25 players were tied for playing the most seasons with 65+ losses, with 1 season. The first three are Isaiah Canaan, Hollis Thompson and Nik Stauskas.

most seasons with 65 losses by a player in their career
Interpreted as:
most seasons with 65 or more losses by a player in their career
CanaanThompsonStauskasGrantMcConnellSmithWigginsMiddletonBrewerFlynnLopezSessionsWilkinsWilliamsThompsonDavisChildressHarringtonTskitishviliJamisonOlowokandiEllisFortsonGarrettGoldwire1111111111111111111111111
NAMEGPSEASLMPGPPGRPGAPGSPGBPGTPGFGMFGAFG%3PM3PA3P%FTMFTAFT%MINPTSREBASTSTLBLKTOVPF+/-
Isaiah CanaanIsaiah Canaan7716725.511.02.31.80.70.21.23.49.436.02.36.336.31.92.383.31,966846174137561291133-484
Hollis ThompsonHollis Thompson7716728.09.83.51.30.50.31.03.58.839.71.95.138.00.91.271.92,15475827299362476187-370
Nik StauskasNik Stauskas7316524.88.52.51.90.60.31.32.97.538.51.54.532.61.21.677.11,809617183138442094115-403
Jerami GrantJerami Grant7716826.89.74.71.80.71.61.43.37.841.90.51.924.02.84.265.82,06674936113554127110215-491
T.J. McConnellT.J. McConnell8117119.86.13.14.51.20.11.72.75.747.00.41.134.80.30.563.41,6064932503679510140114-277
Jason SmithJason Smith8216521.88.04.01.70.40.51.33.17.243.40.20.535.71.51.983.01,7856563241403244104205-424
Andrew WigginsAndrew Wiggins8216636.216.94.62.11.00.62.26.113.943.70.51.531.04.35.776.02,9691,3873741708650177190-550
Khris MiddletonKhris Middleton8216730.012.13.82.11.00.21.54.610.444.01.53.541.41.41.786.12,4609903101698320123243-383
Corey BrewerCorey Brewer8216730.313.03.42.41.40.42.05.011.643.11.02.934.62.03.164.82,4821,06627919311729164224-509
Jonny FlynnJonny Flynn8116628.913.52.44.41.00.02.94.911.841.71.02.735.82.83.382.62,3391,09419135682223398-627
Brook LopezBrook Lopez8217036.918.88.62.30.71.72.56.913.849.90.00.00.05.16.281.73,0271,54270918755139204251-595
Ramon SessionsRamon Sessions8216721.18.22.63.10.70.11.73.16.845.60.00.26.72.02.871.71,732674214258555137137-215
Damien WilkinsDamien Wilkins8016619.85.63.11.70.80.31.02.14.843.30.20.829.51.31.679.81,585451249135662576144-276
Terrence WilliamsTerrence Williams7816822.68.44.52.90.60.11.63.38.340.10.41.331.01.31.871.51,7646563482234310124126-263
Jason ThompsonJason Thompson8216528.111.17.41.10.60.71.84.38.749.70.00.10.02.43.569.22,303910606934659146314-291
Ricky DavisRicky Davis8216736.113.84.33.41.10.22.35.111.843.31.64.140.51.92.478.72,9631,1303532768714191187-593
Josh ChildressJosh Childress8016829.710.16.01.90.90.41.33.88.047.00.20.723.22.42.982.32,3768074821517435106184-439
Junior HarringtonJunior Harrington8216524.45.13.03.41.00.21.92.15.736.20.10.325.00.91.465.22,0034182502778015157250-296
Nikoloz TskitishviliNikoloz Tskitishvili8116516.33.92.21.10.40.41.01.44.929.30.51.924.30.60.873.81,32031518191312984136-200
Antawn JamisonAntawn Jamison8216541.424.98.72.01.40.32.49.822.144.20.82.530.24.76.571.53,3942,04471516411428199225-554
Michael OlowokandiMichael Olowokandi8016631.29.88.20.50.41.82.24.19.543.70.00.01.52.465.12,4937836563835140177304-711
LaPhonso EllisLaPhonso Ellis7616533.914.37.22.80.90.62.35.413.340.70.82.628.42.73.480.52,5751,0835442136549173226-604
Danny FortsonDanny Fortson8016922.610.25.61.00.60.42.03.57.645.20.00.033.33.34.277.61,811816448764430157314-409
Dean GarrettDean Garrett8217132.17.37.91.10.71.61.03.06.942.80.00.01.42.164.82,632598644905713384197-756
Anthony GoldwireAnthony Goldwire8217127.09.21.83.41.00.11.03.37.842.30.82.038.41.82.380.62,21275114727786785149-522