Our Gemara on Amud Beis considers the relative legal severity of two different kinds of watchmen: The free watchman, and the hired watchman. On a simple level, the hired watchman has more legal liability and severity than the free watchman. The hired watchman is liable for theft, and forms of non-negligent loss, while the free watchman can claim the object was stolen and be exempt, so long as he takes an oath that he employed an expected standard of supervision and that he did not appropriate the object for himself. Yet, if it turns out that he lied, and he took the object for himself, he is now liable just as a thief, and must pay kefel, the double penalty. So in an interesting twist, the free watchman has one legal liability that is more severe than the hired watchmen. The hired watchman will never incur the penalty of kefel, the double penalty, because there’s never an instance where he can claim that it was stolen (burglarized) and actually be exempt via a false oath. Even if he claimed it was stolen, he would be obligated to pay for the loss in accordance with his responsibilities as a hired watchman, therefore he never could make an oath on this and incur the double payment penalty. This shows a technical stringency that is really not an overall stringency. In most situations, the free watchman has less liability, yet here only he can incur the kefel penalty. Because of this, there is a dispute about whether the free watchman is considered to have a side that is legally more strict than the hired watchman, which could disrupt a kal v’chomer derivation.
Tosafos offers a deeper explanation as to why this does not constitute a stringency. The reason is, the particular stringency of paying a double penalty, only stems from a root leniency. Remember, the free watchman is exempt from liability for theft, so long as he makes this oath. At its core, this a leniency, even if in one dimension he could incur a financial fine that the hired watchman will never incur, should he make a false oath that it was burglarized when it wasn’t. We see from this Talmudic analysis, that it is possible for one category to have technical stringency, but still be considered overall more lenient than another category, so long as those stringencies stem from a basic leniency.
This principle is used by Rav Yehoshua Hartman to explain a difficult Maharal. The Maharal (Tiferes Yisrael 39) asserts that the sin of making a false oath is in certain ways, even more severe than idolatry. To illustrate, he quotes a Midrash that offers the following metaphor. One province rejects their king and appoints another monarch, while another province does not technically reject the king, but is utterly contemptuous toward the king. Which province shall we characterize as more disrespectful? Even though, technically, the first province completely rejected the king and replaced him, intuitively we can understand that the second province committed greater disrespect in mocking their king. So too, while idolatry is utterly rejecting God, swearing falsely in God‘s name is more deeply disrespectful because His name is being invoked.
Rav Hartman asks, if so, why is swearing falsely written in the 10 Commandments after the prohibitions against idolatry? The Maharal (ibid 36) already established that the 10 Commandments are enumerated in order of severity. However, if we use the Talmudic principle discussed above, the logic is understandable. Even though in one aspect, swearing falsely in God’s name is more disrespectful than idolatry, it still stems from a core leniency. That is to say, idolatry at its root is an utter rejection of God, while swearing falsely acknowledges God’s presence and existence. True, because of that, to swear falsely in His name is an even greater disgrace than merely ignoring God, it also is ultimately not as severe as idolatry in the big picture.
We see from here that the measurement and impact of sin can be multivalent. Sometimes a sin, that is technically more minor, can be more severe, because of the implications and the relationship between God and the person. If the relationship is closer, and acknowledged, which represents an overall good thing, even a smaller sin can become a greater disrespect and rejection. This is true in all relationships, the deeper the connection, the greater potential for breach of trust and pain when betrayals occur.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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