United States v. Abel Mariano Jr. ( 1993 )


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  • February 2, 1993
    UNITED STATES COURT OF APPEALS
    For The First Circuit
    No. 92-1491
    UNITED STATES OF AMERICA,
    Appellee,
    v.
    ABEL A. MARIANO, JR.,
    Defendant, Appellant.
    No. 92-1630
    UNITED STATES OF AMERICA,
    Appellee,
    v.
    BARRY BUTTERWORTH,
    Defendant, Appellant.
    APPEALS FROM THE UNITED STATES DISTRICT COURT
    FOR THE DISTRICT OF RHODE ISLAND
    [Hon. Raymond J. Pettine, Senior U.S. District Judge]
    Before
    Selya, Circuit Judge,
    Bownes, Senior Circuit Judge,
    and Stahl, Circuit Judge.
    Richard  J. Shea, with whom Edward  C. Roy was on brief, for
    appellant Abel A. Mariano, Jr.
    Richard A. Gonnella for appellant Barry Butterworth.
    Edwin J.  Gale, Assistant United States  Attorney, with whom
    Lincoln  C.  Almond,  United  States Attorney,  and  Margaret  E.
    Curran,  Assistant United  States  Attorney, were  on brief,  for
    appellee.
    February 2, 1993
    SELYA,  Circuit  Judge.    These  consolidated  appeals
    SELYA,  Circuit  Judge.
    challenge  determinations made  by the  district court  under the
    federal sentencing  guidelines.  Concluding,  as we do,  that the
    court misconstrued  its authority to depart  from a predetermined
    sentencing  range in  consequence  of a  defendant's  substantial
    assistance,  U.S.S.G.      5K1.1  (Nov.  1991),   we  remand  for
    resentencing.
    I.  BACKGROUND
    The instant appeals find  their genesis in the polluted
    political purlieus of Pawtucket, Rhode Island.  See, e.g., United
    States  v.  Sarault,  
    975 F.2d 17
      (1st  Cir.  1992)  (affirming
    racketeering sentence  with respect  to Pawtucket's mayor).   The
    appellants, Abel  A. Mariano, Jr. and  Barry Butterworth, secured
    lucrative municipal  contracts and,  in the course  of performing
    the jobs,  lubricated the  wheels of  city  government by  paying
    under-the-table cash stipends  to insistent municipal  officials.
    Mariano  made periodic  payments  (perhaps totalling  as much  as
    $50,000) to forestall the  reassignment of sewer-line repair work
    to  another contractor.  Butterworth decided to play ball as part
    of  his effort to retain generous contracts for the renovation of
    McCoy Stadium.   In all, Butterworth made a series of payments to
    the ringleaders in an aggregate amount exceeding $100,000.
    Appellants' payments took place over a substantial span
    of time.  It  was only after the  authorities started to  uncover
    pervasive   corruption   in  the   Sarault   administration  that
    appellants  began cooperating  with the  U.S.  Attorney.   In the
    2
    aftermath of this cooperative effort, the government, rather than
    seeking indictments,  prepared informations charging the  two men
    with violating  18 U.S.C.    666(a)(2) (1988).1   The  defendants
    pled  guilty pursuant  to plea  agreements providing  in relevant
    part  that the government would pursue a reduction in the offense
    level  based on  the  defendants' assistance  to law  enforcement
    agencies.
    Mariano  and  Butterworth  were  charged  and sentenced
    separately.   In  each  instance, the  prosecution described  the
    defendant's  cooperation  and  argued  for a  six-level  downward
    departure  pursuant to  U.S.S.G.    5K1.1.    The district  court
    refused to depart and sentenced each defendant to  a twenty-seven
    month  prison term   an incarcerative sentence  at the top end of
    the guideline sentencing range (GSR).   The government moved  for
    reconsideration.   In explaining  his refusal to  reconsider, the
    district judge, referring  to and quoting  from United States  v.
    Aguilar-Pena,  
    887 F.2d 347
     (1st  Cir. 1989), stated  that he did
    not have discretion to depart.
    In these appeals,2 appellants  claim in unison that the
    1The  statute of conviction criminalizes "corruptly giv[ing]
    . . .  anything of value to any person,  with intent to influence
    or reward an agent of . . . local . . . government, or any agency
    thereof, in connection with  any business, transaction, or series
    of transactions . . . involving  [$5000 or more]," so long as the
    governmental  unit  in  question  receives   substantial  federal
    subsidies.  18 U.S.C.   666(a)(2).
