Para podermos utilizar o Glide com conexções Https será necessário adcionarmos essas duas dependências no no projeto e criar duas classes.

Depencdências

implementation 'com.github.bumptech.glide:annotations:4.5.0'
kapt 'com.github.bumptech.glide:compiler:4.5.0'

Classes

@GlideModule
public class MyGlideModule extends AppGlideModule {

    @Override
    public void applyOptions(Context context, GlideBuilder builder) {
        super.applyOptions(context, builder);
    }

    @Override
    public void registerComponents(@NonNull Context context, @NonNull Glide glide, @NonNull Registry registry) {
        OkHttpClient okHttpClient= UnsafeOkHttpClient.getUnsafeOkHttpClient();
        registry.replace(GlideUrl.class, InputStream.class, new OkHttpUrlLoader.Factory(okHttpClient));
    }
}

public class UnsafeOkHttpClient {
public static OkHttpClient getUnsafeOkHttpClient() {
    try {
        // Create a trust manager that does not validate certificate chains
        final TrustManager[] trustAllCerts = new TrustManager[] {
                new X509TrustManager() {
                    @Override
                    public void checkClientTrusted(java.security.cert.X509Certificate[] chain, String authType) throws CertificateException {
                    }

                    @Override
                    public void checkServerTrusted(java.security.cert.X509Certificate[] chain, String authType) throws CertificateException {
                    }

                    @Override
                    public java.security.cert.X509Certificate[] getAcceptedIssuers() {
                        return new java.security.cert.X509Certificate[]{};
                    }
                }
        };

        // Install the all-trusting trust manager
        final SSLContext sslContext = SSLContext.getInstance("SSL");
        sslContext.init(null, trustAllCerts, new java.security.SecureRandom());

        // Create an ssl socket factory with our all-trusting manager
        final SSLSocketFactory sslSocketFactory = sslContext.getSocketFactory();

        OkHttpClient.Builder builder = new OkHttpClient.Builder();
        builder.sslSocketFactory(sslSocketFactory, (X509TrustManager)trustAllCerts[0]);
        builder.hostnameVerifier(new HostnameVerifier() {
            @Override
            public boolean verify(String hostname, SSLSession session) {
                return true;
            }
        });

        OkHttpClient okHttpClient = builder.build();
        return okHttpClient;
    } catch (Exception e) {
        throw new RuntimeException(e);
    }
}