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I tried leak2.py with valgrind, I've uncommented the lines you mentioned.
> $ valgrind python3 leak2.py 
==28421== Memcheck, a memory error detector
==28421== Copyright (C) 2002-2013, and GNU GPL'd, by Julian Seward et al.
==28421== Using Valgrind-3.10.1 and LibVEX; rerun with -h for copyright info
==28421== Command: python3 leak2.py
==28421=わ=わ 
=わ=わ28421=わ=わ 
=わ=わ28421== HEAP SUMMARY:
==28421== in use at exit: 1,599,354 bytes in 11,594 blocks
==28421== total heap usage: 284,971 allocs, 273,377 frees, 37,976,898 bytes allocated
==28421== 
==28421== LEAK SUMMARY:
==28421== definitely lost: 0 bytes in 0 blocks
==28421== indirectly lost: 0 bytes in 0 blocks
==28421== possibly lost: 597,482 bytes in 2,319 blocks
==28421== still reachable: 1,001,872 bytes in 9,275 blocks
==28421== suppressed: 0 bytes in 0 blocks
==28421== Rerun with --leak-check=full to see details of leaked memory
==28421== 
==28421== For counts of detected and suppressed errors, rerun with: -v
==28421== ERROR SUMMARY: 0 errors from 0 contexts (suppressed: 0 from 0)
I've removed `import readline` from leak2.py, everything else left as in previous run (also ofc removed tracemalloc).
> $ valgrind python3 leak3.py 
==28515== Memcheck, a memory error detector
==28515== Copyright (C) 2002-2013, and GNU GPL'd, by Julian Seward et al.
==28515== Using Valgrind-3.10.1 and LibVEX; rerun with -h for copyright info
==28515== Command: python3 leak2.py
==28515=わ=わ 
=わ=わ28515=わ=わ 
=わ=わ28515== HEAP SUMMARY:
==28515== in use at exit: 1,599,384 bytes in 11,595 blocks
==28515== total heap usage: 285,648 allocs, 274,053 frees, 38,126,379 bytes allocated
==28515== 
==28515== LEAK SUMMARY:
==28515== definitely lost: 30 bytes in 1 blocks
==28515== indirectly lost: 0 bytes in 0 blocks
==28515== possibly lost: 597,375 bytes in 2,317 blocks
==28515== still reachable: 1,001,979 bytes in 9,277 blocks
==28515== suppressed: 0 bytes in 0 blocks
==28515== Rerun with --leak-check=full to see details of leaked memory
==28515== 
==28515== For counts of detected and suppressed errors, rerun with: -v
==28515== ERROR SUMMARY: 0 errors from 0 contexts (suppressed: 0 from 0)
Duh? Why does readline have this effect?