    2Although the plea agreements  contain provisions by  virtue
    of which the defendants ostensibly waived their rights of appeal,
    the  government has conceded that, in  the circumstances of these
    cases,  the waiver  provisions are  impuissant.   We  accept this
    concession  uncritically.  Hence, we  take no view  of either the
    3
    district court erred in establishing the base offense level (and,
    hence,  in fixing  the GSR),  that the  court misapprehended  the
    legal standard governing departures under section 5K1.1, and that
    their sentences  were "plainly unreasonable" in  derogation of 18
    U.S.C.   3742(a)(4) (1988).   In addition, Mariano contends  that
    the   district   court    labored   under   fundamental   factual
    misconceptions and  violated the  Due Process Clause  by focusing
    exclusively  on  deterrence  concerns  to  the  detriment  of  an
    individualized sentence.  Not to be outdone, Butterworth contends
    that  the government  breached the plea  agreement by  failing to
    argue enthusiastically enough in support of a downward departure.
    We concentrate initially  on appellants' flagship claim
    the   assertion  that  the  court   below  misapprehended  the
    controlling legal  standard, thus mismeasuring the  limits of the
    discretion entrusted to  it under  section 5K1.1.   We take  this
    tack because, if this  claim pans out, most of  appellants' other
    asseverations need not be considered.
    II.  THE COURT'S AUTHORITY TO DEPART
    We  begin our  discussion of  the court's  authority to
    depart  by pondering  a jurisdictional  quandary.   That quandary
    resolved, we then address the merits of appellants' claim.
    A.  Appellate Jurisdiction.
    Ordinarily,  an appeal  will  not lie  from a  district
    court's refusal  to depart from a  properly calculated sentencing
    enforceability  vel non of  such waivers or  the safeguards which
    must be employed in respect thereto.
    4
    range.  See United  States v. Tardiff,  
    969 F.2d 1283
    , 1290  (1st
    Cir. 1992); United States  v. Romolo, 
    937 F.2d 20
    , 22 (1st  Cir.
    1991) (collecting cases).   However,  appellate jurisdiction  may
    attach  when it appears that  the failure to  depart stemmed from
    the  sentencing court's  mistaken impression  that it  lacked the
    legal  authority  to  depart  or,  relatedly,  from  the  court's
    misapprehension  of the  rules governing  departure.   See United
    States v. Amparo, 
    961 F.2d 288
    , 292 (1st Cir.), cert. denied, 
    113 S. Ct. 224
      (1992); United States  v. Lauzon, 
    938 F.2d 326
    ,  330
    (1st Cir.), cert. denied, 
    112 S. Ct. 450
     (1991); Romolo, 
    937 F.2d at 22
    .   Although this  paradigm is  dictated by  the Sentencing
    Reform Act, see Romolo,  
    937 F.2d at 23
     (discussing  operation of
    18  U.S.C.     3742(a)), it  also  works  well  from a  practical
    standpoint:   in respect  to declinations to  depart, the limited
    appellate review that is available serves to correct errors which
    are   essentially  "legal"   in  nature,   but  does   not  brook
    interference with a  sentencing court's  exercise of  factfinding
    functions or discretion.  See  Amparo, 961 F.2d at 292;  see also
    Romolo, 
    937 F.2d at 23
    .
    These  appeals fit  snugly within  the contours  of the
    exception  permitting   appellate  review.     The  gravamen   of
    appellants'  complaint   is  their  colorable  claim3   that  the
    3In what it terms "the rarest of all cases," the government,
    which has  a duty to see  that justice is done,  Berger v. United
    States,  
    295 U.S. 78
    ,  88 (1935),  argues  that the  defendants'
    assignment of legal error is  on the mark.  While such  unanimity
    of  purpose might raise jurisdictional concerns  in a civil case,
    see  Muskrat  v.   United  States,  
    219 U.S. 346
    ,   361  (1911)
    (explaining adversity requirement); see  also Moore v. Charlotte-
    5
    district court  confused the legal standard  governing departures
    under  U.S.S.G.     5K1.1   with  the  legal  standard  governing
    departures  under  a  markedly  different guideline,  U.S.S.G.
    5K2.0.   This claim  presents a  question  of law,  not of  fact,
    comfortably  within our  assigned purview.   We  hold, therefore,
    that we have jurisdiction over these appeals.
