I tend to think McConnell is fairly overrated, I haven’t seen a lot of evidence of any Republican congressional leader, in the House or Senate, really had any sort of master-tier political abilities since Newt back in '94. Note that I put a time date on Newt because he devolved into stupidity and even ruin for his party in the House in a few short years, but the '94 Contract With America was undeniably a watershed event for the party and the country and was significantly the vision of one man (Newt.)
A lot of things that McConnell is considered a “Chess player” over, are actually just him doing exactly what his caucus wants him to do, which is a pretty obvious behavior of a leader in either of the two houses. Up until the late 2000s, the GOP still had enough traditional “mainline” conservatives and even a number of liberal and moderate Republicans in the ranks that for a majority leader to maintain support of their caucus they would have to be willing to negotiate and keep certain entities and groups happy.
I certainly don’t think McConnell is a dummy or anything, but I don’t think he plays the hardball he does because he’s so smart and previous Republican leaders were so stupid. I think the Great Purge of moderates and liberals from the party, the erasure of almost the entirety of Northeast “Rockefeller” Republican Senators, the election of multiple hardcore Tea Party Senators in the Southeast and Midwest, has lead to a Senate Republican caucus where simply the only majority that exists is a majority that denies the legitimacy of Democrats to run the country and is defined almost entirely by hatred of the left and various far right grievances.
This is actually markedly different than the Senate McConnell was elected to in the 1980s, and while McConnell was never a liberal, if you follow his early politics back in the 1980s there is some suggestion that man would have had trouble with this caucus. But McConnell has shown he cares more about the preservation of his power than he does any fixed political ethos.
Due to differences between the two bodies, the Senate Majority Leader has always been significantly weaker in marshaling the Senate than is the Speaker of the House. For an old school conservative Republican, who doesn’t naturally easily fit in with newer conservatives like Ted Cruz, Josh Hawley et al., McConnell has largely maintained his leadership by basically only having a spine on issues that the vast majority of his party are in lockstep over–for example getting conservative justices on the Supreme Court is a goal basically 100% of Senate Republicans share. There’s maybe 4 Republicans who care about continuing to promote “bipartisanship” and trying to find conciliation on significant swathes of public policy, so McConnell simply ignores them. He doesn’t fight with them or antagonize them; he just ignores them.
McConnell basically is riding a wave he doesn’t control, which is why I think portraying him as a chess master isn’t really accurate. I do think he is savvy, I just don’t actually think very many Republicans in his seat would be doing anything different, because he’s basically just doing exactly what his caucus wants. McConnell in some sense lucked into his position–I do not think he is doing anything Trent Lott (the Republican leader the resigned his leadership in 2002) would not have done. Lott and McConnell are the same age, and had Lott not “misspoken” with some racist nonsense back in 2002 he likely would have remained Majority Leader indefinitely, he held a super safe seat in Mississippi and Lott’s politics actually probably would have more naturally adapted to the Tea Party era than McConnell’s did.
After Lott you had Bill Frist as leader for much of the 2000s, but he was an example of a leader that would not have survived the Tea Party era, he was simply too much of that wing of the party that believed in trying to keep government functional, he could not have functioned well as a leader whose caucus would have expected him to try to implode government nonstop to undermine Obama. Frist had made a pre-election pledge to only serve two terms in the Senate, and in a shocking development for an American Senator–he lived up to the pledge and left office after his second term. I don’t know that he would’ve remained leader after the Tea Party wave hit in 2010 though, the party was moving in a direction he would not have been able to move with.
Unlike the House where you can win a somewhat tough leadership election like Boehner did, and then leverage the power of the Speakership to corral your party even when a lot of them dislike you, the Senate just isn’t setup like that. If McConnell had tried to take almost any other path than what he’s taken since 2007 (when he became minority leader) it is unlikely he would still be leader.