Respondent filed an opening brief on July 9, 2012. Petitioner did not file an 2012 Tax Ct. Memo LEXIS 313">*319 opening brief. In the light of petitioner's failure to file an opening brief, on August 17, 2012, we ordered that the record in this case be closed. On August 31, 2012, petitioner filed a "motion to reopen proceedings to permit respondent [sic] to file reply brief" (motion to reopen proceedings). Petitioner's motion to reopen proceedings was denied by the Court on September 4, 2012.

Rule 151(a) requires that briefs are filed after trial, except as otherwise directed by the presiding Judge. Rule 151(b) allows the presiding Judge to direct the parties to file either simultaneous briefs or seriatim briefs. Rule 151(c) provides that simultaneous briefs "shall be served by the Clerk after the corresponding brief of the other party has been filed". In other words, if the presiding Judge directs the parties to file simultaneous briefs under Rule 151(c) then the briefs are served on the parties after each party has filed their respective brief with the Court.

*320 There were 117 exhibits, totaling 1,820 pages, entered into evidence. The documents petitioner provided were not self-explanatory. Petitioner's testimony was general and did not clearly explain or link the exhibits to his claimed 2012 Tax Ct. Memo LEXIS 313">*320 deductions. Petitioner's testimony was in large part a criticism of the Internal Revenue Service. Additionally, petitioner's testimony on cross-examination indicated that many of his claimed deductions appeared to be founded on frivolous legal reasoning. As a result, at the close of trial the Court directed the parties to file simultaneous opening briefs on July 9, 2012, explaining how the exhibits and testimony supported their positions. Respondent timely filed a detailed opening brief. Petitioner failed to file an opening brief. On August 17, 2012, after waiting 34 days from the date on which petitioner had been ordered to file a brief, we closed the record.

Petitioner claims that he did not file a brief because he did not receive respondent's brief. Petitioner's excuse makes no sense. Our order was that petitioner and respondent file simultaneous opening briefs on July 9, 2012. Rule 151(c) explicitly requires that simultaneous briefs shall be served "after the corresponding brief of the other party has been filed". ⁴ Petitioner's failure to file *321 an opening brief is particularly egregious in the light of his prior history of failure to adhere to the Court's Rules, the Court's specific 2012 Tax Ct. Memo LEXIS 313">*321 orders, and the fact that petitioner is an attorney admitted to practice before the U.S. Tax Court. By not filing an opening brief with the Court, petitioner has failed to comply with Rule 151 and a direct order of the Court. See also Mock v. Commissioner, T.C. Memo. 1987-382, 1987 Tax Ct. Memo LEXIS 380">1987 Tax Ct. Memo LEXIS 380, at *1987 Tax Ct. Memo LEXIS 380">5 ("The provisions of Rule 151 are not permissive but mandatory.").

Rule 123(a) provides that if any party has failed to proceed as required by the Court, then such party may be held in default and a decision may be entered against such party. Rule 123(b) provides that if a party fails to comply with any order of the Court, the Court may decide against such party on any issue as to which the party has the burden of proof. Petitioner had the burden of proof on all issues.

"Petitioner had an obligation to assist the Court by organizing the material presented at trial, which was extensive, and giving the Court his views of the controlling legal authorities." Mock v. Commissioner, T.C. Memo 1987-382, 1987 Tax Ct. Memo LEXIS 380">1987 Tax Ct. Memo LEXIS 380, at *1987 Tax Ct. Memo LEXIS 380">5-*6. A 2012 Tax Ct. Memo LEXIS 313">*322 taxpayer's failure to file a brief "fully justifies the dismissal of all issues as to which * * * [petitioner has] the burden of proof." Stringer v. Commissioner, 84 T.C. 693">84 T.C. 693, 84 T.C. 693">708 (1985), aff'd without published*322 opinion, 789 F.2d 917">789 F.2d 917 (4th Cir. 1986). The failure of a party "to comply with the dictates of Rule 151 and the specific directions of the Court, can be said to constitute a default under Rule 123(a)". 84 T.C. 693">Id. at 706. Petitioner failed to comply with the Court's orders to: (1) file a pretrial memorandum; (2) prepare for and be ready for trial; (3) answer respondent's interrogatories and respond to respondent's request for production of documents; and (4) file a posttrial brief. As a result of his continued failure to comply with the orders of this Court, and specifically his failure to file an opening brief, we hold that petitioner has failed to properly prosecute his case and is in default.

The proper remedy is to decide against petitioner, pursuant to Rule 123, on all issues on which he has the burden of proof. See 84 T.C. 693">id. at 704-708; Hartman v. Commissioner, T.C. Memo. 1999-176, 1999 Tax Ct. Memo LEXIS 213">1999 Tax Ct. Memo LEXIS 213, at *1999 Tax Ct. Memo LEXIS 213">17-*18; Abeson v. Commissioner, T.C. Memo. 1990-190, 1990 Tax Ct. Memo LEXIS 210">1990 Tax Ct. Memo LEXIS 210, at *1990 Tax Ct. Memo LEXIS 210">14-*15, 2012 Tax Ct. Memo LEXIS 313">*323 aff'd without published opinion sub nom. Rivera v. Commissioner, 959 F.2d 241">959 F.2d 241 (9th Cir. 1992). Petitioner had the burden of proof on all issues. SeeRule 142(a); INDOPCO, Inc. v. Commissioner, 503 U.S. 79">503 U.S. 79, 503 U.S. 79">84, 112 S. Ct. 1039">112 S. Ct. 1039, 117 L. Ed. 2d 226">117 L. Ed. 2d 226 (1992); New Colonial Ice Co. v. Helvering, 292 U.S. 435">292 U.S. 435, 292 U.S. 435">440, 54 S. Ct. 788">54 S. Ct. 788, 78 L. Ed. 1348">78 L. Ed. 1348, 1934-1 C.B. 194 (1934). In some cases the burden of proof with respect to relevant factual issues may shift to the Commissioner under section 7491(a). However, petitioner has not argued that the *323 burden of proof should shift to respondent, nor has he maintained all required records and cooperated with respondent's requests as required by section 7491(a)(2)(A) and (B). Accordingly, we sustain respondent's determination regarding the underlying tax deficiencies. ⁵

