Hollingsworth began running Congress in the 2016 cycle very soon after the Tennessee businessman, who had ties to several other states that weren’t named Indiana, moved to the Hoosier State. He initially seemed like an afterthought in the Republican primary to succeed Rep. Todd Young, but he attracted attention after he used his personal fortune to finance a huge early ad campaign at a time when his more established but cash-poor rivals couldn’t get on TV; he also got help from his wealthy father, who financed a super PAC that aired commercials praising the younger Hollingsworth and attacking the presumed frontrunner, Attorney General Greg Zoeller.

Another candidate, state Sen. Erin Houchin, saw where things were going and eventually went up with her own spot warning viewers that Hollingsworth was “a Tennessee millionaire who just moved here to try and buy our seat in Congress,” but she lacked the resources to sufficiently blast her opponent. Republicans said just before the primary that Hollingsworth had little ground game and few, if any, local allies, but that didn’t stop him from defeating Houchin by a convincing 34-25.

Republican gerrymandering and southern Indiana’s continued shift to the right made Hollingsworth the clear favorite in a district that had supported Mitt Romney 57-41 in 2012, but Democrats hoped that a weak GOP nominee would give Monroe County Councilor Shelli Yoder an opening. And for a long time, it seemed like it was possible that Hollingsworth’s flaws could indeed sink him, especially after the DCCC released an October poll giving him just a 44-42 edge.

National Democrats backed up their talk with action in the final weeks, and they ultimately spent $1.8 million compared to $1.3 million from their GOP counterparts. Hollingsworth also earned some ugly headlines in the final days when the Associated Press reported that legal papers he filed to serve as a “registered agent” for his real estate business obligate him to simultaneously reside in Virginia, North Carolina, South Carolina, Georgia, and Ohio. The Republican blamed it all on a clerical error, though he didn’t help things when, after acknowledging he’d lived in South Carolina, he refused to say where else he’d resided.

All of this, though, was far from enough in a seat as red as the 9th District. Donald Trump carried the seat 61-34, and while Hollingsworth badly trailed the top of the ticket, his 54-40 victory was still far from close. Democrats still hoped that the new congressman could be vulnerable in a very different political climate, but he won by a similar 56-44 spread in 2018 and had no trouble taking what would ultimately be his final term.