Former President Donald Trump's ambitious tax cut proposals have left Republicans scratching their heads as they ponder how to fund the renewal of expiring federal tax breaks. With the presidential campaign entering its final stretch, Trump is pledging to slash taxes on various fronts, including overtime pay, Social Security benefits, tips, and domestic manufacturing. However, these proposals come with a hefty price tag, estimated to cost trillions alongside the $4.6 trillion required to prevent tax hikes for millions of Americans when certain portions of the GOP's 2017 tax cuts expire next year.

While Trump's proposals aim to secure support from specific voting blocs, such as seniors in Florida, service workers in Nevada, and hourly employees in the Rust Belt, they have put congressional Republicans in a delicate position. Rather than focusing on renewing the 2017 tax cuts, which Trump supports but rarely emphasizes, Republicans find themselves grappling with the feasibility of his new proposals. Many Republicans have refrained from discussing the plans in detail, acknowledging that Trump is making promises they cannot deliver on.

Sen. John Cornyn of Texas, a senior tax writer running to replace Mitch McConnell as the Republican leader in the chamber, acknowledged the challenge of bringing Trump's proposals back to reality. "I understand that candidates, when they campaign, they float a variety of different ideas, but they can't all be true," he said. "So how do you bring them back to Earth? That's going to be a hard problem we'll have next year."

Trump's recent proposal to eliminate the cap on state and local tax deductions has also raised concerns among Republicans, as it contradicts a key provision of his own Tax Cuts and Jobs Act, which Republican leaders have staunchly defended. Moreover, experts from various political backgrounds have criticized many of Trump's proposals as poorly conceived, sparking doubts about their effectiveness.

Interestingly, some of Trump's proposals have put Democrats in an uncomfortable position. As they are hesitant to oppose tax breaks that benefit working and middle-class voters, Democrats have criticized Trump for pandering while highlighting the negative impact his administration's policies have had on hourly workers. However, they largely refrain from opposing the idea of exempting overtime pay from taxes. Presidential candidate Kamala Harris and other Democrats have even adopted Trump's proposal to exempt tips from taxes, despite concerns expressed by tax experts.

Trump's ability to set the agenda in Washington, even when he is not in office, is evident through his half-formed ideas floated on social media. This influence carries implications for future tax debates, should he win in November. However, critics argue that Trump's proposals not only face criticisms over their cost but also lack detailed implementation plans. Many of the proposals are seen as unfair since they would treat taxpayers in similar situations differently. For example, Trump's tip proposal would result in a significantly lower tax rate for restaurant waiters compared to those in industries where tipping is not the norm.

In terms of financing his plans, Trump has proposed higher tariffs and repealing green energy tax subsidies. However, even conservative-leaning budget analysts argue that these measures are insufficient to cover the costs. Additionally, some Republicans are skeptical of higher tariffs and eliminating renewable energy credits. With the government already facing a staggering $2 trillion deficit and soaring interest payments on the national debt, concerns about the viability of Trump's proposals continue to mount.

Although Democratic candidate Kamala Harris has also proposed significant tax breaks, Republicans are quick to point out that she has presented more comprehensive plans to cover the costs. Trump's off-the-cuff policymaking stands in contrast to Idaho Senator Mike Crapo, who is poised to become the Senate's top tax writer should Republicans regain control of the chamber. Crapo, known for his cautious approach, remains noncommittal when asked about Trump's flurry of proposals, stating that they are looking at various tax code fixes in preparation for the upcoming year.

As the campaign inches closer to the finish line, Trump's tax cut promises add complexity to an already intense debate on the tax code. With uncertainties around funding and implementation, both Republicans and Democrats face challenges in finding common ground on tax policies that effectively address the needs of American workers and businesses.