Sen. Sheldon Whitehouse (D-R.I.) on Tuesday sent 14 pages of questions to Supreme Court nominee Brett M. Kavanaugh. While Whitehouse covers a lot of ground — from abortion, to environmental regulations, to work Kavanaugh performed in the George W. Bush administration — two things stand out.

First, he asks a ton of questions about the judge’s finances, including “Are there any debts, creditors, or related items that you did not disclose on your FBI disclosures?” He asks a slew of questions about the debt Kavanaugh incurred allegedly paying for baseball tickets for a friend who reimbursed him, as well as how he could afford membership at the Chevy Chase Club, which reportedly has a $92,000 initiation free and annual dues of more than $9,000.

Whitehouse also inquired whether Kavanaugh “participated in any form of gambling or game of chance or skill with monetary stakes, including but not limited to poker, dice, golf, sports betting, blackjack, and craps.” He even goes so far as to inquire whether Kavanaugh “ever sought treatment for a gambling addiction.”

Is this a Hail Mary, or does Whitehouse have something? Presumably anything untoward would have come up already, but if Whitehouse, a former federal prosecutor and state attorney general, has something concrete — as opposed to the nothingburger inquiry Sen. Kamala D. Harris (D-Calif.) made as to whether Kavanaugh spoke to someone at Trump’s lawyer’s firm about the Mueller investigation — this might be the October (or September) surprise to end all surprises. Whitehouse’s office declined to elaborate.

The second and, perhaps, more fundamental area of inquiry has to do with Kavanaugh’s views on executive power. In his testimony to the Senate Judiciary Committee, Kavanaugh gave not an ounce of reassurance to any senator concerned about executive power. It’s a measure of the degree to which the White House assumes all Republican votes are locked up that Kavanaugh brushed off questions not only from Democrats, but from independent-minded Sen. Jeff Flake (R-Ariz.). Whitehouse asked: “Under current law, what rights does Congress have to documents, materials, and testimony vis-à-vis claims of executive privilege?” He also asked a batch of questions on U.S. v. Nixon:

1. In an exchange with Senator [Lindsey O.] Graham during your hearing before the Committee, you explained, “the Nixon holding said that, in the context of the specific regulations there, that a criminal trial subpoena to the president for information — in that case, the tapes — could be enforced, notwithstanding the executive privilege that was recognized in that case, as rooted in Article II of the Constitution.”
a. What are the “specific regulations” to which you referred when discussing United States v. Nixon?
b. Is it your view that the “specific regulations” referenced in (a) were dispositive to the overall holding of the case?
2. On at least five occasions when referencing the Nixon precedent during the hearings, you made a point of noting that the subpoena at issue in that case was a criminal trial subpoena.
a. What role did the fact that the subpoena in Nixon originated from a district court, rather than a grand jury, play in the Court’s analysis?
b. Was the fact that the subpoena was a trial subpoena dispositive to the Court’s holding that the constitutionally protected executive privilege was not absolute and that the President had to respond thereto?
c. Does Nixon control with respect to questions relating to subpoenas of the president issued by a grand jury?
d. Does Nixon control with respect to cases involving congressional subpoenas to the president?
e. Does Nixon control with respect to cases involving administrative subpoenas to the president?
f. Does Nixon control with respect to cases involving subpoenas to the president issued in state trial proceedings?
g. Does Nixon control with respect to cases involving subpoenas to the president issued by state officials?
h. Does Nixon control with respect to cases involving subpoenas to the president issued by state grand juries?
i. As you know, the Nixon case involved a subpoena for tape recordings. Does the precedent apply to cases involving subpoenas for presidential testimony as well as documentary evidence in the president’s possession, custody, and control?

Should Kavanaugh play the same “I can’t comment on an issue that might come up,” Democrats will no doubt push their GOP colleagues. Do you really want to vote for someone who’s going to hand Trump a figurative get-out-of-jail-free card? Do you want to be responsible for a constitutional crisis? It is the one issue, beyond abortion, that might raise real concerns among Republicans who say they are troubled about Trump’s antidemocratic power grabs. On the other hand, you never go wrong betting on Republicans’ utter lack of spine or sense of responsibility.

Whitehouse’s questions, in short, are precisely the kind of inquiries you want asked of a Supreme Court nominee. However, put me down as skeptical that the senator’s going to get direct answers.