    B.  The Distinction Between Departure Modalities.
    We turn next  to the merits of the claim.   Because the
    assignment of error involves the parameters of a district judge's
    departure authority,  we afford plenary review.   See Lauzon, 938
    F.2d at 330; cf. United States v. Diaz-Villafane, 
    874 F.2d 43
    , 49
    (1st Cir.) (holding  that de  novo review is  warranted when  the
    court  of appeals  is called  upon to  determine "whether  or not
    circumstances are of a  kind or degree that may  appropriately be
    relied  upon to  justify departure"  under section  5K2.0), cert.
    denied, 
    493 U.S. 862
     (1989).
    The district judge explicitly interpreted  our decision
    in United States v.  Aguilar-Pena, 
    887 F.2d 347
     (1st  Cir. 1989),
    as  restricting his  ability to depart  downward in  these cases.
    Aguilar-Pena,  however, involved  a district court's  decision to
    Mecklenburg Bd. of  Educ., 
    402 U.S. 47
    , 48  (1971) (per  curiam)
    (finding  no case  or  controversy where  "both litigants  desire
    precisely the  same result"), criminal  cases are a  breed apart.
    When  the government  confesses error  in a  criminal proceeding,
    appellate   courts  routinely  continue  to  exercise  previously
    acquired jurisdiction.  See, e.g., Mariscal v. United States, 
    449 U.S. 405
     (1981) (per curiam);  Young v. United  States, 
    315 U.S. 257
    , 258-59 (1942); see also United States v. Udo, 
    963 F.2d 1318
    ,
    1319 (9th Cir. 1992) (reviewing a failure to depart pursuant to
    5K1.1  in  circumstances analogous  to  those  presented in  this
    case).
    6
    depart under section  5K2.0.4  See id. at  349-53.  Under section
    5K2.0, a district court  is empowered to depart  from the GSR  if
    there  "exists an  aggravating  or mitigating  circumstance of  a
    kind,  or to a degree, not adequately taken into consideration by
    the Sentencing Commission."  U.S.S.G.   5K2.0  (quoting 18 U.S.C.
    3553(b)).  Noting that "the birth of the Sentencing Commission
    was  to  some extent  reflective of  Congress's ardent  desire to
    dispense   with  inequalities   based  on   localized  sentencing
    responses,"  Aguilar-Pena, 
    887 F.2d at 352
    ,  we  held that  the
    district  court's authority  to  depart under  section 5K2.0  was
    restricted  to  those few  instances  where  there is  "something
    'special' about  a given offender,  or the  accouterments of  the
    crime committed,  which distinguishes the case  from the mine-run
    for  that offense."   
    Id. at 350
    .   In  other words, Aguilar-Pena
    reflected this court's staunch belief that section 5K2.0 operates
    as  a safety  valve  to  be employed  at  the  discretion of  the
    district judge on those infrequent occasions when some important,
    atypical  factor,   not   duly  considered   by  the   Sentencing
    Commission, removes  a particular case from "the  heartland for a
    given offense."  
    Id. at 351
    .
    U.S.S.G.     5K1.1  is  a different  provision  with  a
    different  raison d'etre.    Congress  specifically directed  the
    Sentencing Commission to
    4Aguilar-Pena flowed  naturally from,  and relied upon,  our
    opinion in United States v. Diaz-Villafane.   See, e.g., Aguilar-
    Pena, 
    887 F.2d at
    349-50 (citing and quoting  Diaz-Villafane, 874
    F.2d  at 49-52).   Like  Aguilar-Pena, Diaz-Villafane  involved a
    departure under U.S.S.G.   5K2.0.
    7
    assure  that  the   guidelines  reflect   the
    general appropriateness of  imposing a  lower
    sentence than would otherwise  be imposed . .
    .   to  take   into  account   a  defendant's
    substantial  assistance in  the investigation
    or  prosecution  of  another  person  who has
    committed an offense.
    28  U.S.C.    994(n) (1988).   Section  5K1.1 sprouted  from this
    statutory seed.  It provides, inter alia, that:
    Upon  motion of  the government  stating that
    the   defendant   has  provided   substantial
    assistance    in    the   investigation    or
    prosecution   of   another  person   who  has
    committed  an offense,  the court  may depart
    from the guidelines.
    U.S.S.G.    5K1.1.   This  guideline serves  a dual purpose.   In
    addition to permitting ex post tailoring of defendants' sentences
    to reflect  meaningful assistance  rendered between the  dates of
    apprehension and  sentencing, it  provides  defendants, ex  ante,
    with an incentive to cooperate in the  administration of justice.
    See, e.g., United States v. Damer, 
    910 F.2d 1239
    , 1241 (5th Cir.)