Respondent determined that petitioner was liable for section 6662(a) accuracy-related penalties 2012 Tax Ct. Memo LEXIS 313">*324 of $10,665 and $13,187 for the taxable years 2005 and 2006, respectively. Section 6662(a) imposes an accuracy-related penalty equal to 20% of the underpayment to which section 6662 applies. Section 6662 applies to the portion of any underpayment which is attributable to, inter alia, negligence or disregard of rules or regulations, sec. 6662(b)(1), or a substantial understatement of income tax, sec. 6662(b)(2).

Section 7491(c) provides that the Commissioner bears the "burden of production" with regard to penalties and must come forward with sufficient evidence indicating that it is appropriate to impose the penalty. See Higbee v. Comm'r, 116 T.C. 438">116 T.C. 438, 116 T.C. 438">446 (2001). Once the Commissioner meets his "burden of production", however, the "burden of proof" remains with the taxpayer, *324 including the burden of proving that the penalty is inappropriate because of reasonable cause under section 6664. SeeRule 142(a); Higbee v. Commissioner, 116 T.C. 438">116 T.C. 446-447.

Respondent contends that the underpayments of tax are attributable to either negligence or substantial understatements of income tax. Respondent's contentions necessarily reflect alternative grounds for imposing the section 6662 penalties 2012 Tax Ct. Memo LEXIS 313">*325 because only one section 6662 accuracy-related penalty may be imposed with respect to any given portion of any underpayment, even if the underpayment is attributable to more than one of the types of listed conduct. See New Phoenix Sunrise Corp. v. Commissioner, 132 T.C. 161">132 T.C. 161, 132 T.C. 161">187 (2009), aff'd, 408 Fed. Appx. 908">408 Fed. Appx. 908 (6th Cir. 2010); sec. 1.6662-2(c), Income Tax Regs.

For purposes of section 6662, the term "negligence" includes any failure to make a reasonable attempt to comply with the provisions of the Code, and the term "disregard" includes any careless, reckless, or intentional disregard. Sec. 6662(c); see also Neely v. Commissioner, 85 T.C. 934">85 T.C. 934, 85 T.C. 934">947 (1985) (negligence is lack of due care or failure to do what a reasonably prudent person would do under the circumstances); sec. 1.6662-3, Income Tax Regs. Negligence also includes any failure to exercise ordinary and reasonable care in the preparation of a tax return or *325 any failure to keep adequate books and records and to properly substantiate items. Sec. 1.6662-3(b)(1), Income Tax Regs.

Petitioner claimed deductions for self-employed health insurance expenses for the years at issue. However, petitioner failed to substantiate that he had 2012 Tax Ct. Memo LEXIS 313">*326 health insurance coverage and that he paid for any health insurance. Failure to properly substantiate deductions constitutes negligence under section 6662(b)(1). See Cook v. Commissioner, T.C. Memo. 2012-167, 2012 Tax Ct. Memo LEXIS 167">2012 Tax Ct. Memo LEXIS 167, at *2012 Tax Ct. Memo LEXIS 167">8-*9; sec. 1.6662-3(b)(1), Income Tax Regs.

Petitioner also deducted personal expenses as business expenses. For example, petitioner reported nonpassive losses of $62,350 and $94,875 on Schedules E for the taxable years 2005 and 2006, respectively. These amounts, which were actually paid before the years at issue, related to litigation with petitioner's ex-wife and include attorney's fees, past due income support, and other payments to petitioner's ex-wife. Petitioner claimed that these amounts were "ordinary and necessary" business expenses under section 162. Petitioner's attempt to deduct personal expenses in contravention of the plain language of *326 section 262⁶ constitutes negligence. See WSB Liquidating Corp. v. Commissioner, T.C. Memo. 2001-9, 2001 Tax Ct. Memo LEXIS 9">2001 Tax Ct. Memo LEXIS 9, at *2001 Tax Ct. Memo LEXIS 9">23.

Petitioner claimed charitable contribution deductions on Schedules 2012 Tax Ct. Memo LEXIS 313">*327 C for amounts paid to political campaigns, despite section 162(e)(1)(B) explicitly disallowing such deductions. Petitioner's claiming of deductions that are explicitly disallowed by the Code constitutes negligence.

We find that respondent has met his burden of production with respect to negligence. Respondent introduced evidence that petitioner failed to properly substantiate deductions, deducted personal expenses, and failed to comply with the plain language of the Code.

There is a substantial understatement of income tax for any taxable year if the amount of the understatement for the taxable year exceeds the greater of 10% of the tax required to be shown on the return for the taxable year or $5,000. Sec. 6662(d)(1)(A). The understatements of income tax on petitioner's 2005 and 2006 Federal income tax returns are substantial. Respondent has met his burden of production with respect to petitioner's substantial understatements of income tax. The burden of proof remains with petitioner, and he has not met it. On the basis of *327 our holding that petitioner has failed to properly prosecute and is in default, we sustain respondent's determination regarding the accuracy-related penalties under 2012 Tax Ct. Memo LEXIS 313">*328 section 6662(a).

To reflect the foregoing,

Decision will be entered for respondent.