and won a bunch of 1-run games that year against them. Konerko not hitting into DPs must have helped quite a bit. Click here to read about a bunch of other ways the Sox were lucky that year that I wrote about. For one, they got great years out of relievers Politte and Cotts who did not do much before or after that season.