Hugh Rockoff does a 72 pp. deep dive on Milton Friedman on bailouts. This is an excellent paper, as he also considers Friedman's columns and spoken words over the years and he also fleshes out Friedman's thoughts on what we now call "shadow banks" (he worried about them). Friedman was willing to accept a fair number of bailouts, here is one excerpt:
And more speculatively:
I recall being excoriated in 2009 for suggesting that Friedman would have endorsed some version of the bailouts of that time.