    (per curiam), cert. denied, 
    111 S. Ct. 535
     (1990).
    The  methodological contrast between  the two departure
    modalities is glaring.  Because section 5K2.0 in a sense operates
    to  promote  disparity,  the  Sentencing  Commission  strove   to
    minimize the  number of times it would  be invoked.  But, because
    section  5K1.1  operates  in  part  as  an  incentive,  promoting
    cooperation  with  law   enforcement  agencies,  the   Sentencing
    Commission strove to  maximize the  number of times  it would  be
    invoked.5      These  divergent   purposes,   coupled   with  the
    5Available  statistics reflect  the Commission's  success in
    achieving this differential.   Of 31,785 dispositions reported in
    1991,  11.9  percent involved  substantial  assistance departures
    8
    significant  linguistic differences  between the  two guidelines,
    clearly  indicate that  the legal  standard for  departures under
    section  5K2.0  cannot  be  transplanted   into  the  substantial
    assistance  sphere.  The district  court, therefore, erred in its
    stated reliance on Aguilar-Pena.
    C.  The Standard for Substantial Assistance Departures.
    In  order to  determine whether  the court's  error was
    harmless,  we must explore  the dimensions of  the legal standard
    that the  district court should have  used.  We have  not yet had
    occasion to discuss the way in which departure decisions ought to
    be made under U.S.S.G.   5K1.1.  We do so today.
    1.       Discretion.      We    begin   with   bedrock.
    1.       Discretion.
    Notwithstanding  that a government motion is a  sine qua non to a
    departure for  a defendant's substantial assistance,  see Wade v.
    United States, 
    112 S. Ct. 1840
    , 1843 (1992), the decision whether
    to depart after  the government has made such a  motion, like the
    related decision  as to  the extent of  any resultant  departure,
    falls squarely within the district  court's domain.  The district
    court  is not  obligated  to  depart  downward simply  because  a
    grateful  prosecutor  prefers a  lighter  sentence.   See  United
    States v. Spiropoulos, 
    976 F.2d 155
    , 162 (3d Cir.  1992); United
    States v. Ah-Kai, 
    951 F.2d 490
    , 494 (2d Cir. 1991); United States
    v. Munoz, 
    946 F.2d 729
    , 730 (10th  Cir. 1991); United States  v.
    Carnes, 
    945 F.2d 1013
    , 1014  (8th Cir. 1991);  United States  v.
    whereas only 7.5 percent  involved all other departures combined.
    See 1991 United States Sentencing Commission Ann. Rep. at 133-35.
    9
    Richardson,  
    939 F.2d 135
    , 139  (4th Cir.), cert.  denied, 
    112 S. Ct. 599
     (1991), 
    112 S. Ct. 942
     (1992);  United States v.  Keene,
    
    933 F.2d 711
    ,  715 (9th  Cir. 1991);  Damer, 910  F.2d at  1241;
    United  States v. Pippin, 
    903 F.2d 1478
    , 1485  (11th Cir. 1990).
    Put   bluntly,  while   a  government   motion  is   a  necessary
    precondition  to  a downward  departure  based  on a  defendant's
    substantial assistance, the docketing  of such a motion  does not
    bind a  sentencing court  to abdicate its  responsibility, stifle
    its independent judgment, or comply blindly with the prosecutor's
    wishes.
    The government,  seeking a  more prominent role  in the
    decisionmaking process,  points out the  Commission's advice that
    "[s]ubstantial   weight  should  be  given  to  the  government's
    evaluation  of   the  extent   of  the  defendant's   assistance,
    particularly  where the  extent and  value of the  assistance are
    difficult to ascertain."  U.S.S.G.   5K1.1, comment. (n.3).  But,
    this  advice, although sound, was  never intended to  rein in the
    district court's  discretion concerning the need  for, and extent
    of,  a  downward departure  once a  government  motion is  on the
    table.  See  United States  v. Castellanos, 
    904 F.2d 1490
    ,  1497
    (11th  Cir. 1990).   Rather,  Application Note  3 sets  forth the
    suggested  degree of  deference that  should be  afforded  to the
    prosecution's assessment  of the facts surrounding  a defendant's
    assistance and intimates  that, particularly in difficult  cases,
    the sentencing court ought  not to "inquire too  intrusively into
    the government's  file" on  this delicate subject.   Spiropoulos,
    10
    
    976 F.2d at
    163 n.5; see also  Keene, 
    933 F.2d at 714
     (observing
    that the "prosecutor is  in the best position to know whether the
    defendant's cooperation has been helpful").  When all is said and
    done,  it  remains  the  district  judge's  decision     not  the
    prosecutor's   whether to depart, and if so, to what degree.
