Montgomery recently had an online meeting with the Red Sox, Buster Olney of ESPN reports.
The veteran left-hander is the second-best arm left on the market behind reigning Cy Young Award winner Blake Snell, but neither pitcher appears on the cusp of a deal. Montgomery put together the best season of his career with the Rangers in 2023, posting a 3.10 ERA, 1.19 WHIP and 166:48 K:BB across a career-high 188.2 innings. He followed those numbers up with a 2.90 ERA in six playoff outings, playing a key role in Texas' World Series title.