Lost all money he had earned till 1990 by lending it to a friend.

Astrological Magazine Mar 2003 p#47.
lost at the end 2000.

Jupiter dasa Rahu bukthi during end of 2000.

Ju  S(2,5,8) in Rahu*(2,3,11).
No one is in Ju star. So Ju is also strong S(2,5,8).

Ju is subjected to papakartari.

Rahu S(2,3,11) in MarsR* (4,9)

During end of 2000, Transit is as follows:

Date of Birth:         November 21, 2000
Time of Birth:         6:29:11 pm
Time Zone of Birth:    5:30 East of GMT
Longitude of Birth:    77 E 32
Latitude of Birth:     12 N 52
Lunar month (maasa):   Karthika
Lunar day (tithi):     Krishna Ekadasi
Tithi balance:         0.4275
Nakshatra balance:     0.8098
Sun-Moon Yoga:         Priti
Sun-Moon Karana:       Balava
Vara (weekday):        Tuesday

Sunrise = 6:21 am (Apparent rise - upper limb)
Ayanamsa = 23-51-54
Dasa year length chosen = 365.2425 days

Planet      Position  Pada        CharaK

Ascdt       16 Ta 13  Rohini 2       -
Sun          5 Sc 40  Anuradha 1     GK
Moon        12 Vi 32  Hastha 1      PiK
Mars        16 Vi 51  Hastha 3      AmK
Mercury     17 Li 48  Swathi 4       AK
Jupiter (R) 13 Ta 10  Rohini 1       MK
Venus       16 Sg 14  Poo.Shaa. 1    BK
Saturn (R)   3 Ta 27  Krittika 3     DK
Rahu        23 Ge 57  Punarvasu 2    PK
Ketu        23 Sg 57  Poo.Shaa. 4    -

JuR Tr 12L* and Rh Tr Ju*(2,5,8).

Rh S(11=Friend), 5,8,12 => loss.

If Ju would have been direct (who is not only DL is also star transited by BL), native would have recovered money.

Conclusion : Do not lend money if DL, BL are S(5,8,12), transiting the star of S(5,8,12) and either they or transmitted star lord is retrograde.