    2.   Relevant Factors.   Although the  district court's
    2.   Relevant Factors.
    discretion in  passing upon a section 5K1.1 motion is wide, it is
    not unbridled.  The guideline itself provides that:
    The appropriate reduction shall be determined
    by  the  court for  reasons  stated that  may
    include,    but    are   not    limited   to,
    consideration of the following:
    (1)  the  court's   evaluation  of   the
    significance    and    usefulness   of    the
    defendant's    assistance,     taking    into
    consideration the  government's evaluation of
    the assistance rendered;
    (2) the  truthfulness, completeness, and
    reliability of any  information or  testimony
    provided by the defendant;
    (3)  the   nature  and  extent   of  the
    defendant's assistance;
    (4) any injury  suffered, or any  danger
    or  risk of  injury to  the defendant  or his
    family resulting from his assistance;
    (5)  the  timeliness of  the defendant's
    assistance.
    U.S.S.G. 5K1.1.   While  the Commission's list  is representative
    rather  than exclusive,  the  five enumerated  factors should  be
    considered the mother lode  of substantial assistance  inquiries.
    A district court,  faced with a section  5K1.1 motion, must at  a
    bare  minimum indicate its cognizance  of these factors.   In the
    typical  case the  court  would also  do  well to  make  specific
    findings regarding each item.
    The open-ended  nature of  the statutory list  does not
    11
    mean that a district court may consider any datum it pleases when
    passing upon a section 5K1.1 motion.  As a basis for departing, a
    court may  consider mitigating factors  only to  the extent  that
    they  can  fairly be  said to  touch  upon the  degree, efficacy,
    timeliness,  and  circumstances  of  a  defendant's cooperation.6
    See United States  v. Chestna,  
    962 F.2d 103
    ,  106-07 (1st  Cir.)
    (per  curiam), cert. denied, 
    113 S. Ct. 334
     (1992); United States
    v. Thomas, 
    930 F.2d 526
    , 528-29  (7th Cir.), cert. denied, 
    112 S. Ct. 171
     (1991).  After  all, the substantial assistance provision
    is not to be used as a mechanism for short-circuiting other, more
    restrictive provisions of the  sentencing guidelines.  See United
    States v. Hall, 
    977 F.2d 861
    , 865 (4th Cir. 1992).7
    A  somewhat different  situation obtains in  respect to
    the factors  that  a court  may  consider as  a means  to  remain
    within,  or   incrementally  closer  to,  the  GSR.    Since  the
    sentencing range itself  is an expression  of Congress's will,  a
    district  court  retains  broad  discretion   to  exhume  factors
    unrelated to substantial assistance before burying the GSR.  See,
    e.g.,  United States  v. Mittelstadt, 
    969 F.2d 335
    ,  336-37 (7th
    6The narrowing effect of  this circumscription should not be
    exaggerated.     The  factors  that  legitimately   relate  to  a
    defendant's cooperation may be  many and varied.  See  U.S.S.G.
    5K1.1, comment. (backg'd) ("The  nature, extent, and significance
    of assistance can involve  a broad spectrum of conduct  that must
    be evaluated by the court on an individual basis.").
    7As  this   logic  makes  clear,  the   government  and  the
    appellants are incorrect in suggesting here that a district court
    is  obliged  to consider  factors  such  as proportionality  when
    deciding whether,  or how much,  to depart  under section  5K1.1.
    See United  States v. Kohl,  
    972 F.2d 294
    ,  299 (9th Cir.  1992);
    Richardson, 939 F.2d at 139.
    12
    Cir.  1992) (ruling  that the  district court  did not  abuse its
    discretion  in considering  defendant's chronic  alcoholism on  a
    section 5K1.1 motion); Carnes, 
    945 F.2d at 1014
     (holding that the
    benefit a defendant received  from the prosecution's decision not
    to  press  an  additional  charge was  a  permissible  ground for
    limiting  the extent of a downward  departure).  Even if the five
    factors enumerated in section 5K1.1 weigh in a defendant's favor,
    the district court may, on the basis of other considerations, not
    constitutionally proscribed, cf., e.g., Wade, 
    112 S. Ct. at
    1843-
    44;  United States  v. Drown,  
    942 F.2d 55
    , 60 (1st  Cir. 1991),
    decide to forgo  or curtail a downward  departure for substantial
    assistance.
