[3] Gillett acquired majority control of the television assets of Storer Communications in April 1987 from merchant banker Kohlberg Kravis Roberts,[4][5] and represented a valuation of nearly 15 times cash flow for the group.
[10] One of the Storer stations, WJW-TV, was frequently the subject of sale rumors due to their ratings strength and stability.
[11][12] WSMV was sold off in early 1989, leading Gillett to boast it shored up his company's finances[13] but the firm missed a October 1989 loan payment, prompting three creditors to ask the United States Bankruptcy Court in Delaware that SCI Television be placed in involuntary Chapter 7 bankruptcy[6] while SCI offered a debt for equity exchange.
[20] Gillett's financial pressures continued to mount after the WMAR sale was renegotiated to a lower price and a Denver bankruptcy judge denied any further extensions on a Chapter 11 filing.
[21] Facing lawsuits from multiple creditors including Apollo Partners, Allstate and Fidelity Investments, Gillett Holdings filed for Chapter 11 on July 26, 1991.
[24] Investor Ronald Perelman, regarded as a corporate raider and the owner of Revlon and Marvel Entertainment,[25] purchased majority control of SCI Television on February 17, 1993,[26] pushing Gillett out entirely.
[27] The transaction came through a bankruptcy court-approved Chapter 11 reorganization: Perelman's holding company MacAndrews & Forbes made a $100 million investment in SCI, which was still burdened by $1.3 billion in debt, in exchange for 53 percent of its equity.
On January 2, 2001, Gillett bought an 80% interest in the Montreal Canadiens and their home arena, Molson Centre, for US$185 million.
[34] Prior to the purchase, Gillett had shown interest in the Florida Panthers, New York Islanders, Ottawa Senators, and the Phoenix Coyotes.
[35] Gillett's bid initially raised fears that he might move the NHL's oldest franchise to the United States.
[41] Since October 2006, Gillett and fellow American Tom Hicks had been parties interested in a proposed takeover of Liverpool F.C.
On January 31, 2007, Dubai International Capital announced they had pulled out of the deal, giving Gillett the opportunity to buy the club from David Moores.
[43] On March 7, 2008, it was reported that Gillett had agreed to sell 98 per cent of his Liverpool stock to DIC,[44] but Hicks blocked the sale.
As a result of that we [my family] have received many phone calls in the middle of the night threatening our lives, death threats.
Mill Financial, based in Springfield, Virginia, reportedly refinanced a loan used by Gillett to buy a big stake in Liverpool F.C.
after they were unable to stop the Royal Bank of Scotland, which financed their original purchase of the team, from selling Liverpool F.C.
to Boston Red Sox owner John W. Henry’s New England Sports Ventures at a price that was lower than expected.
At the same time the Liverpool issue was occurring, Gillett's Richard Petty Motorsports fell into financial trouble.
On January 11, 2013, Hicks and Gillett finally decided to drop their case in the English law courts against Sir Martin Broughton, Christian Purslow and Ian Ayre, the three directors on the board of Liverpool F.C.