The centerpiece of the legend of the Almanac Trial is Lincoln’s cross-examination of the eyewitness to the killing. Was he really a good cross-examiner? Frederick Trevor Hill, who wrote the first book about Lincoln’s law practice seems to have thought so. Hill said:
Cross-examination makes greater demands upon a lawyer than any other phase of trial work, and it has been rightly termed an art. To succeed in it the practitioner must be versed in the rules of evidence; he must be familiar with all the facts in his case, and keep them continually in his mind; he must think logically, be far-sighted, tactful, and a keen judge of human nature. All these qualities Lincoln possessed to an unusual degree. … Lincoln the Lawyer, pp. 226, 227.
At the 1912 convention of the Illinois State’s Attorneys Association, Joseph Benjamin Oakleaf gave a speech in which he described Lincoln's method of cross-examining:
One reason why I think he would have been a successful criminal lawyer was his mastery of the art of cross examination, in which he had no equal. If any obstinate witness appeared and was determined to conceal facts which Lincoln desired brought out, Lincoln would neither show resentment nor attempt to coerce the witness but would go after him in a nice, friendly way, questioning about things which were foreign to the point desired, thus placing him at ease, making him forget his antagonistic ideas, and, before he was aware of the harm he was doing his side, the whole story would be laid bare, and then Lincoln would compliment the witness on his fairness and the witness would consider himself a hero. Abraham Lincoln as a Criminal Lawyer, p. 6.
We have more than Oakleaf’s description of Lincoln’s methods as a cross-examiner. We have the account of James Hoblit, a witness whom Lincoln actually cross-examined. We will let Hoblit tell the story in his own words:
I shall never forget my experience with him. I was subpoenaed in a case brought by one Paullin against my uncle, and I knew too much about the matter in dispute for my uncle's good, The case was not of vital importance, but it seemed very serious to me, for I was a mere boy at the time. Mr. Paullin had owned a bull which was continually raiding his neighbor's corn, and one day my uncle ordered his boys to drive the animal out of his fields, and not to use it too gently, either. Well, the boys obeyed the orders only too literally, for one of them harpooned the bull with a pitchfork, injuring it permanently, and I saw enough of the occurrence to make me a dangerous witness.
The result was that Paullin sued my uncle, the boys were indicted for malicious mischief, Mr. Lincoln was retained by the plaintiff, who was determined to make an example of somebody, and I was subpoenaed as a witness. My testimony was, of course, of the highest possible importance, because the plaintiff couldn't make my cousins testify, and I had every reason to want to forget what I had seen, and though pretty frightened, I determined, when I took the stand, to say as little as possible. Well, as soon as I told Mr. Lincoln my full name he became very much interested, asking me if I wasn't some relative of his old friend John Hoblit who kept the house between Springfield and Bloomington; and when I answered that he was my grandfather, Mr. Lincoln grew very friendly, plying me with all sorts of questions about family matters, which put me completely at my ease, and before I knew what was happening, I had forgotten to be hostile and he had the whole story. After the trial he met me outside the court-room and stopped to tell me that he knew I hadn't wanted to say anything against my people, but that though he sympathized with me, I had acted rightly and no one could criticize me for what I had done. The whole matter was afterward adjusted, but I never forgot his friendly and encouraging words at a time when I needed sympathy and consolation. Lincoln the Lawyer, pp. 225, 226.
There's an old proverb about lawyering that goes "When you cross-examine, you don't have to examine crossly." Lincoln exemplified that proverb.