Apple investors are losing confidence following the company’s latest executive shift. “Those of us who have backed Apple are worried,” Jim Cramer said on ” Squawk on the Street ” on Wednesday. The struggling tech giant announced Tuesday that its chief operating officer, Jeff Williams, plans to retire later this year . But until then, he will continue to lead its design team, Apple Watch engineering efforts, and other health initiatives. Sabih Khan, a 30-year company veteran and current operations senior vice president, is slated to take over as CFO. These personnel moves are the latest at Apple, which recently lost a key artificial intelligence executive, Ruoming Pang, to Meta Platforms and saw a chief financial officer switch in January. “Apple has to not have anybody else leave for a while. They should have people like Jeff Williams, if he’s going to stay for the Watch, have him stay years, because we just are worried,” Jim said. Jim’s concerns are well-founded. While Apple shares saw a record-high close of $259 on Dec. 26, 2024, the stock started the new year under pressure. Like many stocks and the overall market, Apple hit a 2025 low in April before President Donald Trump paused his “reciprocal” tariffs. Year to date, Apple has lost nearly 17% versus the S & P 500 ‘s more than 6% gain, as of Wednesday afternoon, and last week’s record highs. AAPL 1Y mountain Apple 1 year Apple is unfortunately between a rock and a hard place lately, with challenges stacked at its doorstep. This includes criticism from the White House. President Donald Trump has been pressuring Apple to make iPhones in the U.S. While most iPhone production is still in China, Apple has moved some of it to India. “With all these new advanced manufacturing techniques and the way things are moving with AI. It’s inconceivable to me that [Apple CEO] Tim Cook could not produce his iPhones elsewhere around the world and in this country,” White House trade advisor Peter Navarro told CNBC on Tuesday. In May, Trump threatened Apple with tariffs of 25% or more. Separately, he told Cook, “I don’t want you building in India.” In February, Apple committed to spending over $500 billion in the U.S. over the next four years, with a new Texas factory and other facility expansions as part of the plans. But a full iPhone production overhaul would be difficult and quite costly, according to analysts, noting that a fully American-produced iPhone could have an estimated price tag of up to $3,500. Jim on Wednesday defended Apple, arguing that Trump’s ire should be “restricted to companies that are bad actors. … Can we just recognize that Apple is a gem?” He added, referring to the iPhone, “It’s the product that everyone around the world loves.” Also on Apple’s plate of troubles is its AI strategy. The company is lagging behind its big tech peers. The simple solution to its AI problems, according to Jim, would be for Apple to “go buy Perplexity” to get back into the AI conversation. (Jim Cramer’s Charitable Trust is long AAPL, META, MSFT, NVDA. See here for a full list of the stocks.) As a subscriber to the CNBC Investing Club with Jim Cramer, you will receive a trade alert before Jim makes a trade. Jim waits 45 minutes after sending a trade alert before buying or selling a stock in his charitable trust’s portfolio. If Jim has talked about a stock on CNBC TV, he waits 72 hours after issuing the trade alert before executing the trade. THE ABOVE INVESTING CLUB INFORMATION IS SUBJECT TO OUR TERMS AND CONDITIONS AND PRIVACY POLICY , TOGETHER WITH OUR DISCLAIMER . NO FIDUCIARY OBLIGATION OR DUTY EXISTS, OR IS CREATED, BY VIRTUE OF YOUR RECEIPT OF ANY INFORMATION PROVIDED IN CONNECTION WITH THE INVESTING CLUB. NO SPECIFIC OUTCOME OR PROFIT IS GUARANTEED.