Matt Sullivan•Michael McLoone-Imagn ImagesAdd Sporting News on GoogleTarik Skubal is heading towards his MLB free agency with likely plenty of teams lining up, ready to make massive offers to try and convince the two-time Cy Young ace to come to their franchise.Skubal might not be picky with his next landing spot, as the highest bidder will likely be the one team to land Skubal. He's easily the top free agent, and he is likely in store for a record-setting deal.As MLB.com's Mark Feinsand highlighted, Skubal actually might break two MLB records this offseason. Those two records? The average annual value and the total value of a pitcher contract might have a new record holder this offseason.How Tarik Skubal might break two MLB records with new free-agent deal"Based on conversations with executives and agents around the league, Skubal's next deal could exceed both," Feinsand writes on the AAV and guaranteed contract records.While Skubal might break both of those records, what would that actually look like for the player the Los Angeles Dodgers spent a lot of prospect capital to acquire at this past trade deadline?Well, speaking of the Dodgers, Yoshinobu Yamamoto's 10-year, $325 million contract is the current MLB record for the largest guaranteed contract signed by a pitcher, not counting two-way superstar Shohei Ohtani's $700 million deal.Exceeding that mark wouldn't be too difficult for Skubal, especially considering the other record that he has a real chance of breaking this offseason.MORE: Dodgers facing tricky question over Shohei Ohtani's future as a two-way playerMax Scherzer and Justin Verlander are tied at $43.33 million for the highest average annual value (AAV) for a pitcher in MLB history. Skubal might break that record, too, this offseason.So, with the AAV and total guaranteed contract records for a pitcher both potentially being broken, what could a deal look like?If Skubal were to get a deal worth $44.5 million per-year, an eight-year deal would put him at $356 million total. That would break both records, while not being too egregious a contract.While there's no telling where Skubal's final contract number will wind up, one thing seems clear: Skubal is looking likely to break at least one MLB pitcher contract record, if not two, this upcoming offseason.More MLB news:Yankees predicted to replace Jazz Chisholm with $12M two-time Silver Slugger winner, 4x All-StarAstros have 2 clear trade candidates during MLB offseasonPadres 3.21 ERA postseason hero predicted to land huge $120M contractMariners manager candidate backs out of running for lesser job with PhilliesCubs' 26-HR outfielder gets underwhelming $66M contract predictionMatt SullivanMatt Sullivan is a freelance writer for The Sporting News, predominantly covering MLB. Matt is a native of Pennsylvania and has worked with Athlon Sports, Last Word on Sports, and other outlets.