    In   sum,   the   limitations   on   the   variety   of
    considerations that a court may mull in withholding or curtailing
    a substantial assistance departure are not nearly so stringent as
    those which pertain when a court  in fact departs downward.  This
    seeming  paradox is neither unusual nor unsettling; indeed, it is
    this very  quality of unequal centrifugal  and centripetal forces
    that  helps distinguish  discretionary departure  provisions like
    section 5K1.1 from the  sentencing guidelines' array of mandatory
    adjustment  provisions like  U.S.S.G.     3E1.1  (adjustment  for
    acceptance  of  responsibility)  and  U.S.S.G.      3B1.1,  3B1.2
    (adjustment for aggravating or mitigating role in the offense).
    3.   Weighing the Factors.  Once the government files a
    3.   Weighing the Factors.
    section 5K1.1 motion, weighing  the relevant factors in  order to
    decide  whether to depart (and  if so, by  how much) is something
    13
    best  done by the sentencing  court.  United  States v. Atkinson,
    F.2d     ,     (7th Cir. 1992) [
    1992 U.S. App. LEXIS 30082
     at
    *22-25]; Thomas, 930 F.2d at  531.  In the section 5K1.1  milieu,
    as elsewhere,  the court of  appeals will, to  the extent of  its
    jurisdiction, review  discretionary decisions only  for abuse  of
    discretion; and we will review the extent of a departure based on
    an  acceptable set of factors only to ensure reasonableness.  See
    Diaz-Villafane, 874 F.2d at 49.
    D.  Summing Up.
    We rule today that the legal standard for departure  is
    materially different under U.S.S.G.   5K1.1 than under U.S.S.G.
    5K2.0.   A district court confronted with a government motion for
    departure  pursuant to  section 5K1.1  must consider  the factors
    specifically  enumerated  in  that  guideline as  well  as  other
    factors which in the  court's judgment bear on the  decision.  In
    so  doing,  however, the  court  must  recognize that  mitigating
    concerns  are  relevant   only  insofar  as  they  relate   to  a
    defendant's substantial assistance.   In all events, the district
    court retains wide discretion  concerning whether to depart under
    section  5K1.1; and, if it decides that a departure is warranted,
    it also possesses appreciable discretion in fixing the  extent of
    the departure.
    In  these  cases,  the   district  court  premised  its
    decision  not  to depart  on a  legal  standard designed  to hold
    departures  to a minimum    a standard  that has  no relevance in
    respect to substantial assistance departures.  And, although many
    14
    of the integers that enter into the section 5K2.0 calculus can be
    considered  for  certain purposes  under  section  5K1.1, we  are
    unable confidently to say  on this record that the  judge's error
    was  harmless.    Thus, we  remand  to  the  district court  with
    instructions  to vacate  appellants'  sentences and  conduct  new
    sentencing hearings.  We see no need to require  that a different
    judge preside over  the resumed proceedings.   Cf., e.g.,  United
    States v. Diaz-Bastardo, 
    929 F.2d 798
    , 800-01 (1st Cir. 1991).
    III.  THE COURT'S CHOICE OF AN ANALOGOUS GUIDELINE
    Given  the fact  that new  sentencing hearings  will be
    held,  we decline,  with  one exception,  to address  appellants'
    other  challenges  to  the  proceedings below.8    The  exception
    relates  to   appellants'  assertion  that  the  district  court,
    confronted by  a lacuna  in the  guidelines,  failed properly  to
    select  the  most analogous  guideline  as a  starting  point for
    computing  the GSR.  We treat  with this assertion because we can
    envision no circumstances in  which a choice of this  nature will
    not face the district court on remand.
    We set the stage.  The Sentencing Commission has yet to
    promulgate  an   offense  guideline   covering  the  offense   of
    conviction  in these cases, i.e.,  the making of illicit payments
    to  a municipal official in  violation of 18  U.S.C.   666(a)(2).
    In  such circumstances,  U.S.S.G.    2X5.1  directs the  district
    8Because  we  do   not  reach  appellants'  "reasonableness"
    argument, we  take no  view of  the  suitability vel  non of  the
    sentences originally imposed.
    15
    court to  "apply the most analogous offense  guideline" unless no
    "sufficiently  analogous guideline"  can be  found.9   Appellants
    urged that U.S.S.G.   2C1.2 (dealing in part with the giving of a
    gratuity  to a  public official)  provided the  best basis  for a
    comparison.   The  district court  rejected this  exhortation and
    found U.S.S.G.    2C1.1 (dealing  with bribery of,  and extortion
    by, public officials) to be the most analogous guideline.
    We  discern no  error  in this  determination.   Before
    explaining  our   reasoning,  however,   we  first   address  the
    appropriate standard of appellate review.
    A.  Standard of Review.
    An appellate  tribunal must "give due  deference to the
    district court's application of the guidelines to the facts."  18
    U.S.C.   3742(e)  (1988).   We have interpreted  this statute  as
    requiring,  in most instances, that the court of appeals review a
    trial court's application of a sentencing  guideline to the facts
    only for clear error.  See, e.g., United States v. Ruiz, 
    905 F.2d 499
    , 507  (1st Cir. 1990); United States v. Wright, 
    873 F.2d 437
    ,
    444  (1st Cir.  1989).    The  propriety  of  using  the  clearly
    erroneous  standard   in   scrutinizing  a   sentencing   court's
    9In  the court  below, appellants  argued that  a particular
    offense guideline,  U.S.S.G.     2C1.2, was  a  better  fit  than
    U.S.S.G.   2C1.1 (the offense guideline deemed most comparable by
    the  district judge).   On appeal,  Butterworth attempts  for the
    first  time   to  raise  the  different  issue   of  whether  any
    sufficiently analogous guideline exists.  This issue has not been
    properly preserved  for appellate review.   See United  States v.
    Slade,     F.2d    ,      (1st Cir. 1992) [No. 92-1176, slip  op.
    at 6] (reiterating the established rule that points not argued in
    the  district  court  cannot be  raised  for  the  first time  on
    appeal).
    16
    application of law  to fact  will depend largely  on whether  the
    question presented  is essentially factual or  essentially legal;
    the  more fact-dominated the question, the more likely it is that
    clear-error review  will be  appropriate.   See United States  v.
    Ortiz,  
    878 F.2d 125
    , 126-27  (3d Cir.  1989); United  States v.
    Daughtrey,  
    874 F.2d 213
    , 217-18 (4th Cir. 1989); see also Roland
    M. v.  Concord School Comm., 
    910 F.2d 983
    , 990-91 (1st Cir. 1990)
    (discussing desirability of clear-error review in instances where
    a district court must find the facts and then make  an evaluative
    judgment, applying a defined legal standard to the facts),  cert.
    denied, 
    111 S. Ct. 1122
     (1991).
    In  these cases, a series of  factors suggests that the
    contested  issue lies  closer to  the fact-intensive  end  of the
    continuum:    there  is  no indication  that  the  district court
    misunderstood the  choices presented under the  guidelines; there
    is  no  articulation of  a dispute  concerning  the reach  of the
    provisions  proffered  as  suitable  analogs;  and  there  is  no
    necessity for us, in resolving  the controversy, to determine the
    far  broader  (and  essentially  legal)  question  of  whether  a
    particular offense guideline will always  be most analogous to 18
    U.S.C.   666(a)(2).  Simply stated, the issue before the district
    court  was whether  appellants' actions  in "corruptly  giv[ing]"
    payoffs  to  municipal officials  "with  intent  to influence  or
    reward"  those officials  in connection  with city  contracts, 18
    U.S.C.     666(a)(2), were  more  akin to  providing  a gratuity,
    U.S.S.G.    2C1.2,  than to  passing a  bribe, U.S.S.G.    2C1.1.
    17
    This issue is  essentially factual.   It required  the court,  in
    effect,  to  find  the  facts   pertaining  to  the  offenses  of
    conviction and make  evaluative judgments concerning those  facts
    (including  a judgment  as to  whether appellants'  payments were
    intended to  "influence," rather than  "reward," city officials).
    Accordingly,   we  apply   the  clearly  erroneous   standard  of
    review.10
    B.  The Appropriate Analogy.
    The essential difference between a bribe and an illegal
    gratuity is the intention of the bribe-giver to effect a quid pro
    quo.  See United States  v. Muldoon, 
    931 F.2d 282
    , 287  (4th Cir.
    1991).  Hence, a bribery guideline, section 2C1.1, applies when a
    transfer  of money  has "a  corrupt purpose,  such as  inducing a
    public official to  participate in  a fraud or  to influence  his
    official actions."   U.S.S.G.    2C1.1, comment. (backg'd).   The
    gratuity provision, on the other hand, does not include a corrupt
    purpose as  an element of  the offense.   See  U.S.S.G.    2C1.2,
    comment. (backg'd).
    10In the event  no sufficiently analogous  guideline exists,
    the  sentencing  court  must  resort to  the  general  principles
    adumbrated  in 18 U.S.C.   3553(b) (1988) (providing that, in the
    absence  of  an offense  guideline,  the  court  shall impose  an
    "appropriate" sentence,  having due  regard for, inter  alia, the
    gravity  of the  offense;  the need  for punishment,  deterrence,
    retraining, and the like; and  "the relationship of the  sentence
    imposed to sentences prescribed  by [other] guidelines . .  . and
    the applicable policy statements of  the Sentencing Commission").
    Because that scenario  has no bearing here, see supra  note 9, we
    find inapposite the standard of review limned in United States v.
    Gabay,  
    923 F.2d 1536
    , 1545  (11th Cir. 1991)  (employing de novo
    review where  defendant contended that  no sufficiently analogous
    guideline existed).
    18
    This distinction between the  two offense guidelines is
    brought into bold relief by  the differences between the statutes
    to  which the guidelines relate.   The bribery guideline applies,
    for example, to the offense of "corruptly giv[ing] . . . anything
    of value" to a federal official with the intent of "influenc[ing]
    any  official act" or "inducing"  the official to  violate his or
    her  lawful duty.   18  U.S.C.    201(b)(1)  (1988).   This seems
    virtually  to mirror the statute of conviction here, which, among
    other things, criminalizes "corruptly giv[ing]  . . . anything of
    value  to any  person, with  intent to  influence" a  decision of
    state or local  government.  18 U.S.C.    666(a)(2).  The  common
    thread  that  runs through  both statutes  is  the intent  of the
    payer, by the greasing  of palms, to affect the future actions of
    a public official.  In contrast, the gratuity guideline refers to
    crimes of a somewhat  different genre.  It applies,  for example,
    to persons who  give things of value to federal  officers "for or
    because of any official act performed or to be  performed by such
    public official."   18  U.S.C.    201(c)(1)(A) (1988).   Notably,
    under the gratuity  guideline, there is  no requirement that  the
    gift be "corruptly" given  with the intent to affect  the payee's
    mindset or actions.  Phrased another way, the  gratuity guideline
    presumes a situation in which the offender gives the gift without
    attaching any  strings,  intending it  instead  as a  reward  for
    actions  the public  official  has already  taken  or is  already
    committed to take.
    With these distinctions in mind, appellants' contention
    19
    is easily dispelled.   Here, Mariano admitted that he  paid large
    sums  of  money  in  order   to  forestall  city  officials  from
    reassigning  the work.    Butterworth likewise  admitted that  he
    forked  over $100,000 so that  he could retain valuable contracts
    which Pawtucket might otherwise  have redirected to a competitor.
    Since Mariano and Butterworth  each sought to receive a  quid pro
    quo, in the form  of future (favorable) treatment, and  since the
    offenses to  which they  pleaded guilty involved  corrupt intent,
    the district  court's determination that their  actions were more
    akin  to  bribe-giving  than   to  gift-giving  was  not  clearly
    erroneous.
    To be sure, appellants  protest that they were victims,
    not  perpetrators,  of  an  extortionate scheme,  and  that  they
    received nothing extra in  return for their magnanimity.   We are
    unmoved  by these  plaints.   The fact  that appellants,  in some
    sense, may have  been the quarry of a pack  of venal politicians,
    and did not themselves  initiate the forbidden transactions, does
    not negate  the district court's  choice of a  guideline analogy.
    Bribery and extortion are not mutually exclusive concepts.   See,
    e.g.,  United States v. Hathaway,  
    534 F.2d 386
    ,  395 (1st Cir.),
    cert. denied, 
    429 U.S. 819
     (1976).  And the fact that appellants
    had already  received sewer-line and stadium  repair contracts at
    payoff time  is  also not  outcome  determinative.   Despite  the
    chronology,  the  district  court  could  supportably  find  that
    Mariano and Butterworth corruptly intended their illicit payments
    to influence the  future actions of the late,  unlamented Sarault
    20
    administration.
    We  need go no further.   Having willingly  sat down to
    sup  with the devil, appellants  cannot now expect  the courts to
    swallow their tale uncritically.  The guideline analogy chosen by
    the  district  court was  well within  its  purview.   See United
    States v.  St. Cyr, 
    977 F.2d 698
    , 706  (1st Cir.  1992) (holding
    that  "when  there are  two plausible  views  of the  record, the
    sentencing  court's adoption of  one such view  cannot be clearly
    erroneous"); Ruiz, 
    905 F.2d at 508
     (similar).
    The defendants' sentences are vacated and the cases are
    remanded for resentencing.
    21